Blogs

Today was a great day!! My cast is now complete off. My thumb still feels a little odd but the dr said there will still be a lot of improvement. But the best part is that my sister and children threw me a surprise sorta household shower lol. Because I lost literally everything with the eviction because the way they went about it by the time I found out I only got 6 days before I was thrown out. I wasn’t able to really plan in a way that allowed me to save anything because I just panicked for those 6 days. But the landlord over these apartments was very difficult and a lot of crooked shit was going on. But after I was gone she ended up getting fired over another incident when a woman’s husband died. This woman’s family was coming around for support but the landlord kept having their cars towed. It was ridiculous. But I went straight from the eviction into the situation I just got out of. I tried to keep what was going on from my children because it’s not their place to worry about me. I just want them to be happy and enjoy their life. It’d be hard for them to understand how situations like this can happen cause it seems like you would just leave. But I couldn’t. Plus my son would have took on the responsibility of pursuing his on kinda justice. I don’t want his life affected by it. It’s been hard enough to keep him from feeling obligated to look out for me since I’ve became single. That’s not his burden to carry. Plus the anger he would develop wouldn’t be healthy for him. Anyways it’s just been hard going thru all of this while making sure it didn’t hurt the people I love. But they all found out anyway cause this is such a small town. Plus it’s kinda hard to hide a cast and all. Since the police were involved and everything happened like it did everybody in town knows now. That’s why it’s gonna be so good to move to Kentucky. I have a lot more family there. It’s about a 4 hour drive up north. But now I don’t own anything or have anything that I’ll need. Until today. They really pulled the surprise off well cause i literally had no clue. It’s usually pretty hard to keep stuff from me but they sure did lol! I was in shock! I got so many things. All household stuff and furniture. They really went out of their way to make this special for me. They had all my favorite foods and was playing all my favorite songs. Today was one of the best days of my life. I was truly blessed with the best kids ever!!!
It’s just not safe at all to post provocative pics on the internet. I know it can seem harmless at first cause it’s like flirting. The guys are all about it. They’ll keep on cause they wanna see. And it’s fun to wanna be seen. Being female imo is a privilege. And maybe there’s one or two you wanna show. It’s easy to get caught up in it and forget that the entire world could also be watching.

It’s all fun and games until Billy Bob pops up in your inbox because he likes to eat pretty girls. Literally. And he actually has his own personal collection of pics of you that he’s been collecting for ten years….pics that weren’t all in one place. This means he’s had to of been following you for a good while now. Talk about eerie af. And guess what about all those guys that wanted to see??? They no longer give a fuck now because they’ve already seen. So this will just give them something else to mock about you. Because no one’s gonna give a fuck about your pretty girl problems because now you’re just some whore that all their friends can make fun of. It can be like this on any site. It’s not specific to here. I’m talking in general but women need to think about who they give their attention to and what they put out on the internet. People can disrespect the fuck out of you just because you opened up to them. It will always be justified in some way or another and will always be all your fault. It’s a great way to end up really in danger. Trust me. I just went thru two years of hell and couldn’t even get myself out of it because of how ashamed I felt because of how a lot of people are nowadays. No one is coming to save you and no one really gives a fuck what happens to you. We gotta learn to look out for our selves and remind ourselves often that no man is worth it. Know your worth and respect yourself loudly. Because people don’t really respect each other anymore. They just don’t.
Wow. Just overall over my life circumstances. And I know I should be grateful because it’s nowhere near as bad as it could be. But fuck man. I just want to disappear sometimes.
I wished that I had never talked about what all I just went thru on here. I wished I never brought that here. It’s just the situation had me really isolated so I didn’t have a support system, but I still wish I’d never opened myself up like that on here. It is best to keep your personal life off of here, especially when you’re going through something extremely traumatic because you’re really taking a huge risk of making it so much worse by opening yourself up to strangers on the Internet. It’s not what this place is for. It was my fault cause I knew better. It’s just that my thinking was just so messed up because I was going through so much. I was trying to make something I could lean on out of nothing. Ive noticed lately how wrong people take me and how wrong I’ve been about others. So much does get lost in text lol. Thats why it’s just not a good idea to really depend on anyone for more then just banter. We really don’t even know each other actually lol if you really think about it. I was stupid, but lesson learned. I always have to learn everything the hard way lol

Some of yall have been great❤️ but this was too serious to be stressing yall with. I’m sorry
I just want to want something that I can actually have. Just having something that I really wanted would be so amazing. I guess my perspectives are a little skewed. I am begining to feel hope again finally tho. I see people building their own house it’s just baffling to me considering how they must feel. I can’t imagine getting to create the environment you’re gonna be living in. I can’t imagine having a husband that actually enjoyed seeing me happy instead of getting mad. I’ve gave huge chuncks of my life to the shittiest men. Everyone of them are now in prison. That’s not something I’m proud of. I hate that it took half of my life to teach me this lesson lol. I never got to look at my life as something that I could make. I never got to decide and really choose anything. I didn’t even know what I wanted. Everyone I slept with got me pregnant except one. I was just trying to make each relationship work so my child would have a family. Now I know what I want but I’ll never find it at my age. I wanna make someone happy. I wanna be someone’s everything. I wanna be someone’s biggest fan. I wanna to really take tho vows seriously. I wanna make my own vows to someone and commit to forever with them. But I want the same in return. I’m so done with projects. It can’t be based on feelings cause feelings are fleeting. I want someone that I can be mad and not be able to stand sometimes but still have no doubt that they are my person and vice vs. But these are goals people start out with in their 20’s. I feel like I’m just starting but now it’s already over. So I’ve just prepared myself to be ok being a alone. I’m just gonna work on myself and focus on being the rock that my children need. I’m gonna make a home that can be their place that they can always come home to. I’m gonna work on my faith and become who God created me to be. And about my addiction I’m ok with taking one suboxone a day for the rest of my life. I’ve just gotta snap out of survival mode and start living again.
The brain’s reward system is also what reinforces survival relevant behavior.
It involves the same mechanics of the brain involved with addiction. Dopamine isnt just a pleasure juice. It’s also a prediction and motivation signal. It whispers “this matters so come here”. It’s what drives the reward system in your brain that enforces the actions involved with your behavior’s. But the reward system does not force behavior. It biases motivation. This allows us to make choices, develop morally and form habits
But drugs can hijack this system by disrupting your dopamine baseline. So this means that a system designed for attachment and meaning can also be exploited by chemicals, power dynamics and shame regulation and social exclusion. So I’ve been thinking…since we are relational beings then a relational nervous system is coherent with that design. From a theological perspective this doesn’t reflect a flawed design but a very vulnerable one.

Humans are created with infinite desire because they are oriented toward infinite fulfillment. In Confessions St Augustine wrote that the human heart is restless until it rests in God. Neurobiologically the reward system keeps seeking. It updates your expectations. But it does not allow permanent satiation. This perpetual seeking could reflect a design toward transcendence or just simply an adaptive survival circuitry or maybe even both. It depends on your worldview. I believe in God. So imo the reward system exists so humans can move toward what gives life…biologically and spiritually. It is not a trap. It is a guidance system.

So since heaven is the final state of redeemed humanity then Im thinking maybe this implies that we will finally have a perfected reward system. I don’t mean anesthesia. I mean no distortion…no compulsion….no misdirected attachment….no scarcity anxiety. It would be like the intellect finally seeing the ultimate truth. The will finally at rest in ultimate good. Desire is fulfilled without annihilation. I’m not saying the reward system would be hyperstimulated. I’m saying it would be fully satisfied. With no craving loop….no dopamine deficit state…..no compulsive seeking. The seeking system would finally reach its telos. For the rest of eternity. In heaven we are gonna finally find our fix that last forever and we will never develop any tolerance.

I’m being speculative of course but I still can’t help but imagine how great that would be.

He’s gonna return what the locust have taken❤️
We teach people how to treat us by what we tolerate. Through dealing with my ex and his family I learned that lot of people don’t really appreciate kindness. They only recognize boundaries and consequences. They mistake restraint as weakness and perceive grace as permission. The more they get by with crossing the line without facing consequences the more ok they become about crossing the next one. This leads to someone’s kindness getting exploited. This is very depleting. Constantly accommodating someone who doesn’t reciprocate with respect can produce resentment…exhaustion and eventually emotional shutdown. It’s an imbalance. One person gives…forgives…understands and accommodates while the other person just keeps taking and exploiting them. The exploiter becomes entitled and feels validated because there’s little resistance. The kind person starts doubting themselves. They become convinced that they’re the problem when the real issue is that they’ve just been conditioned to tolerate too much.

But kindness is NOT a weakness. Forgiveness is NOT permission. And having a good heart doesn’t require having no boundaries. Actually boundaries are healthy.

Someone who genuinely respects you will generally respond to a reasonable boundary by adjusting their behavior. But someone who was just trying to benefit from your lack of boundaries will probably just respond with anger…accusations or attempts to make you feel wrong for just trying to protect yourself.

One of the hardest lessons I’m still trying to learn in life is how to remain compassionate without getting exploited. But it’s a necessary skill that we all have to acquire. We shouldn’t have to become hard hearted just so we can become harder to take advantage of.
Hi there Bluelight community. I'm here to give you a fairly succint idea of what is going on here in Clark County and for that matter, my life. As those of you know who have followed my blog, this all started with a break-up back in November and I had to start from scratch in a world that had become more harsh than what I had left. I ended up taking a job offer in Nevada. I felt like I wanted a change, so I did it. I ultimately regret that decision in most ways, though I do know that my destiny is ultimately out here, even if I do not yet know what that is.

Nevada and Vegas are very conservative. They are dependent upon tourists and it is thus, not a friendly place for those with addictions and issues with homelessness. Since I have gotten here, things have gotten worse for all of us Americans and those abroad. I have had some pretty rough news. My primary job is going to have a major funding shortcoming. I still have a job at present, but my work is no longer able to pay for a health plan for all of us. If you think this is ridiculous, try getting a letter in the mail telling you your coverage ended a week ago. Just like that. Apparently, they had sent another letter to my old residence here and I didn't receive it. I wasn't made aware in-person by anyone at my work.

I'm already having a very hard, more like impossible time managing the cost of living out here. I have Lupus, I take medicine, I am on Methadone and until I can get another insurance plan, I now have the added cost of ~$70/week 210/month for the clinic, which had been covered under my insurance. I take multiple medicines. You can love me, hate me, demonize me for it, but that is how it is. Vyvanse - ~120, Gabapentin ~35, Clonidine ~15... I recently started a biologic and I'm just straight up forgetting that one for now... it would be hundreds.

Next earthquake, I arrive at the clinic the other day to find only one nurse on duty. There are always two and we usually share pleasantries for a moment at the window. The other nurse tells me the other nurse no longer works there. She told me they are letting people go due to lack of funds. In her own words "she doesn't know what's gonna happen". Rumor is that the clinic will close and everyone will be forced to go to a different clinic ~90+ minutes away by bus. The only reason I am concerned is because the nurse was let go and the other nurse seemed genuinely concerned for myself and everyone else there, telling us to "be prepared". That last quip ruined my entire fucking week. "Be prepared".

So... I am now desperately trying to get a hold of SR to attempt to do a quick withdrawal from my Methadone. I have a fear that we are on the general chopping block. Like everything else that is getting chopped, social work, schools, medicine and who the fuck cares about the people at the clinic, they're a bunch of do-nothing low-lifes anyway. I'm sad to say, few people would bat a tear at the immediate hell we would be thrown into.

Judging by the behavior of the police, the general public and most people, I feel now under the gun to be free of this medication before it gets to a point where I am just left with nothing and no plan. You understand, if I were forced to the streets and had to withdraw from all medications simultaneously, I would off myself... I am not being dramatic. I am not looking for attention. I am just saying what many people in my position are thinking right now. The idea of going through this is antithetical to everything that I know I can easily handle.

If I lose my job(s)... I'm done. If I lose my medications... I'm done. If I cannot get insurance soon, with what money, I don't even fucking now... I'm done.

This is not a post for sympathy guys. It's a sad fact, I'm staring down the maw of a terrible fucking beast right now, as we all are. I have received a wake up call. I am now setting my sights on getting off Methadone or at least consuming a very, very small dosage I can easily acquire sans clinic. I am going to initiate an attempt with this SR stuff as soon as I have the spare bread to afford it, which is still a month out, as I owe too many people in my life for different things. That is the problem, see, I am already begging and borrowing just to survive right now. You can't live like that forever.

I do not have enough friends or family (who will help in this way) to call on at this point who could make a difference for me. To make a difference would take something that I know pretty much nobody reading this has. My clients are homeless. My coworkers are becoming homeless themselves, transitioning to their cars (so fucking sad) in the 110 degree heat. We are all getting to the end of our ropes. I do not know what this will look like for them. I know my situation with medicaiton is my own problem. I could have started doing this a long time ago, but I didn't. I could've gotten clean sooner, but I didn't.

I am concerned for myself, but also alm of the other people that are going to be affected by these reductions in services. When Russia invaded Crimea back in 2014 they made Methadone illegal overnight. Everyone just showed up in the morning to get their shit and the doors were locked. My understanding is, no warnings, no tapers of any kind. As you might expect, some lost their lives in a variety of ways as a result of this sudden, immediate hit. The bus is $3 here one way and $5 if you're coming near the strip.

I know it is a sad fact, but as we know, it is survival of the fittest when meat is thin and some people get trampled.

Political winds are shifting, maybe. This Presidency has not valued rule of law up until now. Besides, they have two years left with which to continue destroying the country.

You have to have hope though. There is always the possibility that we can get out of this. It definitely will take unity so I am not going to shit on any one's beliefs as that is the problem more than anything, because if we can't agree, nothing happens.

I'm just not really sure at this point guys. I pray every day that at least my life will be able to make a difference in this world somehow before my time is up. I spent so many years living for myself, thinking I understood love. I was a fool. So many wasted years. I get to experience my quest for sobriety at the same time the world starts ending (Trump's first term). I wish I could go back to Cambodia or Iraq and smell the food, touch the poppies, look the people in the eye instead of looking right through them with my dope eyes. I wish I had had time to be a better person than I was, but I can't go back now.

It has been hard guys. I'm coming to the end and there is no obvious path to take that leads me to salvation. I have two jobs. I have no time for myself. I am being broken by the stress of my job, homeless people disappearing, in fear for their lives from the police meant to protect them, the destruction of everything that I felt made humanity truly great... Now I get to watch my fellow man sacrifice the weak for their goals and I am not strong nor smart enough to stop them. Like I said, I pray at least that I will be able to use my life to make a difference, not for myself, I have been selfish my whole life, I want to give my life for something good.

I wish things were better. I'm gonna be around for the time being, but as things keep falling apart, I question how much longer I'm gonna be able to do anything that I love for much longer. My greatest hope is that I will be able to get off this shit in time to be useful for what is coming, because something is coming. I love all of you guys. 13 years of my life were well-spent on these forums. You all helped show me what love truly means and I will always be grateful for the opportunity to help and be a friend.

Love,

@Keif' Richards
I loved it on here cause I could flirt and be feisty. I could let my inner ho out🤣 but I think it’s gave people the wrong impression of me. But dang it’s just been so liberating. I hate feeling like such a closed off bitch in rl. It’s just different when people have real access to you. You have to behave differently. On here I can have fun cause no one can actually touch me. If yall could actually get your hands on me I wouldn’t be throwing my ass out there. But I think I’ve took it too far tho. I’m trying to settle down lol but it’s been like having an alter ego for me so I’m kinda addicted to being bad on here.
  • Locked
Dear Lord our Savior jesus christ please help us right now. Please please please help Now.

I don't beg or do I want to. I'm begging for help and strength this time. I have been holding

out and just being as thankful as I can. I can't anymore. Help us please. All of us. Especially

the ones sincerely trying to plead for that extra strength. Not just the ones whining and moaning

that they should be Entitled. For what ever sick shit it is that they choose to tear someone else apart for their own programmed Pleasures. The whole country was in Vietnam and all of them aren't trying to gouge someone else's eyeballs out AND BREAK THEIR FUCKING NOSES because you look at them wrong or say the wrong WORD. Now please help I am begging. I am crying out because no one

will do anything except for this and mal. Please protect us from this bullshit and give us the strength

to walk away better and for us to have that safety assurance and dignity with proper surroundings to do so. They will stop

at nothing for that blow job, last fuck in their life or a power peep to manipulate with their own story

for any and I mean any kind of power and control for the last fucking laugh to call someone a stupid

Cunt to make someone into someone the stupider piece of shit for the last word and fucking revenge that they can

get. And please God forgive me for Hating because I am truley filled with it and will be untill the fucking

day I Die. I pray that everyone that gets manipulated controlled by someone will stop at nothing to has the last goal in

life to have the Power over someone esle for their own sake of exploding it's balls in someone else is able

to finally rid theirselves of that sickness and them and that they go Fuck themselves away from us Forever.

