safety "rule" for 25x-NBOME, 2C-x, and DOx

[Solipsis]

Firstly: I agree with Nuke's post.

Secondly: this is IMO a typical case of SAR abuse. There is something called the SAR paradox which adresses the fact that often when we think we can see a pattern going on between structure and activity of a drug there are other factors that come into play to mess with our assumptions. How well a drug binds and what reactions and risks that yields depends on a great number of factors which indeed include the size of groups, electronegativity and how rigidly they are positioned.

Such rules as proposed in this thread are extremely instable which as is already said can be illustrated by comparing 2C-X's with their NBOMe counterparts. Adding the NBOMe group makes the whole molecule fit into a receptor differently. The halogens fit in a certain 'pocket' in the receptor and which halogen group fits better depends on how the rest of the molecule binds.
With a number of N-benzyl substituted 2C-X it seems indeed that the iodides are the most potent: they fit best to give the most activation of the receptor. I agree with Nuke that problems arising from this can be that these compounds act so well that the resulting activity can cause complications. In other words: in these cases the best explanation we seem to have for hospitalisations is that too much 5-HT2A activity can kill. Toxicity is not always a result of something inherently abnormal, destructive and alien going on, it is often the result of "too much of a good thing".

The fact that this seems the case with N-benzyl phens that have an iodide on the 4-position says nothing about whether for example 5-halogen-DMT drugs are a bad idea because "the halogen is alien". (In by far most cases the halogen group cannot "fall off" to cause problematic metabolites so that is not it either.) 5-halogen-DMT drugs may be bad or good only because of how the entire thing acts on receptors and what effects and side-effects that results in.

Another illustration is that there are bio-isosteres which means that some groups can act alike because they have properties that are similar like size and electronegativity. With research chemicals being developed, this is often used to create a drug that is similar to something else but not the same. IMO saying that some groups are by definition bad is misunderstanding that chemistry doesn't discriminate, there are only reactions to molecules having certain properties and if you can simulate the important properties well enough to make an analogue, receptors won't say "fuck you, I am not familiar with this", they will only react to how the ligand is built up in size and dipoles, etc etc.

Excusing this as correlations doesn't make it right - it is still an attempt to draw conclusions in a way that is only conductive to junk science.

Yes, the correlation you quote that is about halogens in the 2C-X range is definitely real within the 2C-X range of compounds, but this is nothing new and it seems like a pretty boring thing to say unless you are trying to take that point and applying it something else to draw conclusions.

Sorry to be blunt, it is not personal.

 

[neuron charge]

@ Solipsis CORRELATIONS are an important tool in SCIENtIFIC RESEARCH
so i'm not "excusing these as correlations"
you say, "we think we can see a pattern" imlying these correlations are not accurate... if so, how are they not, and where is the evidence?

also, i apologize if it was not made clear in the 1st post, but i said DOSE is FAR more important in terms of safety than any halogen correlations...

i did not say I is "toxic", and C is "safe"... i just drew out some CORRELATIONS between 2 variables... (i did blab about comparing endogenous atom sizes to these halogens, but that's outside the 3 correlations and obviously pure speculation...)

no need to apologize... obviously its not personal, i'd like to keep chatting about the subject to be honest

 

[Solipsis]

I repeat: correlations are either boring to throw out if you are not going to do anything with it and tricky if you are going to do something with it, which is often to see if you can try and draw conclusions from it.
That is how they are often used in research, otherwise just saying that would be an empty argument.

I said, the correlation can be correct within a limited scope, but can be invalidated by going beyond that scope because there are other factors to take into account.

The point is that it really seems like you want to claim rules from this as evidenced by your thread title, something that would be junk science because you are not taking the subtleties of SAR (structure activity relationship) theory into account.
If not, I don't understand where you are going with this and it would be helpful if you made that more transparent.
"Just drawing out some correlations" says very little to me. You are saying so yourself that it is only a tool. So I ask: what are you trying to achieve with it?

A lot of these chemicals need to be considered as unique, because simple homology (for example being able to say very simply that extending a group by one carbon makes it about half as potent each time) is more like exception than rule.
I understand that it is easier to try and categorize drugs in your head, and it is certainly true that for example amphetamines bear resemblance to each other, 4-HO tryptamines bear resemblance to each other, etc. but you just need to be very careful making any blanket statements especially when you change something big on a molecule like hanging an NBOMe group on it.

