5-substituted tryptamines

[Recept]

I am not sure whether this belongs in PD or ADD, so mods, move if neccessary. Also, I couldn't find anything with the search, I'm sorry if this has been discussed before.

Anyway, given the recent discussion on bufotenine (5-HO-DMT) here on BL, I've been starting to wonder about 5-substituted tryptamines in general. More specifically, the 5-hydroxy-dialkyl-T's.

In TIHKAL, Shulgin addresses only bufotenine, but concludes: "At the bottom line, I do not really know of bufotenine is a psychedelic drug. Maybe yes and maybe no." My guess is it has to do with it's apparent toxicity profile and he didn't even pursue it's analogues for that reason. However, in the light of recent discussion, it seems like this drug is very different from it's relatives in that it seems to act completely differently in it's different forms (freebase, different salts etc). Now, I'm no expert, but I would guess it could have something to do with how it crosses the BBB (in some forms, it seems to be better at that, leading to decent psychedelic activity, while in others it seems to produce next to nothing other than toxic peripheral effects).

According to reports, in some forms (namely calcium bufotenate, and free base), it is a proper psychedelic with effects similar to those of psilocin and DMT. Some go as far as to claim it's actually better than either of those due to it's length of action (two or three hours as opposed to the 6-hour ride of mushrooms or 15-minute flash of smoked DMT), which I gotta say does sound appealing indeed.

All of this leads me to wonder, what if it is similar to other analogs as well? I for one would be more than happy to see a 2-hour version of miprocin, iprocin, etc. Of course, with those chemicals, the length of action profile might not be similar, but still, things like 5-HO-MiPT, 5-HO-DiPT, 5-HO-DPT, 5-HO-MET, etc might be an interesting area to explore. Or am I completely off here? Any thoughts on this would be much appreciated.

To take this even further, how about esthers of these molecules, such as 5-AcO-DMT and the like? Could also be interesting to explore, no?

Of course I realize, that even bufotenine has not yet been properly researched in many aspects (other than it's widely known to be used in native snuffs for a long time!), just throwing ideas out there to see what others think of these potential areas to explore some time in the future of psychedelic research. Also, if anyone knows of any information on this subject, a push in the right direction would be much appreciated.

So anyway, discuss!

 

[swilow]

I will moce this to ADD- vektor and f-b please move back forthwith if you choose

 

[MattPsy]

I'd be interested in 5-AcO-DMT because it's likely it would have less peripheral effects than 5-HO-DMT (Bufotenine).

 

[nuke]

From SAR studies 5-OH-DMT should by all accounts be very active (probably close to 5-MeO-DMT), so long as it gets to the brain. It has a fairly low LD50 in rats (250mg/kg), about twice that of 5-MeO-DMT, and appears to be a strong serotonin agonist.

5-AcO-DMT could cross the BBB and then be metabolised into bufotenine; it may constitute a very active form of bufotenine (the body can cleave acetoxy groups with greater ease than it can methyl phenyl ethers).

However, this is still likely to be eaten up quickly by MAO-I any other route but smoking or snorting and maybe rectal or intra-whatever. Other 5-AcO-Ts may prove to be very interesting though.

If you substitute larger alkyl ethers on the five position you'll probably see compounds devoid of actvity beyond ethyl because it screws up the binding in a crucial part of serotonergic 2 receptors.

 

[retired_chemist]

Frankly, I think most of these "alternative" tryptamines are pretty marginal. Once they become scheduled (and it is in the works) I don't see anyone continuing to seek them out.

From what the OP described as desirable, DET is the one you are really looking for. Shulgin's accounts of it are sadly understated, and are mostly representative of poor choices in administration.

Base, smoked from glass or saturated onto a small amount of low grade marijuana as a vehicle only (don't want to step on the effect too much) is the only way to go.

Some almost immediate mild nausea after the first hit is the only side effect. I'm a firm believer that with any psychedelic if you feel the need to puke, just do it. Take the first hit at a sink, puke, it happens once and passes immediately, drink a little water then finish the rest.

Rapid but gentle come up, modest visuals, spectacularly empathic, gentle but genuine insightfulness (something I think most phens fall short on). The peak lasts maybe an hour+, the comedown is extremely gradual over another hour. Absolutely no negative after effects, the after experience is a sense of warm, comfortable fulfullment.