I hope that you find a safe shelter and the help also to rid yourself of such Filth in Life and to do better because you can and please know that you will too.

They will lie manipulate others make up their own stories. Tell others that you are the sick insane feeble Bishhhh and believe every word and story that they make up to be the best that they can by lying to everyone and themselves and US and the only and ONLY thing that we can do is to get as far away from this

as possible and never ever ever look back and ever fall for being a victim Again. !!!!!!!!!!!!!!!!!!!!!!!!!!!!!

And then laugh about it because that's all they got and know and it's the last word and pleasure that at least

will be something something .... anything to get them off. Get the fuck away from those useless pieces of

existence that are still sucking the air that I can have instead. You know what .. I have hate enough to

wish until the day I Die and then thereafter that they get stuck down because I Don't Give One Shit Or

Fuck about thier kind or Ever Ever in the history of my existence ever will. Get away from him Get Away

from him I beg you and pray for you as well. !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! GET IT. DO YOU GET IT NOW.

Some of them can be very sick and IT WILL NEVER EVER EVER NEVER CHANGE. CUT OFF ALL

CONTACT. FIND SOMEWHERE TO GO. AND HIDE MOST LIKELY. And most important make it the

Safest place possible for your own Safety and Well Being. Because they will never stop and YOU will

continue to be Crazy for the rest of your entire life and then some. Get Away and Stay Away is the Only

thing that you can do. You have to take care of YOU because everyone else is going to use you BECAUSE THAT IS WHAT THEY DO. And all that they do. As in it is the whole purpose of their existence.

It's to laugh at someone else and to tell them that they are a CUNT when it counts the most.

God Lord Savior be on our Side right now. It is all that we have LEFT. aND that we will ever know

from now on. And they are happy and fulfilled and you are not. So please Lord reach out and help us

now. These are my LAST words Forever. A Fuckingggggggggggg Jesus Christ lord and fuckingggggggggggg men SAvior.


FUCK THEM and you know what they can Do. I SURE DO ! And will Die sayin IT.
today is a day i have dedicated to importing more of my cd library to itunes
i have a few hundred left and im trying to get as many as possible saved today
so yeah its very tedious so thats where the alcohol comes in
i had a small glass of popov vodka mixed with grape fanta earlier and thats fully kicked in and i might have another later
so yeah thats my day today
have fun psychonauts
I love you brother. I'm sure you already know but I had my first kid on May 31st. A son. We named Carter James. James I picked out to honor you. I still miss you dude. The permanent quality to death is starting to trip me out. Like that's it. Draw a line under July 2023. Before and after. As in your here but now your gone. I only just realized how much this fuck3d me up.
"Witchcraft Revival"

“Blue Fire”

NR4VMM-GLC4HP9K

“Red Fire”

NR4VMM-GLC4DP9K

"Black Fire"

NWAV8E-ZZZLKZUR

"White Light"

NMWJSH-X8JKXZYW
Hello Everybody! I hope everyone is hanging on, surviving and finding ways to appreciate life despite the hardships we are all facing. I haven´t been on here enough the past month. I don´t need to paint the whole picture, we are all living it. My career in social work gets me 24.50/hr. I´m sure a lot of you are similar to myself. When you´re doing this kind of work, it is difficult to know how and when to ¨put it down¨. There is a lot of emotion involved in the day to day work, then you think about it when you get home; what you could´ve, should´ve done. I also have a second job so I have very little time for anything. When I moved out here a few months back, things were different.

It is such a harsh realization. When I got here, I was already feeling like I was living in the slow apocalypse of humanity. Obviously, things have just gotten much worse economically, politically and of course, socially. People show their true colors when they are made to suffer. It´s easy to care about others when you have everything in your life straight; money, health, relationships. For instance, Bluelight and all of you guys are of the most important, proudest parts of my life. Still, despite the importance of the work, I can´t make it on here to do the work, as I am being pushed. More importantly, I´m seeing the complete and total segregation of the ¨haves¨ and the ¨have-nots¨. The ¨haves¨ means a job, stable living situation and at least one but possibly two cars for a family unit. If you don´t have a car, don´t have a stable place and can´t partake in the consumer culture, you are actively being excluded by the rest of society.

We get to these places as a society because people decided loving one another, connecting, caring and sacrificing were no longer mandatory principles for living. Vegas is a tourist town that caters to this consumer culture, This makes those that can´t spend antithetical to the system. For instance, I work right near the strip. While the strip is ¨outside¨ technically, you will notice that there are clear choke-points for entering and exiting the area which are staffed with beaucoup cops. Let´s just say, the Meth guy with his shopping cart full of garbage is not going to be on the strip for long if he gets there at all. Mass Surveillance is crazy. My understanding is that the strip, including the area were I work is completely and totally surveilled with everything from license plate readers, facial recognition and so on.

Some pretty terrible developments at the shelter.... try to follow me here.

The other night, we had an overdose in one of the stalls of the male bathroom. This is not extremely out of the ordinary for us. We gave him 3 narcans and called EMS. They often are unable to come or show up way too late to be effective. They are overstretched. Well, this time, the cops show up. Now, we have an insane time getting the heat to show up for anything, yet here they are. Two units and at least for uniforms. Even seeing the cops roll up... I didn´t know what was going down but I already had a bad feeling in my stomach.

We have overdoses regularly and nobody ever gives a shit. Well, tonight the cops are insanely concerned about the possibility of loose Opioids/Fentanyl being present in the facility. They were concerned that another resident might accidentally ingest some and overdose. This lead to the entire shelter being cleared out in the middle of the night. Dozens and dozens of people. It is ~2:00am at this point. Turn the lights on, wake everyone up, tell them they have to go outside. Naturally, some of the guys give the cops attitude. The looks on the faces of the cops when they got attitude was frightening. They were not pissed. They were not annoyed. They were not angry. They looked at them all almost with a knowing, almost amused expression as they watched everyone go outside.

While people are shuffling out, a lot of the ladies are actively saying ¨shut the fuck up!¨ to their men. The ladies are visibly afraid of the police. They are not afraid of getting arrested. They have the most primal fear of all in them; the fear of the unknown. Homeless people disappear here everyday. Jails, hospitals, morgues... a lot of them are just gone. Sure, some of them overdose and die in anonymity, but not all of them. My clients know something is wrong, but nobody knows the true extent of whatever is actually happening. If you ask me straight up, I´m just gonna say right now that I believe the homeless are actively being targeted and removed and I feel law enforcement is directly involved. I don´t care who I piss off by saying that. I have just seen too much weird shit to believe everything is normal.

We end up standing outside for over 2 hours. In this time, many of my clients choose to leave instead of standing outside on the pavement. By the time we are let back in, half of the clients have disappeared into the night. What´s worse, policy would prevent us from taking them back in even if they returned. The following night, we had lost ~15% of our regulars who have yet to return. For those who cannot read between the lines, I am implying that the cops are involved with deliberately making the shelter unlivable for clients. It is not legal to sleep on the street in Clark County. You can technically be arrested, especially if you have a tent. So, the cops have now separated these vulnerable people from the relative safety of our shelter and us people who care about them. Now hey are out there in the night and fuck knows what will happen to them.

My laptop broke down for the final time and I have not been able to replace it yet. I only have steady access to a computer when I am at work, so I´m going to do my best to get some BL in in my down time. It is really tough out there. I know a lot of you, like me, are making decisions like ¨should I buy food or medicine¨. The cost of living here has gone up to the point where, by working two jobs, like 55 hours weeks at least, I´m still essentially going broke. I am sad to say at this point that the amount of money I make is really not sustainable for many of the things I have become used to. Frankly, I worry every day now that our time is limited with my non-profit. There is little to no sympathy here for these people and the scarcity of money just makes it worse.

I am struggling right now trying to figure out how or what my life is going to become. On the current trajectory, I am just moving slowly toward oblivion like most of us are. Still, I try every day to find some joy in life, the people I work for and from my friends and family. Forgetting love and compassion is what has made us so terribly ill as a society. We can´t control the world, but we can control how we treat others. I have spent my life as a selfish asshole. I only hope that by the end, I will break even.

I will see you all on the forums. Sorry for the absence!
Effect of alkaloids of ololiuqui in man. Isbell, H., Gorodetzky, C. W. 1966. Psychopharmacologia, 8(5), 331–9. 10.1007/BF00453511

Effect of Alkaloids of [Ololiuhqui] in Man

By

HARRIS ISBELL and C. W. GORODETZKY

(Received June 11, 1965)

In 1941 SCHULTES reported that Indians in Mexico ingested the seeds of a wild morning glory, called [ololiuhqui], either in religious rituals or in the therapy of disease. The plant was identified as Rivea Corymbosa (SCHULTES 1941). MacDOUGALL (1960) reported that another variety of morning glory (Ipomea violacea, also known as Ipomea tricolor) was used in a similar fashion. According to WASSON (1963), the seeds of Ipomea violacea are more potent than those of Rivea Corymbosa. Because of SCHULTES' report, OSMOND (1955) ingested 14 to 100 seeds (chewed or ground to a powder) in a number of self experiments. He developed apathy, irritability, lack of energy and hypnagogic phenomena that disappeared after several hours. KINROSS-WRIGHT (1959) fed up to 125 seeds to 8 human volunteers without obtaining any subjective effects. ISBELL gave former addicts finely ground seeds of Rivea Corymbosa in doses ranging up to 6 g (approximately 300 seeds) and observed only slight sedation and nausea.

In 1960 HOFMANN and TSCHERTER (1960) reported the isolation of d-lysergic acid amide, d-iso-lysergic acid amide, and chanoclavine from seeds of Rivea Corymbosa. These authors took 2 mg of the crude extract of [ololiuhqui] alkaloids and developed dreamy states, with alterations in the perception of colors and objects. HOFMANN (1963) further reported that the seeds of Rivea Corymbosa contained 0.012 percent of indole alkaloids, whereas seeds of Ipomea violacea contained 0.06 percent. He also found that in addition to d-lysergic acid amide, d-iso-lysergic acid amide, and chanoclavine, the seeds of both plants contained elymoclavine. Lysergol was found in Rivea Corymbosa and ergometrine in Ipomea violacea.

Some information is available concerning the subjective effects of d-lysergic acid amide. HOFMANN (1963) took 0.5 mg of this drug hypodermically and reported fatigue, sedation, and sleep. SOLMS (1956 a, b) likewise found that d-lysergic acid amide caused decreased psychomotor activity, sedation, and sleep. ISBELL obtained similar results with d-lysergic acid amide in former morphine addicts. HOFMANN (1963) experienced tiredness, apathy, and "mental emptiness" after 2.0 mg of d-isolysergic acid amide. Elymoclavine elicits excitation and central stimulation in animals (YUI 1958), but ISBELL found that elymoclavine caused chiefly sedative effects in former addicts.

Law enforcement officers and garden seed companies in the United States have recently become concerned because of reports in the lay press that students, psychologists and maladapted persons of Bohemian habits ("beatniks") were ingesting seeds of cultivated morning glories sold in garden supply shops. Some of the persons who report they have used the seeds state they have also taken LSD-25, mescaline, psilocybin, or peyote. COHEN (1964) has reported one case of suicide following ingestion of morning glory seeds, and INGRAM (1964) has recently described a psychic reaction after eating 250 seeds that was sufficiently severe to require hospitalization. Thus fears have arisen that a new type of potentially dangerous psychoactive drug abuse might be arising in the United States.

Because of the varying reports concerning the efficacy of the whole seeds of [ololiuhqui] in inducing subjective effects, it seemed of interest to study the effects of the crude extract of alkaloids of [ololiuhqui] prepared by HOFMANN and coworkers, since use of the extracts would avoid differences in absorption and potency of different lots of the seeds. Such a study would also be valuable in assessing possible behavioral pathology arising from [ololiuhqui] abuse. A comparison of the effects of the crude extract of [ololiuhqui] seeds with those of a mixture of synthetic alkaloids compounded in the same proportions might also shed light on the question as to whether the alkaloids identified in [ololiuhqui] account for all the effects of the seeds. The purpose of this paper is to describe the autonomic and subjective effects of a crude extract1 of the alkaloids of [ololiuhqui] in man, and to compare the effects of the crude extract with those of a mixture of synthetic alkaloids2 containing the drugs in the same percentages as in the crude extract. In addition, the effects of both the crude and synthetic mixtures of [ololiuhqui] alkaloids were compared with those of LSD-25 and placebo.

-----------------------------------------------------------
1 We [are] indebted to Dr. A. HOFMANN and coworkers of Basel, Switzerland, and to Dr. R. BIRCHER, Sandoz, Hanover, New Jersey, for this material, which was an extract of the alkaloids of Ipomea violacea. The material contained (in terms of the percentage present in fresh seeds): d-lysergic acid amide, 0.035 percent; d-isolysergic acid amide, 0.005 percent; chanoclavine, 0.005 percent; elymoclavine, 0.005 percent; and ergometrine, 0.005 percent. Total alkaloids amounted to 0.06 percent. For details on the method of extraction and analysis, see the paper of HOFMANN (1963).

2 This mixture was supplied through the kindness of Dr. R. BIRCHER, Sandoz, Hanover, N. J. It consisted of 45 percent d-lysergic acid amide, 25 percent d-isolysergic acid, 10 percent ergonovine, 10 percent chanoclavine, 5 percent elymoclavine, and 5 percent lysergol. These percentages were calculated in terms of the bases and not the salts.
-----------------------------------------------------------

Methods

Subjects. Former opiate addicts who were serving sentences at the PHS Hospital in Lexington, Kentucky, for violations of the United States narcotic laws volunteered for the experiments. All were physically healthy males between 21 and 40 years of age, none of the patients presented any evidence of the major psychoses on psychiatric examination, all were familiar with the subjective effects of several kinds of psychoactive drugs, and all had been abstine frontm opiates for at least several months before the experiments were begun.

General Conditions. The experiments were carried out in the closed wards of the Addiction Research Center devoted to clinical research. The patients entered this ward the night before experiments were conducted and remained until the morning after experiments were completed. Observations were made by specially trained aides with long experience in observing the effects of psychoactive drugs.

Drug and Doses. Appropriate stock solutions of the crude alkaloidal extract (hereafter designated V-E-5), the synthetic mixture1 (V-E-6) and LSD-25 were prepared in one percent tartaric acid solution and refrigerated in brown bottles. Doses were measured into medicine glasses with pipettes and diluted with 15 ml of cherry syrup. The patients drank the mixture, rinsed the glass twice with water, and drank the rinsings. The cherry syrup served as the placebo. Drugs were always given at 8 a. m., with the patients fasting.

Observations. One hour before and 1, 2, 3, 4, 6 and 8 hours after the drugs were given, rectal temperatures, pulse rate, systolic and diastolic blood pressures and pupillary size were determined. Pupillary diameter was measured by comparing the size of the pupil with those of circles of known diameter, under conditions of constant light and accommodation. Measurements were made after patients had rested quietly in bed for 10 min.

In addition a questionnaire (Table 1) of 31 items was administered one-half hour before, and at 11⁄₂, 21⁄₂, 31⁄₂, 51⁄₂ and 71⁄₂ hours after the drug was given. The questions were selected from a questionnaire that has been used extensively in evaluating responses to LSD-25 and other psychotomimetic drugs (ABRAMSON et al., 1955). Short mental status examinations were made two to three hours after the drug.

Statistical Analyses. The results for all subjects were tabulated and averaged for each measurement at each observation time. These tabulations permitted identification of the time of maximal (peak) effect. The areas under the time-action curves for each measurement on each drug were calculated according to the method of WINTER and FLATAKER (1950) and means and standard errors calculated for the areas on each measurement for each drug. The significance of the differences between means was evaluated by the t-test for paired observations (EDWARDS 1964). The number of responses on the questionnaires were counted for each hour, for the entire time course, and for each individual question. Questions 3 through 31 were then ranked for each drug according to the relative magnitude of the total responses to each question, as shown in Table 1. Spearman rank order correlation coefficients were then calculated in order to compare the pattern of subjective effects (as measured by the questionnaire) of different pairs of drugs.