As far as I am willing to go here is to say that within the family of N-benzylated phens including the NBOMe's NBMD's and NBOH's it seems that the 25I substitution is the most potent one. We can further induce that these 25I-NBX compounds carry the most risk since as it seems at this moment the 5-HT2A agonism itself can be toxic. But we cannot generalize more about the iodide moiety itself.

And yes my problems were especially with the exogenous atom size argument.
Also, the copious amount of capital letters is not really necessary. If you need them to convey your point, your point may be a weak one.

 

[Transform]

I'm sorry to be blunt but I do not think you understand this issue well enough to comment on it OP. Normally I would stay out but this misnformation may lull someone into a false sense of security with non-halogenated molecules, potentially ending badly.

The appeal to nature fallacy remains a fallacy on this occasion. The fact that these molecules contain organohalides means nothing.

 

[neuron charge]

...as i feared, this thread was a lost cause
most are not familiar enough with the concept of CORRELATION vs CAUSATION
...thread can be closed if needed, i guess i have nothing else to comment on

you don't want to acknowledge the 3 correlations?
ok fine... PIHKAL does, Erowid.com does, as well "Fluorine in psychedelic phenethylamines"

...sole purpose of the post was to assist in HARM REDUCTION, NOTHING ELSE

...i apologize if i'm coming off like a self-important dick. i have the best intentions... carry on fellow bluelighters... PEACE

 

[Transform]

I'm actually now not entirely sure what you're saying the correlation is to be honest?

The inclusion of a certain halide does not guarantee anything, nor does it cause a trend across multiple classes.

 

[Psichedelic]

http://www.ncbi.nlm.nih.gov/pubmed/15801832

Anyone have any thoughts on this?

I believe that it claims some 2c-x, DO(x), and 25x-NBx substances as MAOI (MAO-A Inhibitors).

I cannot get through the pay to read, expansion would be nice.

Link Abstract:


Sulfur-substituted alpha-alkyl phenethylamines as selective and reversible MAO-A inhibitors: biological activities, CoMFA analysis, and active site modeling.
Gallardo-Godoy A, Fierro A, McLean TH, Castillo M, Cassels BK, Reyes-Parada M, Nichols DE.
Source

Department of Chemistry, Faculty of Sciences, Universidad de Chile, Casilla 653, Santiago, Chile.
Abstract

A series of phenethylamine derivatives with various ring substituents and with or without N-methyl and/or C-alpha methyl or ethyl groups was synthesized and assayed for their ability reversibly to inhibit monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds showed potent and selective MAO-A inhibitory activity (IC(50) in the submicromolar range) but none showed appreciable activity toward MAO-B. A three-dimensional quantitative structure-activity relationship study for MAO-A inhibition was performed on the series using comparative molecular field analysis (CoMFA). The resulting model gave a cross-validated q(2) of 0.72 and showed that in this series of compounds steric properties of the substituents were more important than electrostatic effects. Molecular modeling based on the recently published crystal structure of inhibitor-bound MAO-A provided detailed evidence for specific interactions of the ligands with the enzyme, supported by previous references and consistent with results from the CoMFA. On the basis of these results, structural determinants for selectivity of substituted amphetamines for MAO-A are discussed.

PMID:
15801832
[PubMed - indexed for MEDLINE]

 

[Solipsis]

@Psichedelic: that paper is about sulfuric amphetamines, basically DOT-X but they were called names like Aleph-# instead.
It's interesting and it seems to suggest that 2C-T-X may be MAOIs as well which has been suspected for a long time - but the scope here is the amphetamine analogues.
None of it is necessarily relevant here - maybe it would be if we knew that NBOMe casualties all died of a serotonin syndrome like event, I don't even know if we can say that about 2C-T-X casualties.

@Bloodshed: [edit: tangent argument resolved]

@Neuron: you were already asked politely to elaborate on the matter, I tried to do it for you by confirming that IMO:

...within the family of N-benzylated phens including the NBOMe's NBMD's and NBOH's it seems that (edit: of the 2,5-dimethoxy-4-halo series) the 25I substitution is the most potent one. We can further induce that these 25I-NBX compounds carry the most risk since as it seems at this moment the 5-HT2A agonism itself can be toxic. But we cannot generalize more about the iodide moiety itself.