IMO LSD is the premier fullblown psychedelic. DET is like it's little sister that you have a warm intimate relationship with.

Unfortunate that it has always been uncommon. If more people had experienced it the demand would be huge.

I'm retired, lol but find a good chemist - it;s easily prepared by the Speeter-Anthony synthesis. A good fume hood is essential, the stench of both indole and the N,N-diethylglyoxalamide is very persistent.

Good luck in your quest.

 

[egor]

I would still love to try 5-ethoxy-dmt

 

[MattPsy]

retired_chemist: The references I have on Speeter-Anthony syntheses say debenzylation is needed at the end of the synthesis but it does not mention how this is performed, yet I am curious to to know. Can you tell me in a roundabout way that does not break BL's terms of use (ie, a method name) ?

Oh also, what do you think of 5-HTP as a potential other synthetic route? Ethanoylchloride to add the 5-acetoxy group, decarboxylate, and then methylate the amine with DMS or DMC or MeI? Or perhaps that free hydroxyl group (at -5) would need protecting first and then form the ester later on in the piece, but i'm not sure the best way of going about this)

 

[vecktor]

retired_chemist: The references I have on Speeter-Anthony syntheses say debenzylation is needed at the end of the synthesis but it does not mention how this is performed, yet I am curious to to know. Can you tell me in a roundabout way that does not break BL's terms of use (ie, a method name) ?

Oh also, what do you think of 5-HTP as a potential other synthetic route? Ethanoylchloride to add the 5-acetoxy group, decarboxylate, and then methylate the amine with DMS or DMC or MeI? Or perhaps that free hydroxyl group (at -5) would need protecting first and then form the ester later on in the piece, but i'm not sure the best way of going about this)

catalytic hydrogenation.

you should look up the thermal cyclisation of 5 substituted tryptamines as this would preclude thermal decarboxylation.

V

 

[MattPsy]

Ah crap true, I hadn't considered that they might break down under those conditions . That is a real problem.

 

[retired_chemist]

I'm not suggesting anyone do anything illegal.

I merely pointing out the compound you are looking for in a 5 OH tryptamine derivative - low toxicity profile, 2 hour experience, full dimensional experience - already exists, N,N-diethyltryptamine.

Alkylation, and especially methylation of amines is never attractive unless you want to go all the way to the quat ...

 

[Jabberwocky]

Yes, I would love to try DET. The spice of China.

 

[Recept]

^ Same here, I've been very interested in N,N-DET for quite some time now, unfortunately it's not available to me

5-AcO-DMT could cross the BBB and then be metabolised into bufotenine; it may constitute a very active form of bufotenine (the body can cleave acetoxy groups with greater ease than it can methyl phenyl ethers).

However, this is still likely to be eaten up quickly by MAO-I any other route but smoking or snorting and maybe rectal or intra-whatever. Other 5-AcO-Ts may prove to be very interesting though.

Yes, oral route is mainly out of the question, but the duration of bufotenine seems very nice via the intranasal and smoked route as well, probably IM would be the best way to go if one had the pure compound.

Frankly, I think most of these "alternative" tryptamines are pretty marginal. Once they become scheduled (and it is in the works) I don't see anyone continuing to seek them out.

I don't know about that, personally I like miprocin a lot, it is very similar to mushrooms but has it's own specific signature that makes it pretty worthwile to me. Iprocin/ipracetyl also seem nice (though my experience with those is limited), they are like the light version of entactogen/emphatogen tryptamines (AMT being the proper "tryptamine ecstacy"). I haven't tried 4-HO-DET, but wouldn't hesitate for a second should the opportunity present itself. 4-HO-MET also seems interesting from the few reports that are available.

So, I definately wouldn't discard those "alternative tryptamines", though anything-DMT seem to be the "prime" ones without question. I guess you could make the same comparision with mescaline and all the 2C-s/DOx as well, huh? Still doesn't make those not worthwile IMHO.

IMO LSD is the premier fullblown psychedelic. DET is like it's little sister that you have a warm intimate relationship with.

That's a nice way of putting it. Makes me want to try DET even more

 

[nuke]

4-HO-DET is great stuff. Same with 4-AcO-DET. Though there can be a lot of tremors.

 

[fastandbulbous]

I've got a feeing that despite improved BBB penetration, the peripheral side effects from hydrolysis of the compound will be as bas if not mnoreso than 5-methooxytryptamines.