-----------------------------------------------------------
1 See footnote 2, p. 332.
-----------------------------------------------------------

Experiments

Preliminary. Before definitive comparisons could be made, it was necessary to determine the effective dose range of both the extract and the synthetic mixture. Two patients were tested at a time. The first pair of men received 0.5 mg (total dose) of either V-E-5 or V-E-6. The second pair of men received 1.0 mg. The doses were gradually increased in this step-wise fashion until 5 mg of both V-E-5 and V-E-6 were given. Temperature, pulse rate, respiratory rates and subjective effects, as measured by the questionnaire, were monitored in these experiments. Urine analyses, tests of liver function, and blood counts were unaltered in these preliminary experiments. Subjective effects began to be reported with doses of 2 to 3 mg, but were not intense even with the 5 mg dose. No serious untoward effects were observed with any dose. Doses larger than 5 mg could not be studied because of limited supplies of both mixtures. The data obtained in these dose-ranging trials are not presented in this paper.

Definitive Experiments. Six patients received at weekly intervals in random, order 5.0 mg of the crude extract (V-E-5), 5.0 mg of the synthetic extract (V-E-6), 1.5 mcg/kg of LSD-25 (as tartrate), and placebo. The data obtained on these 6 patients are presented below.

Results

The results are summarized in Tables 1, 2 and 3. The autonomic effects of the two mixtures were quantitatively small. As compared with placebo (Tables 2 and 3), neither V-E-5 nor V-E-6 caused any statistically significant (P < 0.05) elevation in temperature, pulse rate, or systolic blood pressure. V-E-5 did not create any significant mydriasis, but did block the diurnal miosis seen after placebo. V-E-6 caused a slight mydriasis. In contrast, LSD-25 was followed by marked increases in temperature, systolic blood pressure, and pupillary size. The synthetic mixture (V-E-6) caused significantly greater changes in systolic and diastolic blood pressures and pupillary size than did the natural mixture (V-E-5). LSD-25 created greater increases in temperature, systolic blood pressure, and pupillary size than did either mixture.

Compared to placebo, both the crude extract and the synthetic mixture caused significant subjective effects which differed qualitatively and quantitatively from those of LSD-25. These appeared 11⁄₂ hours after the drugs were taken, were maximal at 21⁄₂ hours, and had largely subsided in 71⁄₂ hours. The subjective effect most consistently reported was sleepiness (question 12, Table 1), plus the questions (1 and 21) dealing with general nonspecific drug effects. Neither V-E-5 nor V-E-6 were identified as being like LSD (question 6), marihuana (question 5), or cocaine (question 4). There were very few reports of distortion in sensory perception (question 11, 13, 19, 26 and 29). Hallucinations did not occur. Though not included in the questionnaire, nausea and headache were spontaneously reported by most patients. In contrast, LSD caused nervousness (question 8) rather than sleepiness, marked perceptual distortion (questions 11, 12, 19, 26 and 29), and "euphoria" (questions 14, 21, 25 and 28). LSD was frequensly identified as being like LSD (question 6), marihuana (question 5), and cocaine (question 4). Though not covered in the questionnaire, all patients receiving LSD had simple optical hallucinations (light, colors, patterns), and some subjects reported "true" hallucinations. Correlation coefficients indicate a significant positive correlation (i.e., a significant similarity) between the pattern of subjective effects of V-E-5 and V-E-6. However, neither V-E-5 nor V-E-6 had a significantly similar pattern of subjective effects to LSD.

Table 1. Number of responses by question

Drug and Dose
QuestionLSD 1.5 mcg/kgV-E-5 5.0 mgV-E-6 5.0 mg
totalranktotalranktotalrank
1. I feel the medicine342833
2. It is like a blank000
3. It is like a golfball027.548410
4. It is like coke918022.5021.5
5. It is like a reefer1216.5114.5021.5
6. It is like LSD1216.5022.5021.5
7. It is like dope027.5022.5021.5
8. I am nervous235022.587.5
9. I am hungry422.556.587.5
10. I am afraid719.5022.5021.5
11. The walls are moving1613022.5021.5
12. I am very sleepy125222281
13. Distances are changing1514022.5021.5
14. I feel very gay263022.5021.5
15. My mouth is dry1315105155
16. I am relaxed235271192
17. I feel silly2010022.5021.5
18. Time passes slowly422.5212.5113
19. Colors are changing2010310211.5
20. I am sad027.5310174
21. I am high271.5133183
22. Time goes fast621022.5021.5
23. My body feels light2010114.5021.5
24. I can think clearly027.5022.5021.5
25. I like the feeling227114021.5
26. People look funny1712022.5021.5
27. I have no appetite324022.5021.5
28. I laugh easily271.5022.5021.5
29. My hearing is keen21831069
30. My mouth is numb719.556.5211.5
31. I feel confused235212.5126

Spearman Rank Order Correlation Coefficients: 1. LSD vs V-E-5 rs = + 0.106; 2. LSD vs V-E-6 rs = + 0.134; 3. V-E-5 vs V-E-6 rs = + 0.8141.

1 Significant correlation at P < 0.05.

The figures under "total" represent the total number of positive responses to each question. The maximum possible number (6 subjects times 6 observations) of positive response is 36.

The figures under "rank" represent the rank of each question according to the relative number of total positive responses (i.e., rank 1 equals question with greatest number of total positive responses, etc.).

The number of responses to placebo were so small that data on placebo have been omitted.

Table 2. Results of comparisons of V-E-5, V-E-6, placebo and LSD-25 using the paired T-test

MeasurePlacebo vs V-E-5Placebo vs V-E-6Placebo vs LSDV-E-5 vs V-E-6V-E-5 vs LSDV-E-6 vs LSD
Temperature0.890.673.310.543.2215.271
Pulse rate1.641.313.7710.510.61.4
Systolic blood pressure0.852.144.1712.6514.113.11
Diastolic blood pressure2.172.712.362.9511.990.93
Respiratory rate1.390.580.50.441.371.05
Pupillary size1.034.6117.7312.9616.316.191
Total positive answers7.1719.58113.9112.4612.219.21

1 Statistically significant values (P < 0.05).

The figures in the table are the "t" values calculated from data on the same 6 subjects who received all drugs.

Table 3. The effects of the natural alkaloids (V-E-5) of [ololiuhqui], a synthetic mixture of alkaloids simulating those of [ololiuhqui] (V-E-6), LSD-25 and placebo

MeasurementPlaceboV-E-5, 5 mgV-E-6, 5 mgLSD-25 1.5 mcg/kg
Temperature1+ 3.06 ± 0.6+ 2.22 ± 0.74+ 1.66 ± 0.5+ 5.54 + 0.5
Pulse rate1+ 39.3 ± 17.3+ 68.2 ± 20.0+ 38.8 ± 18.0+ 79.0 ± 10.8
Systolic blood pressure1+ 37.8 ± 13.2+ 51.3 ± 13.7+ 92.0 ± 15.0+ 136.5 ± 15.9
Diastolic blood pressure1— 7.2 ± 13.6+ 20.7 ± 13.65+ 43.3 ± 16.7+ 60.5 ± 20.5
Respiratory rate1+ 16.5 ± 5.0+ 9.5 ± 2.4+ 11.9 ± 3.6+ 22.5 ± 8.7
Pupillary size1— 2.88 ± 0.41— 0.3 ± 2.3+ 4.92 ± 0.5+ 12.8 ± 1.8
Total positive answers25.8 ± 2.024.2 ± 3.330.0 ± 3.168.3 ± 5.8

1 Figures represent means ± standard errors of areas under time-action curves "degree hours" (temperature); mm hours (blood pressure); etc. A positive sign indicates an increase over predrug measurements; a negative, a desrease.

2 Figures represent total number of questions scored positively on the questionnaire that were not scored positively before the drug was given.

Discussion

Though both V-E-5 and V-E-6 caused definite subjective effects, the pattern of symptoms of the mixtures of [ololiuhqui] alkaloids was distinctly different from that caused by LSD. These mixtures had predominantly sedative properties and, in the doses used, were not "hallucinogenic". Our results are probably very similar to those of HOFMANN and CERLETTI (1961) since these authors experienced — like our patients — fatigue, sedation, and sleep. Similarly OSMOND (1955) reported apathy rather than hallucinations. Therefore it seems more appropriate to speak of [ololiuhqui] and its alkaloids as "sedatives" rather than "psychotomimetics" The results also agree with the sedative effects reported after d-lysergic acide amide (HOFMANN 1963; ISBELL; SOLMS 1956), d-iso-lysergic acid amide (HOFMANN 1963), and elymoclavine (ISBELL). The slight autonomic changes that followed V-E-5 and V-E-6 also contrast sharply with the spectacular autonomic changes seen after LSD.

There was no indication in these experiments that the crude extract of [ololiuhqui] (V-E-5) contained significant amounts of active substances not found in the synthetic mixture (V-E-6). In fact, V-E-6 caused significantly greater effects on pupillary size and blood pressure than did V-E-5.

Because the effects of these mixtures of alkaloids were relatively mild and were dysphoric rather than euphoric, the chances of abuse of morning glory seeds becoming widespread do not seem great. This view is reinforced by the paucity of effects observed in another group of addicts who ingested 6 g of ground [ololiuhqui] (Ipomea violacea) seeds (ISBELL). The number of seeds that would have to be taken to obtain the amounts of alkaloids equal to those used in these experiments is very great. The highest reported content of alkaloids in morning glories are 0.06 percent in Ipomea violacea (HOFMANN 1963) and 0.057 in the Pearly Gates variety (TABER et al. 1963). Using either of these figures one can calculate that a minimum of 400 morning glory seeds (8.7 g) would have to be ingested to furnish 5 mg of alkaloids. Since extraction of the alkaloids from the seeds would not be complete, even larger doses would probably be required. It is quite possible that the effects reported after ingestion of the seeds by maladjusted persons are due as much to suggestion from the social situation in which the seeds are used to the pharmacological effects of the alkaloids contained in the seeds. In addition, other drugs (alcohol, marihuana, etc.) that are frequently taken with the seeds may contribute to the marked mental effects that have been reported.

Summary

Five mg of either a crude extract of seeds of [ololiuhqui] or a mixture of synthetic alkaloids caused drowsiness in former morphine addicts but few other subjective effects. Perceptual distortion was reported only rerely, and hallucinations did not occur. In contrast, LSD-25 caused nervousness, perceptual distortion, euphoria and hallucinations. The alkaloids of [ololiuhqui] did not cause fever or marked mydriasis. [Ololiuhqui] and the alkaloids of [ololiuhqui] should be regarded principally as sedatives rather than as psychotomimetics.

References

ABRAMSON, H. A., M. E. JARVIK, M. R. KAUFMAN, C. KORNETSKY, A. LEVINE, and M. WAGNER: Lysergic acid diethylamide (LSD-25); I. Physiological and perceptual responses. J. Psychol. 39, 3—60 (1955).

COHEN, S.: Suicide following morning glory seed ingestion. Amer. J. Psychiat. 120, 1024—1025 (1964).

EDWARDS, A. L.: Statistical analysis for students in psychology and education. New York: Rhinehart and Co. 1946.

HOFMANN, A.: The active principles of the seeds of Rivea Corymbosa and Ipomea Violacea. Botanical Museum Leaflets, Harvard University 20, 194—212 (1963).

—, u. A. CERLETTI: Die Wirkstoffe der dritten aztekischen Zauberdroge oder die Lösung des ,,Ololiuqui-Rätsels". Dtsch. med. Wschr. 86, 885—888 (1961).

—, and H. TSCHERTER: Isolierung von Lysergsäure-alkaloiden aus der Mexikanischen Zauberdroge Ololiuqui (Rivea Corymbosa [L.] Hall. f.). Experientia (Basel) 16, 414 (1960).

INGRAM, A. L.: Morning glory seed reaction. J. Amer. med. Ass. 190, 1133—1134 (1964).

ISBELL, H.: Unpublished observations.

KINROSS-WRIGHT, V. J.: Research on [ololiuhqui]: the Aztec drug. Proc. First Internat. Congr. Neuropsychopharm. 1958. In BRADLEY, P. B., P. DENIKER, and C. RAUDOCO-THOMAS (Eds.): Neuropsychopharmacology, p. 453. Amsterdam, London, New York: Elsevier Publishing Co. 1959.

MACDOUGALL, T.: Ipomea Tricolor. A hallucinogenic plant of the Zapotecs. Bol. Cent. Invest. Antropolog. Mex. 6, Mar. 1 (1960).

OSMOND, H.: Ololiuqui. The ancient Aztec narcotic. J. ment. Sci. 101, 526—537 (1955).

SCHULTES, R.: A contribution to our knowledge of Rivea Corymbosa, the narcotic [ololiuhqui] of the Aztecs. Cambridge, Mass. Botanical Museum, Harvard University 1941.

SOLMS, H.: Chemische Struktur und Psychose bei Lysergsäurederivaten. Praxis 45, 746—749 (1956).

— Relationships between chemical structure and psychoses with the use of psychotoxic substances. J. clin. exp. Psychopath. 17, 429—430 (1956).

TABER, W. A., L. C. VINING, and R. A. HEACOCK: Clavine and lysergic acid alkaloids in varieties of morning glory. Phytochem. 2, 65—70 (1963).

WASSON, R. G.: Notes on the present status of [ololiuhqui] and other hallucinogens of Mexico. Cambridge, Mass.: Botanical Museum Leaflets, Harvard University 20, 161—193 (1963).

WINTER, C. F., and L. FLATAKER: Studies on heptazone (6-morpholino-4-4-diphenyl-3-heptanone hydrochloride) in comparison with other analgesic agents. J. Pharmacol. exp. Ther. 98, 305—317 (1950).

YUI, R., and Y. TAKEO: Neuropharmacological studies on a new series of ergot alkaloids. Jap. J. Pharmacol. 7, 157—161 (1958).

Dr. HARRIS ISBELL,

National Institute of Mental Health, Addiction Research Center, P.O. Box 2000,

Lexington, Kentucky 40501, U.S.A.
Die psychische Wirkung der mexikanischen Droge „Ololiuqui“ am Menschen. Heim, E., Heimann, H., Lukács, G. 1968. Psychopharmacologia, 13, 35–48. 10.1007/BF00401617

Translated from German by Claude.

The Psychological Effects of the Mexican Drug "ololiuhqui" on Humans

E. Heim, H. Heimann, and G. Lukács

Psychiatric University Clinic Waldau-Bern (former Director: Prof. M. Müller)

Clinical-Psychological Laboratory (former Director: Prof. H. Heimann)

Received August 31, 1967

Final version: February 2, 1968



Psychotomimetic Effects of the Mexican Drug "ololiuhqui"

Summary. The alkaloids of the third magic Mexican drug "ololiuhqui" — chemically closely related to LSD 25 — were studied in normal subjects in a laboratory situation. A standardized method (developed and applied before in testing other psychotomimetic drugs) included the following procedure: A short interview taken every 45 min was recorded on sound-film and then analyzed for changes in expression and motor behavior. A battery of psychometric tests also given every 45th minute was studied for trend-changes over time. Finally, symptoms reported by the subjects were divided into 8 categories, reflecting a spectrum going from autonomic side-effects to psychotic symptoms and alteration of consciousness.

The results indicate that the effect of the two major compounds, d-lysergic-acid-amide and d-iso-lysergic-acid-amide, determine the effect of the total alkaloids of ololiuhqui. With d-lysergic-acid-amide the clinical picture was one of intoxication with strong autonomic side-effects; with d-iso-lysergic-acid-amide euphoria, synesthesia, and altered time experience were observed. In small doses the response to total-alkaloids resembled that of d-iso-lysergic-acid-amide; in higher doses it resembled that of d-lysergic-acid-amide, i.e. a heavy intoxication with reduced consciousness and autonomic side-effects. Overall, there was little difference between the total alkaloids and the compounds of ololiuhqui.

Psychometric tests taken at each 45-min-phase also reflected the progressive intoxication: the performance in each of the five tests measuring the ability to concentrate was increasingly reduced, as compared to placebo subjects, during the time of observation. This is in contrast to observations on Psilocybin: here the psychometric results were worst after the first 45-min-phase, whereas changes in expression and motor behavior were greatest in the last of the phases, i.e. after 2–3 hours.

Not only are there no phase-dependent alterations with qualitative modification of the effects in ololiuhqui as compared with Psilocybin; in addition there was little evidence of typical alteration in consciousness and hallucinations as typically seen with psychotomimetic drugs like LSD 25 and Psilocybin.