The 5-HT2a agonism seems to be potentially dangerous if taken far enough, but it is also what people are looking for because it is considered equal to psychedelic power. With many other drugs we see this as well: with methamphetamine or heroin the MOA is inherently both risky and satisfying.

Something that may be unaccounted for is that if 25I-NBOMe is the most popular one, you would expect more casualties even if the risks were identical to that the other halogenated ones in the series - just because it is more prevalent!. 25B-NBOMe has been said to be potentially fatal in those who have an unusual sensitivity or metabolic deficit. And I hypothesize that the same is true for the Chloro, even if we haven't seen it yet... because some kind of enzyme deficiency would probably not differentiate as much between what 4-substitution is on there as a 5-HT2a receptor.

So while we should take the iodinated ones seriously, and the correlation you are speaking of is - sorry to say - virtually a given, it is hard to depart from there.

Personally I don't really feel like investing much more attention in all the N-benzylated phens or only as a curiosity, but if I was more involved I would be interested in seeing if the effects of the NBOH's and NBMD's are more attenuated. Maybe the psychedelia is less extreme but it should still be extreme enough if we can reduce the risk by switching to them. Unfortunately that is entirely speculative and we might be switching to compounds that are killers far more than any NBOMe is.
I guess time will tell.

I agree with Transform that you don't sound like you really understand what you are talking about even if you had a revelation about correlation vs. causation. Finding correlations says fuck all if you are not going to do anything with it, like postulating, theorizing hypothesizing and investigating further.
If you keep repeating the same things ultimately the thread would have to be shut down because all of us having a clear enough understanding where you are going with the topic is a fundamental criterium for a meaningful thread.

 

[neuron charge]

...hey guys i'm back. please re-read 1st post. i have spent some time getting my thoughts together and the original post was very disorganized/crappy...
besides that, nothing else to report

@ Solipsis - yes your right. nothing new here [i realize when pihkal was published]
...just wanted to do 1 posting for BL and to assist in harm reduction concepts especially when it comes to nbomes (people are waging their lives on this shit when doses aren't right)
...i have read your musing for some time, and i plan on continuing :]

 

[Solipsis]

I hope I wasn't too harsh As I re-read our post I realised that it may appear that way.. I do encourage these inquisitions, preferably not in the form of an argument but instead dialectics.

EDIT:

Discussion about sulfuric amphetamines and MAO inhibition is moved to it's own thread here.

 

[titan7]

In reality we don't know if 25c,b(etc) are capable of killing people. It's more than likely that they are just as deadly as 25i. 25i was the first to market so plots of dumb inexperienced people got a hold of it in large quantities. My vendor snorted 25mg of 25i (he was hoping to die actually) in one line, I don't know if he had a tolerance or whatnot but it goes to show how strange these drugs are. People are dying from less than 1mg meanwhile people (myself included) are taking doses that should've killed them and surviving.

 

[johhnya541]

I have permanent brain damage from a 25i-nbome overdose. It caused vasoconstriction and heart arrhythmia's for me. I now suffer from severe anxiety, depression, and amnesia. Some fukk stick at Electric Forest 2012 dosed me with a puddle in my hand saying it was "really clean orange sunshine from the 70's" BOOM, half hour later I was puking my brains out followed by blinding visuals. Swirling colors and patterns. Heart started pounding out of the side of my chest. I haven't been the same since. Its been over a year........ Don't fuck with these compounds... Not worth it. Madd people have died bc of this shit.

 

[Xtc <3]

How do you know it was 25-I you were given???

I hope you manage to make a recovery, about 3 months ago at a party this lad had a gram bag of the stuff and was selling capsules to anyone and everyone for them to sniff. He was literally eyeball dosing up so many people with 25-I out of this backpack.

I was trying to warn people buying from him but they wouldn't listen, God knows how those people handled their trips that night. Freaked me (already on 2C-B) right out.

 

[Si Dread]

& that is exactly what prohibition has done to increase the risks already inherent in this activity... Ignorance simply multiplies the risks.