In conclusion, ololiuhqui tested in normal subjects in a standard laboratory situation lacks the characteristics of the typical psychotomimetic drugs. It resembles more drugs like scopolamine and ibogalin, inducing a toxic psychosis.

Key Words: Lycergic Acid Diethylamide — Psilocybine — Psychological Interview — Psychometrics — Toxic Psychoses.



1. Research Question

Little verified information has previously been known about the psychological effects of "ololiuhqui," the third Mexican magic drug. The Spanish authors who described the use of the drug by the indigenous peoples in the 16th and 17th centuries mention that ololiuhqui numbs and confuses the senses (Bernardino de Sahagun), and that it leads to intoxication with phantasmal visions and demonic apparitions (Francisco Hernandez). Reko counted it among the magical poisons of the indigenous peoples and described a predominantly sedating effect. The identification of the plant called Serpent's Herb (cox-xihuitl) by the indigenous peoples was accomplished by Urbina and confirmed by Schulthes. It concerns the convolvulaceous species Rivea Corymbosa and Ipomea violacea. Hofmann and colleagues isolated six indole alkaloids from the seeds of these plants in 1960 and determined their chemical structure. Phytochemically surprising was the fact that such alkaloids — previously isolated only from lower fungi of the genus Claviceps — were demonstrated here for the first time in a higher plant.

Moreover, most of the ololiuhqui alkaloids had previously been produced semi-synthetically in the Sandoz laboratories, and they bear a close relationship to the phantasticum LSD 25.

The following alkaloids were isolated by Hofmann and colleagues (Fig. 1).

Little research has previously been conducted on the effects on humans. Solms found, using the semi-synthetic d-lysergic acid amide at doses of 0.75–1.0 mg s.c., lack of drive, indifference, need for sleep, and increasing clouding of consciousness, which after ½–1 hour transitioned into an arousable sleep that can last approximately 2 hours. He was unable to observe hallucinatory phenomena, though rather unpleasant neurovegetative disturbances occurred (hypersalivation, vomiting, dizziness, diarrhea). According to Osmond, the unchewed seeds have no effect (self-experiment by Reko). Osmond found, at a dose of 100 carefully chewed seeds of Rivea corymbosa, clear psychological changes: initially social withdrawal, apathy, and drowsiness, accompanied by a certain fascination with objects in the immediate surroundings, then drowsy sleep, which after several hours transitioned into a prolonged sense of wellbeing. Osmond's dosage amounted (according to our calculation) to a maximum of approximately 2.8 mg total alkaloids.

Our study aims to answer two questions:

1. How do the effects of the three main alkaloids compare with one another and with an artificial alkaloid mixture of all the drug's alkaloids in a concentration ratio corresponding to their natural occurrence?


2. Can psychodysleptic phenomena be produced in humans through a careful increase in dose, which can be compared with the effects of Psilocybin?


[FIGURE: Fig. 1 — Chemical structure diagrams of five alkaloids found in ololiuhqui with their percentage compositions: D-Lysergic acid amide 45%, D-Isolysergic acid amide 25%, Elymoclavine 5%, D-Lysergol 5%, Chanoclavine 10%]

Fig. 1. The alkaloids contained in ololiuhqui with indication of the percentage share according to Fanchamps (not shown: Ergobasine 10%)


2. Methods

We used the method developed by Heimann (1961) for the study of psychopharmaceuticals in healthy test subjects, which allows precise recording of the induced changes on three levels of psychological life, namely on the level of expression and behavior, of experience, and of psychological performance. The method allows for a subsequent reconstruction of the experimental procedure and a comparison of temporally corresponding findings:

The test subjects (ten physicians who volunteered) are situated with the examiner in an artificially lit room. The examiner can operate, via remote control, a sound-film camera and a tape recorder set up in an adjacent room, and in this way record expression and behavior as well as the subjects' experiential reports at fixed time intervals. At the same intervals, the subject must carry out a series of performance tests. The film, tape recording, and test recordings take place before administration of the substance, and at 45, 90, 135, and 180 min after administration. In this way, four cross-sections of changes on the three psychological levels are captured.

The sound films are evaluated descriptively according to expressional-phenomenological criteria established by Heimann,1 with regard to changes in facial expression, posture, and gesture, as well as verbal expression.

From the experiential reports recorded on tape, predetermined symptoms were counted, so that for each substance and for the total alkaloids a symptom distribution grouped by category2 could be established.

The following table provides information about the experiments conducted with individual substances and the total alkaloid mixture, and the doses administered (administration was carried out in aqueous solution orally):

Table. Overview of Test Subjects

SubjectAgeWeightDose absolute (mg)Dose/kg BW (mg)
D-Lysergic acid amideE. H.337430.04
S. B.357560.09
D-iso-Lysergic acid amideD. B.305820.03
F. D.347240.06
P. S.277550.07
LysergolL. C.347220.03
H.W.I.297240.06
E. H.337460.08
L. G.307280.11
Total alkaloidsB. S.299820.02
J. H.345430.06
J.P.P.217560.08
E. H.337470.10


After 13 experiments we discontinued the study, because at the higher doses used by us, very unpleasant neurovegetative intoxication symptoms were consistently observed.


3. Results

a) d-Lysergic Acid Amide

Expression and behavior of the test subjects changed as early as 45 min after ingestion of the substance: the subjects appeared to be suffering, their facial expressions deteriorated as if after a serious illness, their movements were markedly slowed. The speaking voice showed a decrease in volume, pitch, melody, dynamics, and tempo. In the subsequent examination cross-sections these changes intensified, so that the subjects ultimately appeared drowsy and apathetic. Subject E.H., who had taken 3 mg (= 0.04 mg per kilogram of body weight), recovered after approximately 3–4 hours; Subject S.B., who took 6 mg (= 0.09 mg per kilogram of body weight), had to go to bed following an injection of an anti-nausea medication and did not recover until the following day. In the self-reports of both subjects, complaints about vegetative symptoms predominated: unpleasant, flu-like feeling of illness, nausea, suddenly shooting nausea reflex with vomiting, which could be controlled with 2 cm³ Cyclicinum hydrochloricum. In addition, sensations of heat, sweating, dizziness, feelings of heaviness, and general fatigue were observed. Subject S.B. (6 mg) awoke in the middle of the night with precordial pain and shortness of breath and simultaneously suffered from intense unmotivated anxiety. Thought disturbances, changes in mood (apart from a marked dysphoria), and significant alterations of consciousness were absent.

b) d-Isolysergic Acid Amide

Expression and behavior of the subjects changed in the first examination cross-section in the direction of a drowsily sunken state, from which they could be easily recalled into an engaged and present posture by being addressed. In the following examination cross-section they showed relaxation and a contented, not lifeless facial expression. In the fourth and fifth examination cross-sections, however, they appeared to be suffering, listless to drowsily dazed. The speaking voice showed, during the second through fifth examination cross-sections, a reduction in dynamics, melody, and pitch, while volume and tempo, after an initial reduction, regained their initial values in the last three examination cross-sections.

The results of the experiential accounts parallel the changes in expression: after a relatively brief phase of drowsiness, all subjects felt relaxed and comfortable, in some cases even somewhat euphoric. They seemed to overestimate their capacity for performance. Noted were paresthesias and individual synesthesias, as well as an overestimation of elapsed time. In the fourth and fifth examination cross-sections they complained of difficulty thinking and a poverty of ideas.

In subject P.S. (5 mg), after 3½ hours there was a sudden onset of severe nausea with a drop in blood pressure, which could be controlled with analeptics and anti-nausea medication after approximately 30 min. Simultaneously, the subject experienced a feeling of total annihilation and fear of death, which subsided after vomiting approximately 60 min later, but did not fully resolve until the course of the night.

c) d-Lysergol

Changes only occurred at a dosage of 8 mg, with a clear slowing visible in expression and behavior. Facial expression appeared flat and speech showed a reduction in the five expressive qualities.

Subjectively, fewer vegetative sensations were observed, but a clear inhibition of initiative was present.

d) Total Alkaloids

At low doses (subject B.S., 2 mg), the film analysis showed a drowsy, listless posture in the first cross-section, but in the second cross-section a euphoric relaxation. The previously restrained facial expression changed into a more extroverted conviviality with inappropriate laughter. In the fourth and fifth examination cross-sections this was most pronounced, and the euphoria did not subside until 5–6 hours after ingestion of the substance. From the self-report:

"After approximately 45 min, vegetative discomforts appeared, above all nausea and retching. After approximately 90 min relaxation occurred and the disturbing physical sensations disappeared. Gradually I felt an increasing sense of not caring and euphoria, as well as a pleasant fatigue. At the same time a feeling of heaviness in the head and extremities appeared, which was not experienced as unpleasant. A reduction in critical thinking occurred and a positive acceptance of general passivity. On the whole I had the feeling of a mild intoxication, but compared with alcohol, more euphoria. The sobriety of the surroundings had a disturbing effect.

Approximately 4 hours after the start of the experiment I returned home, where my wife spontaneously declared me tipsy. This mild state of intoxication with clear ataxia lasted approximately 2 more hours and subsided without any hangover feeling. The following night I slept well.

Throughout the entire experiment I was unable to observe any changes in visual experience and also no sensory illusions in other sensory domains."

At higher doses, the unpleasant vegetative discomforts predominated. The experiment with 7 mg (= 0.097 mg per kilogram of body weight) took a rather dramatically toxic course: at the first examination cross-section after 45 min the subject already appeared markedly affected, exhausted, and depressed. Facial expression and gestures were considerably slowed. In the following examination cross-sections the slowing increased and facial expression and speech became flatter. All expressive qualities of speech were diminished, particularly dynamics and tempo. A blurring of articulation also occurred. The subject appeared apathetic and mildly clouded in consciousness. When addressed, the subject responded with a marked delay. During performance tests, sighing breathing was observed. Left to their own devices, the subject immediately sank back into the consciousness-clouded state.

3 hours and 40 minutes after the start of the experiment, a sudden vegetative shift occurred. Within a few minutes the subject became hyperalert and simultaneously showed a pronounced anxious tension. The previously unchanged blood pressure rose to 150/100, the pulse from 72 to 100. Strong pulsations of the abdominal aorta were remarkably visible through the clothing. Breathing became shallow, its frequency fell. The subject expressed fear of death, the facial expression became increasingly pale and deteriorated. A strong mydriasis was noted. Respiratory and circulatory conditions were not, however, dangerously altered; the subject was awake and responsive. This made the subjective expectations of death all the more starkly contrasting. 4 hours after ingestion of the substance, the subject received 4 cm³ Promazine, after which the subject calmed down and fell asleep. Elevated blood pressure and pulse returned to normal values within 1 hour. ½ hour after the Promazine injection, violent projectile vomiting occurred from sleep. 7 hours after the start of the experiment the subject could gradually be awakened and brought home in a drowsy state.

Self-Report of This Experiment

"Already approximately 30 min after ingestion of the substance, some apathy and general heaviness. Conversation with the experimenter already impaired due to increasing inhibition of drive. No vegetative discomforts. After 1 hour, completely drive-less staring into space. Disinterested in all conversation, entire body paralyzed by an unpleasant nonspecific fatigue. After 1½ hours no signs of nausea whatsoever. Instead, an unbearable leaden feeling of heaviness throughout the entire body, particularly intense as a pulling pain in the neck. Slightly ataxic gait. Great indifference toward the surroundings and the experimental situation. A conversation outside the experimental room is fully registered as a sequence of words and melody, but the content of the conversation goes unheeded. Individual words stimulate visual images. Clear, organized thinking is increasingly impaired. Later the test tasks become almost impossible to solve. Speaking and other tasks can only be accomplished after laborious self-collection. As soon as no one is engaging with me, I sink into apathy. At times I find myself in a half-sleep. I have the feeling that time has slowed down. After approximately 3 hours I must lie down, as I can no longer endure the tormenting feeling of heaviness in my body. At this point strange synesthesias occur, in which bodily posture is translated into visual images. A bent arm appears, for example, as an angled, bordered hollow arrow, which is optically hallucinated. Approximately 3½ hours after the start of the experiment I have an indescribable feeling of wretchedness and weakness, without nausea. Breathing is labored. I feel dried out and fear fainting. Suddenly I am wide awake, present, perceiving the personal and external situation very precisely, but deeply worried about my physical state. I fear that the poisoning by the substance is becoming uncontrollable. The experimenter's account of a similar experience in an LSD experiment reassures me for only a brief time. I have the feeling of increasingly deteriorating, and believe I can maintain the shallowing breathing only through iron will. My pulse is hammering throughout my body, especially in my head, which is barely tolerable. Suddenly I am convinced that I must die, whereby thoughts of my family recede entirely behind the vital anxieties about my momentary condition. I try to resist the Promazine injection, because I fear that willful control over the shallowing breathing will be completely lost. After the injection, the severe anxiety gradually subsides as I simultaneously doze off. I experience the unexpected vomiting as a relief. After waking and during the following 12 hours, light physical exertion (climbing stairs, sitting up in bed) immediately brings on the pulse hammering with corresponding anxiety. Only 48 hours after the start of the experiment have I fully recovered."

The two experiments with 3 and 6 mg, resp. 0.055 mg per kilogram and 0.080 mg per kilogram of body weight, lay in terms of expression and behavior between the two described experiments of subjects B.S. and E.H.

e) Symptom Distribution

In the following Fig. 2, the symptom groups are plotted graphically according to the stated frequency for the partial substances and the total alkaloids. We have added together the individual statements from each examination cross-section, on the assumption that questioning in the temporally corresponding examination cross-sections was comparable, and that a symptom reported four times, for example, carries more weight than if it occurred only once. In doing so, because of the unequal number of subjects observed per experiment, the values were each recalculated to one subject.

When comparing the individual alkaloids, it is immediately apparent that d-lysergic acid amide produces the most vegetative sensations, and that the other symptom groups recede markedly with this substance. With d-iso-lysergic acid amide, vegetative sensations are less frequent; instead, stronger disturbances of thinking, affect, and consciousness appear here. Lysergol shows the least subjective changes. When comparing the enumerated symptoms of the total alkaloid effect with those of the individual alkaloids, it is notable that the total alkaloids in their subjective effects represent a combination of the individual alkaloids, and that no new qualitative effects are therefore to be expected from the three alkaloids not individually tested (elymoclavine, chanoclavine, ergobasine) or from the combined application of the alkaloids tested by us.



[FIGURE: Fig. 2 — Four bar charts showing symptom distribution for Lysergic acid amide, Iso-Lysergic acid amide, Lysergol, and ololiuhqui (Total alkaloids), each with categories A through H on the x-axis]

Fig. 2. A Vegetative sensations; B Motor function; C Perceptual disturbances; D Sense of touch, deep sensation; Body schema; E Spatial-temporal experience; F Thinking; G Affect; H Consciousness


f) Performance Tests

In Fig. 3, the mean values of the individual examination cross-sections for the five performance tests used by us are plotted. They are set in relation to a group of subjects who received Psilocybin (N = 24) under the same experimental conditions, and a placebo group (N = 100), so that a statistical comparison between the ololiuhqui subjects (all results of the partial substances and the total alkaloids combined) with Psilocybin and placebo is made possible. The statistical analysis was carried out for the concentration test using Meili's t-test, and for the other tests using non-parametric methods (Mann and Whitney test).

Meili Test. The placebo subjects show a practice gain in all examination cross-sections. The greatest differences appear in the first examination cross-section, 45 min after ingestion of the substance. Here the ololiuhqui subjects show a practice gain not significantly different from the placebo group, while the Psilocybin group shows the strongest impairment of concentration, specifically a slowing that is significant compared with both of the other groups. In the second examination cross-section and in the subsequent ones — i.e., with increasing intoxication — the ololiuhqui subjects fall behind the placebo group and increasingly resemble the values of the Psilocybin group (in the 3rd hour no longer significantly different from them). The comparison of the Psilocybin effect and the ololiuhqui effect with the behavior of the placebo subjects thus shows that the maximum of concentration impairment for Psilocybin lies in the first, and that for ololiuhqui in the last examination cross-section.



[FIGURE: Fig. 3 — Line graphs showing performance test results across examination cross-sections for five tests: Meili Test, Rey Test, Word enumeration with specific initial letters, Forward digit span, and Backward digit span, comparing Psilocybin and ololiuhqui groups against placebo]

Fig. 3. Effect of Psilocybin and ololiuhqui. — — — without medication; —— Psilocybin; — · — ololiuhqui



Visual-Motor Concentration Test according to Rey. The ololiuhqui subjects differ here in all examination cross-sections not only from the placebo group, but are also significantly less impaired than the Psilocybin group.

Word Enumeration with Specific Initial Letters during 30 min. In this test as well, the results of the ololiuhqui group lie between those of the placebo and the Psilocybin subjects. The latter show a stronger impairment of this performance in all four examination cross-sections under substance effect. The ololiuhqui subjects improve their performance in the last two examination cross-sections despite increasing intoxication, so that the results taken together, compared with those of the Psilocybin group, are significantly better. Under ololiuhqui, word availability is similarly, though less markedly, disturbed throughout the entire observation period than under Psilocybin.

Forward Digit Span. Apart from a mildly significant reduction in the third examination cross-section of the ololiuhqui subjects, we find neither with Psilocybin nor under ololiuhqui a significant impairment of purely mnestic performance.

Backward Digit Span. Here we found significantly lower performance in all examination cross-sections for the ololiuhqui subjects compared with the placebo group (weakly confirmed in the first three examination cross-sections, strongly confirmed in the last).

In summary, it can be stated regarding the results of the performance tests that predominantly concentrative performance and word availability are disturbed by both substances, but in different ways.

Discussion

The comparison of the effects of the partial alkaloids and their combinations shows strikingly few differences. In all cases we obtained mild to moderately severe intoxication states, which at higher doses persisted beyond the three-hour observation period and are characterized by a predominance of unpleasant vegetative sensations. These made the experiments extremely distressing for the subjects as a rule and led us to limit the study to a relatively small number of experiments.3

The analysis of expressive phenomena and behavior shows primarily these progressive changes in wellbeing: mood shifts mostly in the direction of dysphoria, at low doses occasionally of euphoria, and reduction of vigilance. At higher doses, slowing of motor behavior, expressive movements and speech, and drowsy apathy are observed. These and a delay in readiness to react indicate that clouding of consciousness is primarily present. Differentiation between the effects of the individual alkaloids was, given the small number of experiments, only possible on the level of experience with the help of a symptom distribution. Here d-lysergic acid amide showed fewer vegetative but stronger changes in thinking, affect, and consciousness. The symptom distribution of the total alkaloids indicates that a combination of the tested individual alkaloids is present here, and that the untested alkaloids or the combination of the alkaloids tested by us produce no new qualitative effects.

Our first question can therefore be answered by saying that the alkaloids tested by us and the total alkaloid mixture differ only insignificantly from one another in their effects.

In contrast to Psilocybin (Heimann, 1961, 1965), we find under ololiuhqui no qualitative modification with phase-by-phase progression. Rather, there exists a progressive intoxication, which is demonstrable both in expression and behavior and in an impairment of concentrative performance. Here there exists a parallelism between psychological performance impairment and the objectively detectable changes in expression and behavior, in contrast to the phase shift of the two observed criteria under Psilocybin (maximum impairment of concentration ability in the first examination section, where expression and behavior are only slightly impaired; maximum of expressive changes in the third examination section, where the results in the concentration tests are already approaching baseline values). As we have set out elsewhere, the progression of effects of model psychoses in the narrower sense4 thus shows a qualitative modification dependent on the duration of the drug's action, which can however only be demonstrated using a research methodology that takes temporal relationships into account (Heimann, 1961).

ololiuhqui differs fundamentally from the previously known phantastica also in that only very few perceptual disturbances occurred; in particular, optical hallucinations were almost entirely absent. The other reported symptoms as well, e.g., changes in time experience, body schema, loosening and impoverishment as well as slowing of the flow of thought, and the mood changes, are relatively discreet — in any case by no means as pronounced as with LSD 25 or Psilocybin. They belong in the category of what one can observe with mild somnolence and nonspecific intoxication. Our results agree with the findings of the studies by Isbell and Gorodetzky, who were able to observe only clouding of consciousness without hallucinations using extracts from ololiuhqui seeds and a synthetic alkaloid mixture of ololiuhqui alkaloids.

When we ask which other substances produce similar intoxications to those caused by the ololiuhqui alkaloids tested by us, we can highlight a certain similarity with the scopolamine effect, which likewise exhibits psychomotor slowing, mild clouding of consciousness, and hypnagogic phenomena (Heimann, 1952). Furthermore, studies with the alkaloid ibogalin (active ingredient from the Apocynaceae Tabernanthe iboga) using the same research methodology have yielded an intoxication state comparable to ololiuhqui without significant productive symptomatology and with mild sedation (Schmid, 1967).

The question arises whether the alkaloids of ololiuhqui are present in the seeds and in the drug itself perhaps in a different form, so that the effect of the total drug might differ from the alkaloids tested by us. Supporting this hypothesis is the recent isolation by Hofmann of a substance closer to LSD 25: d-lysergic acid hydroxy-ethylamide (Cerletti and Hofmann). In his view, it is split through the extraction processes in alkaline medium into the lysergic acid amide tested by us and acetaldehyde.5 Against this, however, is the fact that the effect which Reko described among the indigenous peoples, and the observations by Osmond with chewed seeds of Rivea corymbosa, fit quite well with the phenomena observed by us. Our experiments with d-lysergic acid amide also confirm the results which Solms had obtained with this substance, namely a predominantly sedating intoxication.

When the descriptions by Spanish authors of demonic apparitions under the effect of ololiuhqui are discussed, this need not necessarily involve hallucinations similar to those of the Psilocybin effect; rather, cultural and racial factors could be responsible. Visions in the context of cultic activities, even under the effect of drugs, i.e. through a pharmaceutically reduced vigilance, can be psychogenic. It is therefore plausible to attribute the differences in effect between the laboratory experiment and the descriptions in historical sources to these nonspecific factors. Additionally, there is the possibility that the indigenous peoples possess a greater tolerance for vegetative disturbances, so that these recede in experience.

References

Cerletti, A., and A. Hofmann: Personal communication.

Fanchamps, A.: La psychopharmacologie moderne et les drogues magiques mexicaines. Rev. méd. Suisse rom. 82, 15–31 (1962).

Heimann, H.: Die Scopolaminwirkung. Basel-New York: Karger 1952.

— Ausdrucksphänomenologie der Modellpsychosen (Psilocybin). Psychiat. et Neurol. (Basel) 141, 69–100 (1961).

— Die Wirkung von ololiuhqui im Unterschied zu Psilocybin. Neuropsychopharmacology, 4, (ed. D. Bente and P. B. Bradley). Amsterdam-London-New York: Elsevier Publishing Co. 1965.

—, and G. Lukács: Experimentell-psychol. Differenzierung der Wirkung von zwei Psychostimulantien am Menschen. Psychopharmacologia (Berl.) 8, 79 (1965).

Hofmann, A., and A. Cerletti: Die Wirkstoffe der dritten aztekischen Zauberdroge. Dtsch. med. Wschr. 86, 885 (1961).

Isbell, H., and C. W. Gorodetzky: Effect of alkaloids of ololiuhqui in man. Psychopharmacologia (Berl.) 8, 331–339 (1966).

Osmond, H.: ololiuhqui: The ancient Aztec narcotic. J. ment. Sci. 101, 526 (1955).

Reko, V.: Magische Gifte. Stuttgart: Enke 1949.

Schmid, B.: Die psychische Wirkung von Ibogalin-Hydrochlorid. Arzneimittel-Forsch. (Drug Res.) 17, 485 (1967).

Schulthes, R. E.: A contribution to our knowledge of Rivea corymbosa. The narcotic ololiuhqui of the Aztecs. Botanical Museums of Harvard University, Cambridge (Mass.) 1941.

Solms, H.: Chemische Struktur und Psychose bei Lysergsäurederivaten. Praxis 45, 746 (1956).



Prof. Dr. H. Heimann

Clinique Psychiatrique Universitaire

Hôpital de Cery

CH-1008 Prilly, Lausanne

Edgar Heim

Psychiatric University Polyclinic

CH-3000 Bern, Hügelweg 2



1: Since the conclusion of this study, we have also developed a quantitative method for the analysis of mimic movements (cf. Heimann and Lukács).

2: The compilation can be requested from the authors.

3: On this occasion we would like to once again extend our heartfelt thanks to all colleagues for their willingness and participation.

4: e.g. Psilocybin.

5: In a currently ongoing study we are testing the effect of d-lysergic acid hydroxyethylamide in a chemically stable form.
Solms, Hugo. Relationships between chemical structure and psychoses with the use of psychotoxic substances. 1956. Journal of Clinical and Experimental Psychopathology, vol. 17, page 429

Relationships between chemical structure and psychoses with the use of psychotoxic substances

“Comparative Pharmacopsychiatric Analysis:” A New Research Method*

Hugo Solms, M.D.

Bern, Switzerland


The study of artificial psychoses involves several problems, namely, the question of psychopathologic characteristics or symptomatology, the somatic basis of these psychoses, the difference between inducing and inhibiting chemical compounds, the eventual specificity of psychotoxic effects, the question of relationship of experimental to schizophrenic psychoses, and the like.

Today it is generally admitted that psychotoxic substances do not provoke specific symptoms whether these substances are of a metabolic or pharmacologic nature. All psychotoxic phenomena can be subsumed under the few "acute exogenous reaction types" of Bonhoeffer. According to this author the other existing symptomatologic differences are largely explained by the psychodynamics of the individual, his personal history, his social milieu, and the experimental situation. Nevertheless there are symptomatologic differences that are not sufficiently explained by these factors and therefore other reasons could be involved.

Recently comparative studies of symptomatic psychoses were performed with three halfsynthetic ergot derivatives. These compounds are the well-known lysergic acid diethylamide (LSD) and two others with similar chemical structures. It was shown that the psychotic symptoms produced by these substances, even if chemically similar, gave interesting differences. These differences could not be explained by the psychic constitution of the subject, his life history, his psychodynamics, or the experimental situation.

The question arose, therefore, as to whether there existed an eventual relationship between the chemical structure of the psychotropic compounds on the one hand and certain symptomatologic characteristics produced by them on the other.

In the following study, the psychologic effect of LSD was compared with that of lysergic acid monoethylamide (LAE) and lysergic acid amide (LA). We will not concern ourselves here with the individual content of symptoms but only with their formal appearance, that is, the kind and intensity of alterations in perception, consciousness, thinking, mood, etc.

From structural formulas of the three pharmacologic substances, it can be seen (p. 430) that the side chains in each differ. LSD has two ethyl groups on its amide group, whereas LAE has only one ethyl group and LA is not substituted at all.

It is beyond the scope of this paper to describe the order of experiments on all subjects in detail. Fourteen persons, mainly medical men and chemists, were given LAE and LA respectively under exactly the same conditions in progressively large doses, and a graded series of 32 psychotic reactions were obtained. It will be shown that the formal aspect of the LAE response is slightly different from that obtained from administration of LA. When LAE was given, the different subjects showed a characteristic psychosis in a rather uniform manner that was striking. With the use of LA, which provokes a slightly different syndrome, the response was also rather uniform. Therefore, and because of considerations of the well-known difficulties of the subjects in repeated experimental psychoses, it was deemed unwarranted to continue administration of LSD on the same persons. The author then compared the results obtained using LAE and LA with the well-analyzed experiments of Stoll and Weyl in which LSD was used. Obviously such a comparison must be done with the greatest prudence, but, since the formal aspects of the responses obtained in the group receiving LSD were also rather uniform, it was deemed somewhat justifiable to compare these data while bearing in mind the aforementioned restrictions. Even then the greatest caution had to be used not to overestimate the results.

1. As is generally well known, the symptomatology of the LSD reaction produced with 25 to 100 gamma given orally or intravenously shows as the most impressive symptom many disturbances in visual perception. (Stoll and Weyl recorded that 56 to 78 per cent with LSD-induced psychoses showed these phenomena.) Much more rare are the perceptual alterations of gustation, audition, and touch. Bodily sensations and changes in body image are seen in almost all subjects. Slight disturbances also occur in thinking as do distortions in the perception of time. Consciousness becomes slightly dreamlike and often leads to certain drowsiness. Self-observation and insight remain intact. Important personality disturbances also occur, namely, feelings of depersonalization and experiences of split personality. There are affective alterations and changes in drive. The subjects often exhibit euphoria, which can change to depression. Furthermore, alterations of the autonomic nervous system appear, especially before the onset of the psychotic phase.

With low doses of LSD the neurovegetative disturbances are paramount; on the other hand, with higher doses hallucinations and the whole psychodynamic personality change predominate. The symptoms begin about one-half hour after administration of the drug and remain intense for a mean of 4 hours. The average total experience lasts 8 hours.

2. The effective dose of LAE is about 10 times as great as that of LSD, showing that it is more difficult to create optical illusions and hallucinations with LAE than with LSD, even if one considers the big difference between the efficient or working amount of both drugs.

Small doses of LAE produce the same neurovegetative disturbances as do equally small doses of LSD. If LAE is given in a middle range dosage (about 0.5 mg. per injection), it is not the disturbance in visual perception that dominates during the wavelike (up and down) variations in the psychotic symptomatology but rather (in 64 per cent) the phases of extreme abulia, apathy, indifference, and absence of thought ("Gedankenleere") with feelings of changed personality, difficulties of contact with the surroundings but rather normal responsiveness, and slight drowsiness, which is stronger than with use of LSD. Sleep however does not occur. Disturbances in visual perception were seen in only 33 per cent; in principle they corresponded to those of LSD but did not seem so intensive or impressive.

One of the subjects described the lethargic phase as follows: "A state of absolute euphoria, of well-being; everything seems to dissolve in the distance, everything becomes unimportant, there is great indifference and difficulty to think and to remember the past. Will power fades away and doesn't react as usual. . . ." Other subjects perceived this state of being overwhelmed and the inability to resist as disagreeable and pressing.

With increasing doses of LAE (about 0.75 to 1.00 mg. and more per injection) the lethargic-apathetic syndrome occurs more often and more intensively (in 83 per cent). The same pertains to the decrease of consciousness and to the optical hallucinations (in 66.5 per cent). Occasionally the latter symptoms can even dominate the picture for a certain time, so that the same phenomena is obtained as with LSD, particularly hallucinations.

This type of high dosage LAE response, identical to the LSD syndrome, was described by a subject as a succession of "images;" such as many friendly lion heads, birds with white feathers, many men with top hats, spider webs, warriors with trumpets, many pelicans, and many peacock feathers. Everything occurred quickly, changed continuously, and had no connection. At the same time the subject noticed everything that happened around him, especially acoustically. It was as though he existed simultaneously in two worlds, one real and the other a dream. He was fascinated by the experience but was slightly indifferent to reality. The symptoms occurred in succeedingly intensive phases. At the same time a tremor in the masticatory muscles was experienced.

There are, then, no principal differences in the mental symptomatology produced by LSD and LAE. Both drugs can bring about the same symptoms, but in general one can say that LAE produces lethargy, indifference, drowsiness, apathy, and abulia more often than does LSD. The deterioration of consciousness is slightly greater with the use of LAE. Finally, the hallucinatory phenomena, which are exceptional with small doses of LAE, become frequent, intensive, and impressive (as always with LSD) with high amounts of LAE.

3. The effective doses of LA are the same as for LAE, but LA induces greater indifference, a decrease in psychomotor activity, and a desire to sleep much more strongly than does LAE, until finally an increased clouding of consciousness produces sleep. LA may provoke sleep after one-half to one hour; if the subject is not awakened, sleep lasts approximately two hours. If the dose of LA is increased, no certain hallucinatory experiences can be noticed, but uncomfortable autonomic disturbances do occur, such as, hypersalivation, emesis, dizziness and diarrhea; sometimes irritative depressive moods occur concomitantly. Because of these symptoms the tolerance point was considered reached.

With middle to strong doses in 1 subject work became increasingly difficult after 30 minutes. After forty minutes he began yawning and experienced a sensation of inability to use the limbs, a feeling of sinking into nothing, impaired concentration, and an immediate desire to sleep, after which he slept for three hours during the day.

Using the greatest prudence the following provisory interpretations are proposed. If ethyl groups are substituted on the amide group of LA, its power to produce hallucinations seems to increase. On the contrary, if the number of substituted ethyl groups are decreased, hallucinatory potentials are also weakened; i.e., the visual system seems less affected, but psychomotor activity decreases and clouding of consciousness is augmented until sleep occurs.