 

[infantannihilator]

I have permanent brain damage from a 25i-nbome overdose. It caused vasoconstriction and heart arrhythmia's for me. I now suffer from severe anxiety, depression, and amnesia. Some fukk stick at Electric Forest 2012 dosed me with a puddle in my hand saying it was "really clean orange sunshine from the 70's" BOOM, half hour later I was puking my brains out followed by blinding visuals. Swirling colors and patterns. Heart started pounding out of the side of my chest. I haven't been the same since. Its been over a year........ Don't fuck with these compounds... Not worth it. Madd people have died bc of this shit.

When you say they dosed you "with a puddle in your hand" what exactly do you mean - They poured a liquid into your hand I would assume?
You then did what with it - slurped it up and swallowed it? Kept it in your mouth? Snorted it? NBOMe is not orally active at all, so you would have had to snort it or hold it in your mouth for a while

Being told that it was "orange sunshine from the 70s" combined with the above leads me to wonder just how you came to the conclusion you were given 25i, or any NBOMe for that matter..

I'm sorry you've gone through what you've gone through and I hope things turn around for you, but I have to seriously question the validity of your story. To me your claims are entirely baseless and nothing but bullshit propaganda. From the sounds you cannot be sure what you were given at all, and no offense but this is a case of your negligence more than anything: you willingly ingested an unknown compound given to you by an unknown person - you fucked up. I have good reason to believe you weren't entirely sober at the time you made the decision to ingest this mystery liquid either, hello unknown interactions.

No "madd people" haven't died. There are a few cases in the news where 25i is suspected to be the culprit, largely in part due to it being the new 'fear inducing' mystery drug, and many of those deaths weren't caused by the drug directly. This does not mean the drug is safe - but it can be taken safely and effectively.. it is ignorance on the part of users and dealers looking to make a quick buck that is the problem.

I don't mean to be a dick, I really don't, but stories like this grind my gears because you're just spreading misguided ignorance.

 

[neuron charge]

@titan7: no one is sure at this point which nbome is "most dangerous", when dosage is accounted for. HOWEVER... due to these "halogen correlations", nbome deaths being reported almost exclusively as 25i, erowid nbome difficult experience reports heavily favoring 25i, and BL forums declaring C the "softest" of the 2C-x family,

you would rather overdose on 25c than 25i (or rather overdose on 2C-C than 2C-I)

...you say your not sure whether 25b or 25c could kill?
almost all "psychedelic phens" can kill if the dosage is high enough, so it is VERY unlikely 25b or 25c would be any different

...IMO the BROAD dosage range reported for nbomes has MORE to do with "NBOME purity" than "individualistic reactions" (although there is no doubt individualistic reactions play into this to some extent) thx for the post

 

[Thumbsup.]

The only safety rule to RC's.. is don't do them.

 

[infantannihilator]

25i is also the most prevalent and most widely used and distributed of the 25x's.. its also been sold as acid. You'll note a number of those difficult experiences were just that - people who acquired 25i sold as acid.

Not everyone who uses erowid is a careful user who puts in effort researching and following meticulous testing out of compounds on themselves. I often wonder just how some of the experience reports on there ever get published.. there are a few I've come across that are nothing more than a few sentences that boil down to "horrible substance I hated it and had the worst time of my life and NO ONE should ever use this."

I propose this: instead of talking about "all these reported deaths" how about you actually link them?

In all my research I've only come across ONE that is a supposed direct result of 25i causing death, and this is the case of the man at a festival who snorted "a drop" and then later died. One, its "suspected" that 25i was the substance in question - not proven. Two, nothing else is mentioned, nothing about what else he was on, what conditions he had and so on and so forth. Its tragic the man died but on the other hand the news pieces serves as nothing more than a scare tactic and "proof" that we need to be more vigilant in tracking down and stopping drugs in our society.

The other deaths I am aware of involve people doing stupid things while high out of their minds that result in death; falling off balconies, running into poles, etc.

There is one report I am aware of where a man ended up in the hospital after ingesting 500ug, suffering from severe vasoconstriction, had blacked out and apparently was low on potassium or something like that.. This report is highly questionable and suspect to me personally, but we'll never know.

There is even a thread here on bluelight that I personally find highly suspect where a user reports having a seizure after ingesting 4.5mgs and breaking both his arms and so on.. yet hes posting perfectly fine from a hospital bed from his phone less than 24h after and a lot of his story doesn't add up. Now why would someone make something up? I have no idea why anyone would, but still, the whole thing is fishy to me.