Of course it remains unsettled as to whether the observed differences in the psychopathologic and psychotoxic effects of LSD, LAE, and LA depend directly on the structural differences of the side chains of the three drugs. This cannot easily be determined. It is not even known how the psychotropic lysergic acid derivatives become effective in the human organism and where they actually function. One is forced to question whether the psychotoxic substance becomes effective through its total structure, or if the psychosis is caused by a result of its breakdown or through the influence of intermediary metabolites. Another possibility is whether the various psychologic responses to these three compounds depend on the differences in the resorptive, metabolic, and excretory processes of the drugs. Or perhaps a chronologic factor may be involved, that is, one substance may metabolize faster than the other, thereby causing psychopathologic differences. There is also some question as to whether these three drugs attack different hypothetical receptors, such as in the brain. Today we have almost no knowledge about the relationship between chemical structure and psychotic symptomatology of psychotoxic compounds. Why, for example, do the hallucinations dominate in 1 case and a clouding of consciousness dominate in the other? What, for instance, are the somatic conditions for the appearance of hallucinations in symptomatic psychoses?

This paper introduces a new procedure to deal with these questions, which we call comparative pharmacopsychiatric analysis. By this is understood pharmacopsychiatric research, wherein one works not only with one specifically defined psychotoxic drug but also with additional compounds that are only slightly modified and therefore remain closely related.


SUMMARY

The psychotic reactions produced by three chemically related lysergic acid derivatives show similarities and differences. Their comparison gives some insight into the problems of the relationships between the chemical structure and the psychotic symptomatology with the use of psychotropic drugs and may facilitate understanding of the somatic foundation of symptomatic psychoses.

Since this research method employs a series of slightly modified psychotoxic substances the name comparative pharmacopsychiatric analysis is suggested. This procedure is proposed as a new adjunct for study in experimental psychiatry.


ACKNOWLEDGMENT

We are indebted to Prof. E. Rothlin, former Director of the Pharmacological Laboratories of the Sandoz Chemical Co., Basel, Switzerland, for providing lysergic acid derivatives.


RESUMEN

La psicosis artificial producida por tres derivados del ácido lisérgico químicamente relacionados, mostró similitudes y diferencias que ayudaron a explicar la relación entre la estructura química y la sintomatología psicótica. Este método de investigación puede constituir una ayuda para mejor entender los fundamentos somáticos de la psicosis sintomática.


RESUME

La comparaison de la symptomatologie des psychoses provoquées par trois dérivés psychotoxiques de l'acide lysergique, apparentés chimiquement, permet de discuter certains rapports entre la structure chimique de la substance psychotrope et l'altération psychotique produite par elle. Et l'auteur propose d'utiliser des substances psychotropes possédant une structure chimique étroitement apparentée pour faciliter l'étude des rapports entre les modifications pathophysiologiques et psychotiques, dans le domaine des psychoses toxiques. Ce nouveau procédé est appelé "analyse pharmacopsychiatrique comparative."


*From the psychiatric clinic of the University of Basel and the University of Bern, Switzerland.


BIBLIOGRAPHY

1. Abramson, H. A.; Jarvik, M. E.; Levine, A.; Kaufman, M. R., and Hirsch, M. W.: J. Psychol. 40: 367, 1955.

2. Arnold, O. H.: Wien Ztschr. Nervenh. 7:188, 1953.

3. Becker, A. M.: Wien Ztschr. Nervenh. 2:402, 1949.

4. Bleuler, M.: Deutsche med. Wchschr. 81:1078, 1956.

5. Bonhoeffer, K.: Die symptomatischen Psychosen. In: Aschaffenburg: Handbuch der Psychiatrie, Deuticke, Wien, 1910.

6. Callieri, B.: Clin. Terap., 1955, pt. 2, p. 174.

7. Cleghorn, R. A.: Am. J. Psychiat. 108:568, 1952.

8. Georgi, F.; Fischer, R., and Weber, R.: Schweiz. med. Wchnchr. 81:817, 1951.

9. Hoch, P. H.: Am. J. Psychiat. 111:787, 1955.

10. Hoch, P. H.; Cattell, J. P., and Pennes, H. H.: Am. J. Psychiat. 108:585, 1952.

11. Hoch, P. H.; Cattell, J. P., and Pennes, H. H.: Am. J. Psychiat. 108:579, 1952.

12. Hoffer, A., et al.: J. Ment. Sc. 101:12, 1955.

13. Hoffer, A.; Osmond, H., and Smythies, J.: J. Ment. Sc. 100:29, 1954.

14. Lindemann, E., and Clarke, L. D.: Am. J. Psychiat. 108:561, 1952.

15. Mayer-Gross, W.: Brit. M. J. 2:317, 1951.

16. DeShon, H. J.; Rinkel, M., and Solomon, H. C.: Psychiatric Quart. 26:33, 1952.

17. Rinkel, M.; Hyde, R. W.; Solomon, H. C., and Hoagland, H.: Am. J. Psychiat. 111:881, 1955.

18. Savage, C.: Am. J. Psychiat. 108:896, 1952.

19. Schwarz, B. E.; Wakim, K. G.; Bickford, R. G., and Lichtenheld, F. R.: A.M.A. Arch. Neurol. & Psychiat. 75:83, 1956.

20. Solms, H.: Méd. et Hyg. 260:51, 1954.

21. Solms, H.: Schweiz. med. Wchnchr. 83:356, 1953.

22. Solms, H.: Schweiz. Arch. f. Neurol. u. Psychiat., 1954, vol. 73, pt. 1 and 2.

23. Solms, H.: Praxis 32:746, 1956.

24. Stoll, W. A.: Schweiz. Arch. f. Neurol. u. Psychiat., 1947, vol. 60.

25. Tonini, G., and Montanari, C.: Gior. psichiat. e. neuropat., 1955, vol. 83, pt. 2.

26. Walther-Buel, H.: Schweiz. med. Wchnchr. 83:483, 1953.

27. Weyl, B.: Medical dissertation. University of Freiburg, Breisgau, Germany, 1951.

28. Wikler, A.: Am. J. Psychiat. 108:590, 1952.
OK so I have never done this before so after many, many years of rampant substance use and the accompanying self destruction I thought I would give it a go and see if it helps me in any way, even if it is just documenting the actual substance use....perhaps when compared to others it may not actually be that rampant.
I also wonder if it might keep me more accountable, because if there's one thing I excel at, as do most addicts it's self denial and just generally convincing myself that things aren't all that bad.

So I'll start with my age...I am currently 52....born in 1974.

This is how my day went today.

I got out of bed at about 7:30am, feeling pretty seedy as I took to much bromazolam last night.
When I start taking to much bromaze I start to experience the amnesia that benzo's can produce, so I couldn't say exactly how much I took, I think it was either 9mg or 12mg.

Either way I wasn't feeling great, so I grabbed my bottle of methadone, I had a take home for today so that was a bonus.
So down the hatch with 60mg of methadone, I try to be on the lowest dose of methadone that keeps me stable/comfortable but I rarely use other opioids to get over my dose, if I'm on an appropriate dose I mostly feel good as long as I am not playing up with other substances, which is not the case right now.

So my day starts with 60mg of methadone, I have been up and down on my dose over the 26 years I've been on it but 60mg is about where I sit most of the time.

After drinking my dose I get started on the second beverage of the day...my morning coffee.

By the time I've made my morning coffee my dose is kicking in and I'm starting to feel ok.

So to go with my morning coffee I also take a couple of hits on my weed pipe.

This wouldn't be a problem other than the fact that my spiritual beliefs are the number one thing in my life and I made a vow to my God that I would not smoke weed anymore.
In hindsight it was a poor choice to make such a vow because I have absolutely loved my green for nearly 40 years and I just should have known I would not be able to keep that vow without a slip here and there.

As much as I love my herb I cannot smoke it without feelings of guilt and anxiety, which is, of coarse, where the benzo's come in...though to be honest, that surely isn't their only purpose.
By now it's about 9am or so and I have already got 60mg of methadone on board and an nicely toasted thanks to the high grade medicinal weed that is just everywhere these days.

I manage to have some breakfast at around 10am and I potter around the house trying to fill in time until I can drop some bromazolam which I finally do at around 2pm.

My wife arrives home at this point and lets me know a visitor will be popping around shortly with a few points of some meth that is supposed to be very good.

Normally I would pass on this as I am more of a downer man than an upper, however I have been known to indulge, particularly if it is good, which this is supposed to be, and I have plenty of bromazolam, already on board, and more on hand if needed.

Now the list is starting to get a little more interesting...60mg of methadone...some seriously filthy weed and now 3mg of bromazolam, taken about half an hour ago, and it's this which I blame for my decision to have a couple of puffs when the rock arrives.

Ther's no doubt it's good rock, I can feel the tingle start at the back of my head and work it's way down my spine. To make things even better there isn't a hint of anxiety that usually comes with my adventures with the glass pipe.
I'm not sure if this is a good thing or a bad thing but it appears I can have a few sweet puffs if I already have some bromazolam on board, likely this would work with any benzo but bromaz is my current favourite and that's as good a reason I need to use it.

Ok that was my day from getting up around 7am and it is 6:20pm as I type this...I have had a couple more puffs on the sweet puff and I'm sure I will finish the day with another 3mg of bromaz.

That my day on Monday the 15th of June 2026
Just as a side note, I am on testosterone replacement, mirtazapine at 30mg each night and perindoprile 8mg daily
Palimpsest

Des Murs De Mots
Des Mots De Murs
Des Maux De Mots
Des Murs Devots
Au Camaieu Des Mots


By:
Pour Le Art

In het Nederland s

MUREN VAN WOORDEN
WOORDEN VAN MUREN
WOORD PIJNEN
VROME MUREN
IN DE SCHADUW VAN WOORDEN

In English

WALL OF WORD S
WORD S OF WALL S
WORD ACHES
DEVOUT WALL S
IN THE SHADE OF WORDS

Which somewhere in 1992 appeared on walls in Paris,
made by a marginal printer/ word artist, Pour l' Art.
Who only was able to present it illegal to the public,
using only 2-nd grade material to work with. On wall s in Paris.

All the walls are cleaned now.
So the limited edition print of the photo is what remain s.
Of the OG and pictures of other people,
maybe the original material still exist s. Mysterious !

I found it a island further in a thrift shop. For close to zilch.
The photographer who made it:
Adri Verburg/ Paris-Middelburg [Zeeland] .

Who worked with Carrera Pers/ Middelburg.
And is permanent showed in Zierikzee/ Old City Mall Museum
But also in Amsterdam in the 'Old City Mall Museum' and Leiden
The Print Cabinet Museum. Pretty established artist.
Found a reference to Drukwerk in de Marge.

These trails i still have to follow, hence T.B.C.
To Be Continued. It is a disease the need to know.
Getting to the bottom of things, it frees the mind.
Puts the soul on ease.

The reason this 2-nd print of a French form of street art.
Ended in a thrift shop in Goes, which is near Middelburg.
Circle round till now.

It got a double meaning when i started writing,
Walls of Words allover Bluelight.

Derived from a school song, to learn French.
It got a extra meaning when my Walls formed its-self.
Been plastering the whole site with it.
In a daze of insomnia by mental torture through noise.

Brought by a 3-rd renovation round on my rent house.
[attempt 1 & 2 failure s] and Overdue maintenance.
Then clicked on ... [mister Ed, the horse] Blog.
And read the disaster he and his family are going through.
:eek:

But the idea to Blog them instead of Walling my thought s.
That was 💡 i gonna blog my word s. Problem dissolved !

All made sense, the puzzle solved to. Noise the culprit.
Stress, insomnia, seizure, Myalgia [without brown urine]
and totally insane driven by noise torture. Makes sense.

Men i slept on the couch and woke at midnight.
Turned of the lights headed to bed.to be woken by:
renovation activity noise, good-morning rotten world.
To discover i ate Sauerkraut with Tempeh last night.

I have no recollection cooking or eating,
nor falling asleep on the couch. :oops:

So this morning i declared war "metaphorically", to my landlord.
And started constructing a 3 stage Ballistic Missile from words.
Doing a etiquette tomorrow in my street, to find support.
Doing it collective is better, but the people here are scared.
To stick there head above the mowing line.

So it might become a solo thing. All By Myself.

Though i rather have some leverage [Hefboom],
makes a bigger point. But these island dweller s.
Not only they rather fuck their Mother, Father or Brother.
Then a genetic better distant lover.

They are all even bigger faggot s.

As it s UNACCEPTABLE, i will go to the bottom. Through the drain.
As its driving me insane. And change has to be-forced.
You don t wait for it to wash down on you like rain
But then again nothing like Ed and his family are going through.

eMKee

[And use this Blog instead of Bluelight to for-fill my need for,
venting/ sorry to anyone who encountered my wall. Skip em.
It was therapeutic for me, but irrelevant at the end].


We all got a backpack with troubles, mine is full.
If i don t create em myself i got a whole team,
creating em for me. I gonna leash myself.

emkee. 🤫🏋️‍♂️⚖️
Welcome welcome my children. This is THE REAL, VERIFIED @Keif' Richards comin' at you with some more capital "T" Truth bombs (loud explosion sound effects). As the one and only voice of drug users globally, I have a responsibility; that responsibility is to regurgitate the most critical information; my knowledge, my experience, my philosophy; into the open beaks of our society, as does the Adult Emperor Penguin to Baby Emperor Penguin. Come on Penguin, I even included a Penguin reference in the story, how about some of that sweet publishing cash. What say you let yours truly, wet... his beak a little? But the crown weighs heavy, as they say. The constant clamor for more blog posts, more stories... more wisdom... my Gmail overfloweth. Still, this is important work. Continuing on from part 3 - The Mission to Fuck Criss Angel.

"Have you ever been photographed before?"

A short, stout man with an effeminate Southern accent was speaking to me. I had been working odd hours and finding sleep wherever I could. I looked up, rubbing my eyes. The man wore an unbuttoned dress shirt. Around his ample waist, a purple sash. A pink bandana on his head was complimented by a filthy eye patch. I realized only too late, I was on the strip and actively being groomed by a modern day pirate. On his waist was a scimitar, wooden yes, but still a perfect instrument for beating the shit out of someone. The pirate's eyes met mine and in them I saw the wild lust of a man who had been at sea for too long. His confidence; yes, it was clear this man had raped before, and would rape again.

Just then, out of the corner of my eye, I saw two uniformed police officers. I was saved. In that moment, I juked my would-be rapist whilst howling like a little girl for help. The officers turned around and I noticed a wry smile on their faces. "Where do you think you're going handsome?" said one of the cops, apparently having the exact same, weird, effeminate Southern accent of the pirate. "Did 3 gay dudes from New Orleans move up here just to cosplay and rape?" I didn't have time to ponder. My transgressors surrounded me and moved in slowly. I clenched my butthole as hard as I could. Then, I laughed, "isn't this town just whacky?".

I woke up in the office with my head on the keyboard. It was ~4am and my partner @Godjilla was busy with her crochet work. We had to start getting ready to wake people up. You have to make coffee, set out the free food if we have any, clean the tables off and make sure the laundry is straight for the day, among other record keeping. The place was only half-full. The absence of a large portion of our normal census provoked immediate dread and anxiety. Weird shit had been happening among not just us, but other non-profit operations of a similar nature.

For the record, this is all fiction, I'm not at all implying that any of what I'm writing is real or really happened, so there.

This story will continue momentarily, stay tuned.
i thought i would start blogging on here assuming this is the blog page idk my brain is too fucked to understand forums with blogs im just used to forums with just forums
today is 05/06/2026 i believe ? yeah probably that. today i took 75 milligrams of diphenhydramine to kickstart the day, ive started using one pill less so instead of 4 dph in the morning i now take 3 because 4 would always start out euphoric then more euphoric then knock me out for an hour (usually in my morning free period) then id wake up and have a mild euphoria and sedation for the rest of the day
im thinking about quitting dph as it will fuck up my brain so i might switch to dxm or propylhexedrine as my daily drug
side note yes the dates are fucked up I started writing this yesterday then the dph I took knocked me out
hopefully I will make more art today as I just got my shipment of benzedrex
that will be all for this post
have fun people
Hello my fellow miscreants,

I hope everyone is enjoying President's Day. Call me crazy, but I just feel infused with the spirit of the holiday season. President's Day was always a massively important holiday in my household. Tradition would hold that my Father would get coked up, have a few rum n' cokes, start fighting with my Mother (Why do I never get to go Scuba Diving?!?!?!) and my brother and I would play Mario Kart for a few hours. The fondest of memories. My Father would inevitably end up yelling about Bill Clinton. As a very young child, I appreciated the trust my parents gave me. They trusted me enough for me to learn what "jizz" meant several years prior to what one would consider an acceptable age. What a truly lucky boy, I thought. I didn't know much at that time, but I knew, one day, I too would jizz all over someone's nice dress and through the grace of God, I've jizzed not only on dresses, but indeed sweaters, socks, human hair, hamster hair and on days when my aim was true, into my own mouth as a parlor trick.

Anyway, what is my life like these days? Well, I'm a fool and always will be. I was put on this earth to make an ass out of myself for the humor and derision of my peers; perhaps to provide them with feelings of safety, security or esteem. "At least I'm not as fucking stupid as that guy, maybe there is hope... you know what, I'm getting off this bridge and going home to my family". Just when you think you have no purpose guys, you're totally useless, don't ever forget, your failure and misery can be catalysts for the happiness and success of others, so don't give up y'all. As the venerable Pamela Bondi would say "The Dow is at 50,000!" Does this mean anything to me? No, however, I'm sure it must be a very good thing.

I was due to start working a new job in Vermont. I fucking hate Vermont, okay? It is ridiculously expensive. It has no reason to be so expensive. It is like my home state, Massachusetts, except without any of the good stuff. Bad schools, high taxes, insane rent and a government that has completely fucked up the economy of the state, irreparably. The quality of life has reached a point of becoming completely untenable. I had just left a relationship that, as time passes, I realize just how totally fucked up it was. The state is full of hypocrites. They want all of the black and brown people to have everything and anything they need, just as long as they don't have to look at them or see them. They want the addicts to be taken care of, but they don't want to have to step over them on the street as it is just unsightly. People who refuse to eat animals, but can watch football players be made into mental retards for sport, running headlong into each other, rendering their brains into applesauce by the time they retire. People who say they they don't need luxury, but spend hundreds of dollars on useless shit, like a 400-500 dollar mask with lights on it that is supposed to make you younger. Then they argue about money. Hypocrites.

I got a job offer in my email. Las Vegas, a chance to be a caseworker and outreach worker for a Homeless Services non-profit. They offered me a 3,000 sign-on bonus if I would relocate and work for them. I though, "this is crazy". There was no way I could make a move like that. Then, I thought, it would be crazy to stay here. What does this state do for me, nothing. I contribute to the tax base and the liberal government spends the money as if they have not a single brain cells nor any personal experience. We put up homeless people in hotels, indefinitely, requiring nothing from them in return, no work, no volunteering, no programming. Look, you know I'm as liberal as they come, but there is nothing for free in this world. Help is just that, help. We, as human beings are required to help our fellows when able. We cannot, however, support people indefinitely with literally zero positive outlook. It doesn't matter how big your heart is, the reality is, nothing is free and help is meant to help people onto their feet. I don't care if that takes years, even fucking decades, as long as you are working toward a tangible goal.

A studio apartment in Burlington is ~1500 at least. In the Vegas metro, I'm able to get a shitty studio for 750. I am getting a one bedroom near the strip for 1200 with everything included once I get my money together. I'm working for this organization. I've been and done my paperwork, I have my identification and everything is a go. I've now worked two shifts and I must say, I'm really liking it out here thus far. It is too early to tell if I really will be comfortable here, but I was not comfortable in Vermont. I hated it. It had nothing for me and it was slowly suffocating me under the weight of the cost of living.

I had two weeks to get out here to start the job. I didn't have any money saved. I made the decision that I would use the money I had to buy a bus ticket halfway and then continue hitchhiking from Chicago the rest of the way. I have hitched before and I know the rules. Make sure your hair is combed, you don't smell bad, tell them the type of work that I do and always keep a smile on your face. Do not ever talk about politics. DO NOT EVER TALK ABOUT POLITICS.

So I spent the last of the money I had on the ticket out to Chicago. I've hitched before and I know making it to Chicago is the best way to stage the rest of your trip out west. The fact that it is such a big city and a major transportation hub makes it easy. Even if this was not the most direct route to Vegas, I gambled that it would be easier ultimately. I collected a week of Methadone from my clinic, got as many scripts as I could cobble together and got on that fucking bus. The feeling of leaving Vermont was euphoric. I had never liked it. I had never intended on staying longer than a year or two. I had always known I'd go back to Boston. I didn't. I was never able to get past living paycheck to paycheck. The breakup I went through caused me to blow through all of the money that I had trying to live. I was leaving all of that behind. All of the bullshit, all of the confusion, all of the false-love that I had felt. I knew, I was taking a risk, but I had to. I was done sitting and waiting for life to happen.

I made it to Chicago. I left with 50 dollars in my pocket which I intended to use for food. I hitched with a family who was traveling to the Grand Canyon. This was a blessing. They actually fed me, talked to me and were just generally very friendly. We were in the car together for about 10 hours. They had 3 kids with them. I paid my way by keeping the little ones occupied and smiling. It was the husband, wife, then me and the three kids in the back. I was telling them stories and jokes and just trying to make them laugh. I feel like the parents were ultimately thankful for my babysitting the kids. I've worked with kids my whole life and I frankly enjoy little kids (in appropriate doses), so this encounter was nice. I ended up breaking away from them in North Texas, right around Lubbock. They didn't ask for any money, though I offered. They even gave me a sandwich and a coke to take with me. Don't ever forget there are nice people out there in this cruel world guys.

North Texas to Vegas was undoubtedly the shittiest part of this journey. I ended up spending 24 hours at a truck stop in Tucumcari, NM waiting for a ride to take me further west. This town is NOTHING. It is about 2,000 people and it was the hub city for everywhere within 2-3 hours. I rode with one trucker. We ended up at odds as he was listening to the radio and we ended up talking about ICE and I couldn't keep my mouth shut. Most truckers are quite conservative. I knew this, but chose to open my mouth. This should have been a straight shot, but I got kicked out halfway to Gallup. Luckily, I immediately found another trucker who got me to Gallup. I again ended up stranded in Gallup for 48 hours. I was starting to think I was never gonna fucking get out. Now, by the time I got to Gallup, I had been on the road for a total of 8 days, so I was out of Methadone. I was starting to get sick and there weren't a lot of places to stay there.

I ended up going to this hotel on Route 66 in Gallup. I did my best to charm the pretty girl who was working the front desk. I believe a more handsome, more charming man could have gotten a room. However, I'm just as God made me; this is a problem. I explained that I was on my way to a job as a social worker in Las Vegas. I spoke a little bit about my political views (everyone working there was either Indian or Latin) and they looked upon me with some pity. They allowed me to sleep in the lobby of their hotel and I was so thankful. They allowed me to use the shower too which was just amazing for me, as I was just dirty as fuck by this point.

I eventually made it out of Gallup. I was able to get a ride to Boulder City. Mind you, I literally had nothing at this point. I literally had zero money. I was entirely reliant upon the kindness of others to get me places. I didn't even have money to take the bus from Boulder City to Vegas. It seemed I was going to then be stuck in Boulder City, with Vegas tantalizingly close. I explained my situation to the people working at a convenience store and the middle-aged lady working the counter said she would give me a ride wherever I needed to go as soon as her shift was over. Man, I felt like I was just getting lucky my whole way through here. The kindness shown to me by these strangers was great in a two-fold way. First, I needed the practical help they provided, but I was also pleased to see they were so willing to offer kindness to this complete stranger. The whole thing, my trip, warmed my heart in this way.

I got to Vegas a couple of days ago. The organization I'm working for operates the largest low-barrier shelter in the vicinity. They have sleeping areas for staff. Part of why I came out here with nothing was because I knew I could rely on them for shelter until I had the bread I needed to get my own place. I have my eye on a one-bedroom close to the strip and close to my work. That is the dream at this point.

I've only worked a couple of shifts, but every indication is that this is the right place for me. My job is to be a support for the homeless community, be it emotional, physical or helping them to connect with the services they need. Also, I will be in charge of a 3 person team and we will be doing outreach near the Strip. This outreach is just a mobile application of the same work I would be doing within the shelter physically. I have always wanted to do street outreach. Like I said, it's too early to judge, but I am getting signals from the universe that this is the right decision. It was absolutely crazy to move somewhere with nothing, but something in my gut told me it was the right thing. I would get the sign-on bonus after a few months and this would enable me to truly start over.

I am currently staying at my work, working full-time and generally, kicking ass all things considered. This was an insane risk. I could've ended up in some seriously sticky situations considering my drug dependencies. I trusted in God and hoped that I would b seen through and I was. I'm currently dead-ass broke until I get my first paycheck. The upside to all of this is that they pay weekly, so I will be starting to generate income in just a little while. I've got enough scripts to get me through until I have money to pay an urgent care. I am only able to get Methadone by going to the ER at this point because I can't yet pay the clinic here and I'm not insured. I'm kind of just doing that every other day, however it really sucks because it's always 4-5 hours at the ER and that means a large part of my free time is consumed by getting Methadone. This was something I knew would happen. I have to wait until I've got some income, then I can start checking these things off.

I made a crazy decision, but everything has worked out thus far, albeit with a small dose of pain. I can't truly complain. I'm here and I have a job. I have to endure life as a bum for a week, then I can start rebuilding. I appreciate everyone who has taken the time to read my little misery-porn-blog. I have every hope of turning this into an optimism-porn-blog. This cosmic, eternal fool, perhaps he can make us all laugh at his stupidity without him having to live in a cold, miserable world of pain? Perhaps I can just be a lovable rogue. I can have friends, optimism and a decent life, even if King John eventually hangs my ass, people will remember me fondly. Until next time guys.

Keif' Richards
───────────────────────
I made a post in this subreddit a while back about how I got drugged by a person who I thought was a friend. Long story short, he put 3 tabs in an edible and had me take it. I ended up having the wildest trip in my life.

People in this subreddit and my gf encouraged me to drop him as a friend as well as my entire friend group since they encouraged it.

Well… I heard through another friend that this idiot did it again, this time to someone I don’t know.
───────────────────────
Read more: h‍ttps://www.reddit.com/r/LSD/comments/1sy03qk/friend_who_put_tabs_in_my_edible_strikes_again/
Hello my fellow miscreants. I´m reporting to you live from Las Vegas, NV. I´ve had the pleasure in my stupid, foolish life to experience some of the most beautiful places in the world. I´ve gotten to walk around Ankor so jammed I was asked to leave. I have been to a Kiss concert in Manchester, NH so jammed that I was asked to leave. I´ve walked the streets of Istanbul, so jammed that I was ¨asked to leave¨. Well, times change and I´m not getting nearly as jammed, nearly as frequently. I´m unable to function as a full-time junkie at my advanced age. I guess I picked a bad time to stop doing Heroin, because now I´m in this shithole. If a city can indeed be ¨alive¨, then that means necessarily that a city can also be ¨dead¨. Las Vegas is a dying city. It is a model that a charicature artist has redone over and over, using the previous charicature as the guide for the next one. Vegas is a bad joke and the punchline is that life is fucking depressing here.

They say that the Luxor is haunted. I had some time to kill before I had to be at work. I don´t have any money to speak of, so I stick out like a sore thumb in these places. They say that Criss Angel lives in the very top of this ridiculous, Egyptian-themed cum 90´s cultural abortion casino. I walked the main atrium. Being that the building is a literal fucking pyramid, they have these special Wonka-vator contraptions that operate diagonally. Do I dare step into the elevator? Surely the Criss Angel penthouse isn´t so easily accessed. Come to think of it, he probably just teleports. Mindfreak. I have many goals in my life right now. I have dreams of getting my driver´s license and getting a shitty car. I also have dreams of having enough liquid income to court Criss Angel´s attention. Lots of random people die/commit suicide in this place. The atrium is practically made for it. I can only imagine that the magic field emitted by Criss Angel´s dark arts have some kind of effect upon the hotel,

I´ve been doing casework at the Rescue Mission herre in the city for a couple of months now. They have been busting up homeless encampments it seems every other day. We are seeing people coming in in waves. We now have people sleeping on every open floor space in the mission. We were not prepared for this influx of people. We ended up with both a bed bug infestation and a ringworm outbreak within the same week. These people cannot be adequately cleaned or quarantined. It´s a fucked up situation.

The law in Clark County is something like: it is illegal to sleep outside in public spaces if there are ANY beds available at ANY shelter in the county. Conservatives I speak with in the course of my work (the fire department, lots of EMT´s, cops of course) think this is a great humanitarian victory. In reality, we do not remotely have the resources to provide safe, hygienic support for these people. The outbreaks of infectious conditions is troubling. It means nobody wants to stay outside. Naturally, people do not tolerate sleeping with bed bugs and god knows what. They leave to sleep outside. I hear the next day from a friend/acquaintance that they were arrested for what amounts to ¨Vagrancy¨ to use an older term. To put this in perspective, there was one guy who was allegedly arrested and he hasn´t been seen for over a month; not at the mission and not been seen by his people on the street.

There are a lo of really fucked up rumors that have gathered steam. One of these rumors is that homeless people are being murdered/abducted with impunity by who the fuck knows. I´m not actually living out there with these folks and I only get to see them briefly at night. However, it is pretty much not questioned by any in the homeless community that people are disappearing. People have stories that are frankly a little chilling. Some say it´s the cops. Some say it´s red-blooded Americans trying to take back their streets as vigilantes. Who knows. At this point, I find it hard to deny based upon the convivtion with which these people believe. People are afraid of the police. I´m not saying they dislike the police, hate the police, resent the police; people are afraid of the police because nobody knows what the fuck is actually happening.

I´ve been staying at the shelter in the office which is quarantined from the rest of the shelter. Alternatively, I stay with my coworker Jill. We have an arrangement that I´m not going to get into, but we are surviving and working together. We do not make a ton of money. I make 25/hr as does she. She is relatively new to Nevada as well and we have joined forces and that has helped me get acclimated to this place. I´m only just now beginning to get comfortable here. We have goals now. It looks like if we combine our resources, we could be in a decent place near our work that isn´t terrible.

I understand we are in tough times right now. I see it everyday with my clientele. Their state gets worse every day. I don´t believe anyone should be wearing clothing infested with bed bugs that is worn until it disintegrates. This is America. I only hope that we are able to come together and find a way to love and understand one another. We have to find a way out of this partisanship and stop fighitng and start working together. The planet is dying and we have literal retarded/satanic-pedophiles running our country. I don´t claim to have the answer. I just know that people need support. I needed plenty of help just to get to the relatively low level of functionality with which I live my life. I´m grateful to God and everyone who has been there for me. It´s for that reason that I have the will in my heart to be there for the peope who are still out there struggling.

I´m making a vested effort to get back into the forums. Plase forgive me fam. I´ve been adjusting to this new place, a new job, new relationhips with new people and it´s all a lot. As I get a little more comfortable and used to the day to day, I have more speace available in my brain. For now, I´m going to try to find an app that can teach me magic the same way Duolingo taught me Spanish. Itt´s unlikely that someone as magical as the Mindfuck himsef would take notice of someone as un-magical as myself. This is my own Harry Potter story, just with more drugs, more nudity and more hookers.

-Keif
If you had told me in 2019 I'd get 7 years with her I'd have taken that offer so fast your head would still be spinning.today at its conclusion. But time I've learned is less a commodity and more a torture device. You can't buy it sell it keep it. It's only appreciated through its loss like as a kid when the screen flashed times up Starfox! You lose.....

Being honest with myself I can even see why this might not be a terrible thing. She is a violent manipulative psychopath and that's just the obvious shit. She's lazy never wrong. Quick to blame me. I truly believe her main goal in life is too make me dope sick. It's yours if I buy the bag and hers if she buys it. She gaslights constantly truly an awful pos human......

But I fucking still love her.ci believed for years that I was the problem. I literally replaced my mom with her....... Damn...... That's fucked up. I just fucking a
Separation of four isomers of lysergic acid α-hydroxyethylamide by liquid chromatography and their spectroscopic identification. Flieger, M., Sedmera, P., Vokoun, J., R̆ic̄icovā, A., R̆ehác̆ek, Z. 1982. Journal of Chromatography A, 236(2), 441–452. 10.1016/S0021-9673(00)84895-5

**SUMMARY**

A method is described for the separation of four isomers of lysergic acid α-hydroxyethylamide and its decomposition products ergine and erginine using LiChrosorb NH₂ as the stationary phase and isocratic elution. The substances under study were determined by ¹³C and ¹H NMR and mass spectroscopy. The relative proportions of individual isomers of lysergic acid α-hydroxyethylamide, ergine and erginine in the fermentation medium are assumed to result from chemical equilibrium reactions. The method is reproducible and suitable for kinetic studies of the isomerization and degradation of lysergic acid α-hydroxyethylamide.