You also must take into consideration that it is human nature to make the effort to point out negatives.. most people who have decent experiences aren't going to put the effort in to write up a report because they had a good time but nothing really eventful or worth writing about happened.. but someone who has a horrible time is more likely to go and write about it and warn everyone off of it.. this is the same for people buying electronics or cars or shoes or anything in society.. its human nature to dwell on negatives.

Now none of this means 25i is safe and can be approached carelessly.. but you have to take into account what is left out of these news articles and the bias involved in them in regards to painting drugs as evil horrible baby killers. You must also take into account the prevalence of this particular substance in regards to the others of the same nature.. The media has lied time and time again.. you can't just take these reports at face value, and you certainly can't use them to back up your, imo, fruitless correlations.

I dont mean offense to anyone, but I just personally question everything that comes my way and I am highly skeptical to anecdotal reports that leave out any sort of evidence and boil down to a warning not to do something because it went bad for them. I see this mentality everywhere I go in life and it drives me absolutely nuts. Someone I know posted a link about Iraqi birth defects on my facebook yesterday, and how it is the result of US shelling of depleted uranium bombs, and these people just take it at face value and don't even question it, jumping right into their circle jerk of anti-US, anti-government, anti-everything, thinking they are enlightened and better than other people.. it just absolutely blows my mind. People like this who just take what is fed to them and fail to question are the reason why it feels like nothing is getting accomplished in our societies today. Its an endless sea of shock-gossip purported to be truth and its absolutely mind numbing.

 

[neuron charge]

@ infantannihilator yes your right. erowid/BL stories are not data, only stories...
as for the nbome deaths, i follow many drugs on the google news feed. i have seen a number of deaths "REPORTED" for i and a few for b, and maybe only 1 for c...
i'm not gonna take the effort to find these for you sorry (use google)
i'm not trying to stir up FEAR, i'm just trying to stir up more CAUTION/SAFETY/HARM REDUCTION

 

[infantannihilator]

I know you're not, but I'm simply trying to point out that you can't use the fact that you saw these substances mentioned in a news article as proof of their propensity towards death.

These are the news articles related to 25i deaths as posted on erowid with my commentary below:

Incident: Krystopher Sansone, 2013
In Feb 2013, 17-year-old Krystopher Sansone died in Orange County, FL after insufflating a powder that has been reported by the media to have been "bath salts", but by the coroner as "NBOMe". Four others were also hospitalized, but recovered. It is not clear whether the substance involved was 25I-NBOMe or another in the NBOMe series.
Orlando Sentinel. "Bath salts to blame for teen's fatal overdose, Medical Examiner rules". Orlando Sentinel. Orlando, FL, USA. Apr 5, 2013.

Garavaglia [Medical Examiner] determined that Sansone died as the result of an accidental, "apparent" overdose to "NBOMe."

So the coroner determined it was an NBOMe but didn't know which kind. Now just how did he do that? I would think if he could determine it to be an NBOMe then he could determine the type. Nonetheless, these kids insufflated the pure powder.. This is absurdly dangerous and I think everyone here on bluelight knows this. This is the result of ignorance and user error.

Incident: Clayton Otwell, 2012
In October 2012, 21-year-old Clayton Otwell died in New Orleans, LA, after insufflating a drop of 2C-I-NBOMe at a festival. The material was in a liquid of unknown potency. Otwell is said to have been ingesting caffeinated alcoholic drinks for several hours beforehand.
Times-Picayune. "21-year-old dies after one drop of new synthetic drug at Voodoo Fest". Times-Picayune. New Orleans, LA, USA. Nov 1, 2012.

As Newell watched, her friend knelt and the stranger plopped a single drop from a vial into Otwell's nose. Otwell immediately started babbling incoherently, Newell said. She got him to the medical tent at the festival, but within 30 minutes, he had a seizure and never regained consciousness. Taken to Tulane University Hospital, he was placed on life support Saturday night; he died Tuesday.

This is the one aforementioned report. He was apparently ingesting caffeinated alcoholic drinks for hours, that certainly had an effect.. Also potency was entirely unknown, and really who knows if it was 25i. It comes on really fast nasally, but to immediately begin incoherently babbling? Granted I've not taken a very large dose but even when shit was melting out of my vision, words became impossible to read, the walls around me flashing different colours and so on, I was pretty much entirely there upstairs and could have coherent conversations inbetween the insane body rushes.. Something doesn't add up.