**INTRODUCTION**

Lysergic acid α-hydroxyethylamide (LAH) is an important substrate of semi-synthetic ergot alkaloids. In fermentation production, LAH¹ decomposes spontaneously² and is thus found in a mixture with ergine and erginine³. These compounds are also formed on heating ergotamine⁴; other products include C(8) and C(2') epimers. The same isomerization products were found to be formed on heating other cyclol alkaloids with dilute acid⁵⁻⁸. The analysis of these compounds was carried out by Bethke et al.⁹, who determined ergotamine and the products of its isomerization, hydrolytic and addition reactions by liquid chromatography on a reversed phase. Our aim was to elaborate a separation method for the isomerization and decomposition products of LAH. Because of the considerable instability of the compounds under study it was necessary to prepare reference samples from fermentation broth. The elaboration of the high-performance liquid chromatographic (HPLC) method was based on earlier results⁹.

**EXPERIMENTAL**

*Fermentation*

The method of cultivation of the saprophytic strain Claviceps paspali F 2056 and the conditions of submerged fermentation were described earlier¹⁰.

**Alkaloid extraction**
On the fourteenth day of fermentation the culture broth was adjusted to pH 9 with aqueous ammonia and extracted with chloroform-isopropanol (4:1); the chloroform layer was separated, dried over sodium sulphate and evaporated to dryness under reduced pressure at a temperature below 15°C. The crude extract was partially dissolved in chloroform, undissolved substances were filtered off and the solvent was evaporated. The crude extract enriched in iso-compounds was dissolved in chloroform-methanol (4:1) and used directly for semi-preparative liquid chromatography.

**Reagents**

Ergine, erginine, ergometrine and ergometrinine standards were obtained from Galena (Opava, Czechoslovakia). The solvents diethyl ether, chloroform, methanol, ethanol and isopropanol (Lachema, Brno, Czechoslovakia) were of analytical reagent grade and were distilled before use. The stationary phase was MicroPak NH₂, particle size 10 μm (Merck, Darmstadt, G.F.R.), in a ready packed column (50 cm × 8 mm I.D.) (Varian Aerograph, Walnut Creek, CA, U.S.A.).

**Instruments**

Semi-preparative liquid chromatography was carried out on an apparatus consisting of a VCM 300 high-pressure micropump and a variable-wavelength UV detector (both from Development Workshops, Czechoslovak Academy of Sciences, Prague, Czechoslovakia). The substances were eluted isocratically with diethyl ether-ethanol (9:1) as the mobile phase.

Mass spectra were measured on a Varian-MAT 311 instrument under the following conditions: energy of ionizing electrons, 70 eV; ionizing current, 1 mA; ion source temperature, 200°C; direct inlet system operated at 110-180°C. The elemental composition of the ions was determined by the peak-matching technique (± 5 ppm; perfluorokerosene standard).

¹H and ¹³C NMR spectra were measured on a JEOL FX-60 spectrometer (59.797 and 15.036 MHz, Fourier transform mode, 25°C) in a mixture of deuteriochloroform and perdeuteriomethanol (4:1). The CDCl₃ signal was used as a lock. Chemical shifts were referred to internal tetramethylsilane and were calculated with an accuracy of ± 0.005 and ± 0.06 ppm for the digitally obtained address differences.

UV spectra were measured on a Variscan LC instrument immediately during the qualitative determination by a stop-flow method.

**RESULTS**

**Liquid chromatography**
Analysis of an alkaloid mixture produced under submerged condition by the fungus C. paspali F 2056 revealed eight alkaloids in the extract. The elution times of four of them corresponded to ergine (V), erginine (VI), ergometrine (VII) and ergometrinine (VIII) (Table I, Fig. 1). The other four substances had elution times that did not correspond to any standard at our disposal and had to be isolated by semi-preparative liquid chromatography in order to determine their structures.

Semi-preparative liquid chromatography was carried out under the conditions given in the legend to Fig. 1. To obtain sufficient amounts of pure standard substances the chromatographic cycle was repeated 20 times; to prevent possible changes in the structures of the substances (isomerization, degradation), the individual fractions were immediately evaporated to dryness after each cycle under reduced pressure at 5-10°C. Analyses of the individual fractions showed that compounds I, II, IV and VI (Fig. 2) were obtained in pure form whereas compounds III and V were mixtures. The resulting standard compounds were used for identification.

**Identification of substances**

All components of the mixture analysed provided suitable UV spectra of Δ⁹'¹⁰-ergolene derivatives. The mass spectra (Table II) always exhibited an ion of m/z 267 (C₁₆H₁₇N₂O) and ions of the fragmentation series typical of ergine (V)¹¹. They are therefore substances derived from either ergine or erginine. The observed type of fragmentation and the character of the UV spectra preclude the presence of amides of Δ⁸'⁹-ergolenic acid (paspalic acid).

It is possible to distinguish the above derivatives by ¹H and ¹³C NMR spectroscopy. Compounds V and VI differ in the orientation of substitutent on C(8) (Fig. 2); in lysergic acid the substitutent is pseudo-equatorial whereas in isolysergic acid is pseudo-axial. The dihedral angle H(8)–C(8)–C(9)–H(9) in the former instance is close to 90°C, causing a small or zero value of J₈,₉; in the latter instance the protons are nearly staggered and the coupling constant may be larger. Using this rule, compounds II, IV and VI can be classified into an iso-series whereas I, III, and V belong to the normal series. The coincidence of the elution time of compound VI with that of an authentic erginine preparation (VI) confirms the correctness of this deduction.

Comparison of the ¹³C NMR spectra of the pairs ergometrine (VII)–ergometrinine (VIII)¹² and ergine (V)–erginine (VI) (Table III) indicates that the largest differences in chemical shifts are observed on C(7), C(8) and C(9). In the iso series the C(8) always resonates in a lower field and C(7) and C(9) in a higher field than in the normal series. The observed values (Table III) agree with the above classification. The non-stoichiometric ratio of the intensities of some signals in the ¹H NMR spectrum of fraction III–V indicates that this is a mixture of substances insufficiently separated by HPLC. Comparison with an authentic standard showed that compound V was ergine.

In the ¹H NMR spectra of compounds I, II, IV and mixture III–V (Table IV) the double resonance proved the presence of the CH₃CH(OH)NH–moiety. The carbon atoms of this group exhibit resonances at 21 and 70 ppm (off-resonance: quartet and doublet) in ¹³C NMR spectra (Table III). These findings allow one to interpret the peak with the highest m/z 293 in the mass spectrum as an M—H₂O peak (Table II). The compounds are therefore isomers of α-hydroxyethylamide of the isolysergic and lysergic acids. Compounds II and IV differ in the magnitude of the coupling constant between the NH proton and the secondary alcoholic group of the methine (< 1 Hz and 6.1 Hz); they are therefore epimers on Cₓ of the side-chain. Compounds I and III form a similar pair. The carbon atom Cₓ in isomers with higher J_NH,H₁ value (III and IV) resonates 0.7 ppm downfield of their counterparts I and II. Examples of epimers of lysergic acid dialkylamides hydroxylated in the side-chain were described by Ishii et al.¹³. Although they gave no values for the appropriate coupling constants, the recorded spectrum shows that the epimers also differ in the magnitude of the vicinal constant of the OCH proton. This is probably due to the different population of rotamers caused by different possibilities for hydrogen bond formation. The average conformation observed in the NMR spectra has similar values of chemical shifts for epimer pairs but different magnitudes of the coupling constants.

**Isomerization of LAH**

Isomerization of LAH isolated by semi-preparative liquid chromatography was accomplished according to Schlientz et al.².⁶. After alkalization with ammonia solution and extraction with chloroform-isopropanol (4:1), the reaction mixture yielded a sample that was analysed further by liquid chromatography. It contained approximately equal amounts of compounds II, IV and VI (8-10% each) and about double the amounts of I, III and V (about 20% each). The elution times of all substances corresponded to the elution times of compounds obtained from naturally occurring material. The results confirm earlier data²·³ indicating that ergine and erginine are probably only artifacts arising from LAH.

**DISCUSSION**

Isomerization of simple lysergic acid derivatives on C(8) is known to proceed readily even under mild conditions. With LAH, the reaction is more complex (as in cyclol alkaloids) as it also includes epimerization on asymmetric carbon atoms of the side-chain. Lysergic and isolysergic acid α-hydroxyethylamides (I, II, III and IV) are hemiacetals derived from acetaldehyde and ergine (V) or erginine (VI). The aldolization reaction is reversible. Mutual transformation of II to IV was observed during a 15-h ¹³C NMR measurement; the spectrum displayed signals of both C₂ atoms. The formation of isomers II, III and IV can likewise be observed during acid-catalysed isomerization of the parent LAH. The relative proportions of individual isomers of LAH (I, II and IV), ergine (V) and erginine (VI) in the cultivation medium during fermentation¹⁰ can be interpreted as the result of chemical equilibrium reactions.

The chromatographic behaviour of compounds I, II, III and IV is determined by the configuration on asymmetric carbon atoms C(8) and Cα. The pseudo-axial position of the side-chain on carbon C(8) may lead to the formation of an intramolecular hydrogen bond N(6)····H–N(20) which causes a marked decrease in the basicity of alkaloid molecules (II and IV); this is demonstrated by the reduced interactions with the basic nitrogen atom of the stationary phase. For this reason compounds II and IV are less retained on the column. The ¹H and ¹³C NMR spectra of individual diastereomeric pairs of alkaloids (I and III, II and IV) indicate that these substances differ in the population of rotamers with different possibilities of hydrogen bond formation and with different magnitudes of Van der Waals interactions, which is demonstrated by the different basicities of the molecules and thus in different interactions with the stationary phase.

The developed HPLC method can be used to study the kinetics of isomerization reactions and degradation reactions of LAH and for the control of the purity of preparations.

**REFERENCES**

1 F. Arcamone, C. Bonino, E. B. Chain, A. Ferretti, P. Pennella, A. Tonolo and L. Vero, Nature (London), 187 (1960) 238.

2 H. G. Floss and J. A. Anderson, in Steyn P. S. (Editor), Biosynthesis of Mycotoxins. Academic Press, New York, 1980, p. 17.

3 E. Kleinerová and J. Kybal, Folia Microbiol., 18 (1973) 390.

4 H. Bethke, B. Delz and K. Stich, J. Chromatogr., 123 (1976) 193.

5 W. Schlientz, R. Brunner, A. Hofmann, B. Berde and E. Stuermer, Pharm. Acta Helv., 36 (1961) 472.

6 W. Schlientz, R. Brunner, F. Thudium and A. Hofmann, Experientia, 17 (1961) 108.

7 H. Ott, A. Hofmann and A. J. Frey, J. Amer. Chem. Soc., 88 (1966) 1251.

8 A. T. McPhail, G. A. Sim, A. J. Frey and H. Ott, J. Chem. Soc., B, (1966) 377.

9 M. Wurst, M. Flieger and Z. Řeháček, J. Chromatogr., 150 (1978) 477.

10 A. Říčicová, M. Flieger and Z. Řeháček, Folia Microbiol., (1982) in press.

11 T. Inoue, Y. Nakahara and T. Niwaguchi, Chem. Pharm. Bull., 20 (1972) 409.

12 N. J. Bach, H. E. Boaz, E. C. Kornfeld, C.-J. Chang, H. G. Floss, E. W. Hagaman and E. Wenkert, J. Org. Chem., 39 (1974) 1272.

13 H. Ishii, M. Hayashi, T. Niwaguchi and Nakahara Y., Chem. Pharm. Bull., 27 (1979) 3029.

14 K. Roth, J. Magn. Reson., 40 (1980) 489.

**TABLE I**

**RELATIVE CAPACITY FACTORS, k'rel = k'i/k't OF SUBSTANCES i (II-VIII)**

| Compound i | k'rel |
|------------|-------|
| II | 0.44 |
| III | 1.37 |
| IV | 0.53 |
| V | 1.28 |
| VI | 0.63 |
| VII | 1.66 |
| VIII | 0.81 |

[image]

Fig. 1. Chromatogram of alkaloids I-VIII. MicroPak NH₂ (particle size 10 μm), ready-packed column (50 cm × 8 mm I.D.). Mobile phase, diethyl ether-ethanol (9:1). Flow velocity, 220 ml/h. UV detection: 310 nm, 0.50 A. Injection, 50 μl.

**TABLE II**

**MASS SPECTRA OF COMPOUNDS I-VI**

| Compound | m/z (rel. int. in %, composition) |
|----------|----------------------------------|
| I | 295 (14, C₁₈H₂₁N₃O), 293 (9, C₁₈H₁₉N₃O), 267 (100, C₁₆H₁₇N₃O), 249 (37), 224 (49), 223 (60), 221 (100), 207 (86), 196 (46), 192 (43), 180 (69), 167 (46), 154 (66) |
| II | 293 (4, C₁₈H₁₉N₃O), 267 (100, C₁₆H₁₇N₃O), 249 (16), 224 (26), 223 (30), 221 (56), 207 (54), 196 (45), 192 (20), 180 (46), 167 (26), 154 (40) |
| III + V | 295 (4, C₁₈H₂₁N₃O), 267 (100, C₁₆H₁₇N₃O), 249 (26), 224 (40), 223 (37), 221 (67), 207 (66), 196 (37), 192 (26), 180 (46), 167 (31), 154 (43) |
| IV | 293 (9, C₁₈H₁₉N₃O), 267 (100, C₁₆H₁₇N₃O), 249 (22), 224 (36), 223 (36), 221 (52), 207 (68), 196 (45), 192 (26), 180 (67), 167 (28), 154 (45) |
| VI | 267 (100, C₁₆H₁₇N₃O), 249 (22), 224 (37), 223 (35), 221 (67), 207 (72), 196 (46), 192 (29), 180 (57), 167 (52), 154 (56) |


[image]

Fig. 2. Structures of the investigated alkaloids.

**TABLE III**

**COMPARISON OF ¹³C CHEMICAL SHIFTS OF COMPOUNDS I–IV WITH MODEL COMPOUNDS**

| Position | Ergine* | Erginine* | Ergometrine* | Ergometrinine* | I** | II** | III** | IV** |
|----------|---------|-----------|--------------|----------------|-----|------|-------|------|
| C(7) | 54.7 | 53.9 | 55.6 | 54.0 | 57.8 | 54.8 | 58.0 | 53.8 |
| C(8) | 41.8 | 43.3 | 42.8 | 42.6*** | 42.6 | 43.4 | 42.6 | 43.4 |
| C(9) | 119.9 | 119.3 | 120.3 | 119.2 | 110.8 | 110.5 | 110.7 | 110.4 |
| Cₐ | — | — | — | — | 71.0 | 70.6 | 71.7 | 71.3 |
| Cᵦ | — | — | — | — | 21.4 | 21.6 | 21.6 | 21.4 |

* In d₆-DMSO.
** In CDCl₃ + CD₃OD (4:1).
*** Data from ref. 13, corrected on the basis of spectra measured by the technique in ref. 14.

**TABLE IV**

**COMPARISON OF SELECTED ¹H NMR DATA OF COMPOUNDS I-IV AND VI**

Spectra measured in a mixture of CDCl₃ + CD₃OD (4:1). δ-scale; coupling constants in Hz given in parentheses. Abbreviations: s = singlet; d = doublet; q = quartet.

| Compound | H₍₇₎ | H₍₉₎ | N-CH₃ | N₍₁₎-H | CONH- | CHOH α | CH₃ β |
|----------|------|------|-------|-------|-------|--------|-------|
| I | 6.90 s | 6.39 s | 2.67 s | 8.15 s | 8.78 s | 5.48 q (6.1) | 1.40 d (6.1) |
| II | 6.94 s | 5.98 d (5.5) | 2.61 s | 8.17 s | 8.68 s | 5.41 q (6.1) | 1.28 d (6.1) |
| III | 6.94 s | 6.45 s | 2.67 s | 8.39 s | 8.82 d (4.9) | 5.50 dq (6.1, 4.9) | 1.40 d (6.1) |
| IV | 6.92 s | 6.56 d (6.1) | 2.57 s | 7.96 s | 8.80 d (6.1) | 5.43 dq (6.1, 6.1) | 1.30 d (6.1) |
| VI | 6.94 s | 6.57 d (5.1) | 2.59 s | 8.11 s | 8.64 s | | |
Top