Incident: Stephanie Chappell Hobson, 2012
In July 2012, 25-year-old Stephanie Chappell Hobson died in North Carolina, USA, reportedly after consuming 25I-NBOMe with her boyfriend. The material was in "pill" form, so dosage is unknown. However analysis of the pills suposedly found that they did contain "25i" (Another name used for 25I-NBOMe). Hobson died more than 12 hours after taking the substance.
WECT6. "Man arrested in connection to death of girlfriend". WECT6. Wilmington, NC, USA. Aug 20, 2012.

Analysis of the pills found at the Tesla Park apartment confirmed they are the hallucinogenic drug 25i. Leutgens was impaired when his girlfriend experienced problems with the drug. David said the suspect called other drug dealers before calling 911, which created a delay in the emergency care she needed.

StarNewsOnline. "Friend charged in woman's fatal overdose". StarNewsOnline. Wilmington, NC, USA. Aug 20, 2012.

Stephanie Chappell Hobson, 25, languished for 12 hours July 18 after taking a synthetic drug provided to her by her boyfriend Jeremy Leutgens, said District Attorney Ben David. In that half a day Leutgens reached out to other users of 25i, a potent hallucinogen outlawed by federal law but not by North Carolina, for advice on what to do, David said.

25i pills?? This just doesn't make any sense to me. Why would anyone make it into a pill? Its not active orally.. It was supposedly confirmed by analysis but how does this even sound right? The fact that the article goes on to say that its outlawed by federal law (which it is not), makes me even more skeptical that the article is entirely factual..

Incident: Elijah Stai, 2012
On June 12 2012, 17-year-old Elijah Stai died in Minnesota, USA after consuming 25I-NBOMe which he reportedly thought was a mushroom extract. Reportedly he and a few friends mixed the chemical with melted chocolate and ate them. He exhibited significant serious negative physical effects before "passing out, never to wake again". Some news reports have been incorrectly referring to 2C-I-NBOMe "2C-I", which is a different chemical.
CityPages. "Adam Budge, 18, charged with murder following friend's synthetic drug overdose". CityPages. Park Rapids, MN, USA. June 21, 2012.

An hour later, Stai began "freaking out" and acting as if he were "possessed," foaming at the mouth, hyperventilating, and smashing his head against the ground. Budge and other buddy laid Stai down in a bed and placed a wet towel on his head to cool him down. By 1:30 in the morning, Stai was no longer breathing.

Inforum. "18-year-old charged with murder after Park Rapids teen dies from drug overdose". Inforum. Fargo-Moorhead, USA. June 20, 2012.

Police recovered a small baggie containing chocolate from Stai's pocket and Adam Budge gave police an empty baggie labeled "25iNBOMe," which were sent to the Minnesota Bureau of Criminal Apprehension. Forensic scientist Amy Granlund identified that the psychedelic substance was indeed "25i-NBMOe," otherwise known as 2C-I.

This just doesnt even make sense here, they mixed it with chocolate and ate them? 25i is not active orally so explain that one to me.

Incident: Christian Bjerk, 2012
On June 11 2012, 18-year-old Christian Bjerk died in Minnesota, USA after consuming 25I-NBOMe. He was found dead on a sidewalk in Grand Forks. The chemical was reportedly bought by a friend of Bjerk from Adam Budge, the same source in Elijah Stai's death.
Inforum. "Grand Forks man appears on drug charges in Fargo". Inforum. Fargo-Moorhead, USA. August 7, 2012.

Christian Bjerk was 18 when he was found dead early on June 11 along a city street after ingesting a hallucinogen that investigators say originated with Spofford.

This article literally gives no information at all. Just man died, supposedly consumed 25i.

In all of these cases, if 25i is the true culprit, the main cause of death is massive amounts of user ignorance and negligence. I mean, most of them dont even make sense at all, but they clearly werent taking measured doses, nor does it sound like they had any idea what they were doing at all and were just looking to get fucked up at any cost.

I mean.. clearly, this isnt the worlds safest compound, but neither is really any compound if you don't put any thought to it and just wildly take it without regard..