Just a feeloing though, nowt to back it other than my sense of foreboding

 

[retired_chemist]

OK, maybe I should have phrased it better. Any of the 4-O trypts seem reasonable to me for exploration, they come from a good lineage.

OTOH the 5-O trypts, and some of the other ones seem "marginal" to me in the respect that the effects don't really sound that great and the toxicity profiles seem relatively high.

2C-Xs are OK, fun occasionally but a little shallow. I would not personally touch any of the 2C-T-#s. I thought briefly (like for about 5 minutes) about acquiring a little 2C-T-2, then realized I would never be willing to do it. Just because you can make a thioether analog of an ether does not make it a good idea. Maybe I'm prejudiced because I did a lot of unrelated thioether chemistry as part of my graduate research. (R-S-CH2CH2X -> vinylsulfones if you really want to know). Nasty nasty compounds.

2C-E I like, even though the physical aspects are a little unpleasant.

DOXs - worthwhile for some people, a few times. But the cavalier attitude I seem to perceive about these is very disturbing. They are definitely not party favors, and I don't think they are really even suitable for mainstream use.

I was at a 2004 Dead show, decided what the hell it's been a long time, why not. Except what I got were "bitter blotters". After about 45 minutes I decided, OK, times have changed, no big deal, shelled out some bucks for blanks. By the end of the first set I realized they weren't blanks after all.

Now if the kid had said it's DOI, or it's DOC (I know DOB, this stuff was just slightly different) that would have been cool. I woulda said, thanks but no thanks, I'm just not that young anymore.

But he did not. And he's lucky as hell it was a big outdoor show because if I had seen him again I did not have any drugs on *me* and I would have dragged his punk phony ass to the nearest cop and said "This kid - cuff him and then search him for blotters- he's selling some kind of bullshit he says is LSD and that's definitely a crime." Skinny white kid in the county lockup in this particular metro area? Would not have mattered much to me if he never got prosecuted - he woulda definitely gotten schooled.

People that can't be responsible with something should not have it. You see, it's not really the compounds that are marginal. They are just compounds. It's people that are marginal. And when I look at this board, I see some knowledgeable people, but sorry if I step anyones toes - I also see a whole lot of really marginal people....

 

[akThrash]

DET is like it's little sister that you have a warm intimate relationship with.

Umm thats a little disturbing and a little revealing.

 

[Recept]

OK, maybe I should have phrased it better. Any of the 4-O trypts seem reasonable to me for exploration, they come from a good lineage.

OTOH the 5-O trypts, and some of the other ones seem "marginal" to me in the respect that the effects don't really sound that great and the toxicity profiles seem relatively high.

I can relate to that, many of the 5-MeO-Ts do tend to have quite toxic side-effects, and bufotenine is still kind of controversial although in light of recent discussion this one seems to act quite differently in different forms. One of the main reasons I started this thread was to provoke more discussion in this area, so perhaps a better conclusion can be reached one day.

2C-Xs are OK, fun occasionally but a little shallow. I would not personally touch any of the 2C-T-#s. I thought briefly (like for about 5 minutes) about acquiring a little 2C-T-2, then realized I would never be willing to do it. Just because you can make a thioether analog of an ether does not make it a good idea. Maybe I'm prejudiced because I did a lot of unrelated thioether chemistry as part of my graduate research. (R-S-CH2CH2X -> vinylsulfones if you really want to know). Nasty nasty compounds.

Well, the only 2C-T-x I've tried is 2C-T-7 and that one seemed very interesting to me, despite being a bit nasty on the body. I suppose these being worthwhile is a rather subjective matter, but I for one certainly intend to explore this class a bit further in the future.

2C-E I like, even though the physical aspects are a little unpleasant.

DOXs - worthwhile for some people, a few times. But the cavalier attitude I seem to perceive about these is very disturbing. They are definitely not party favors, and I don't think they are really even suitable for mainstream use.

I feel exactly the same about 2C-E. And DOx are powerful psychedelics indeed and deserve to be taken way less lightly than many people apparently do.

 

[akThrash]

Its the hype man. Most people have little to no knowledge of so-called "exotic" drugs and their friends have even less. So when they see a new drug that seems appealing and they happen to stuble upon a source (Which luckily happens rarely) it COULD have extreme adverse effects.

 

[hamhurricane]

I would not personally touch any of the 2C-T-#s. I thought briefly (like for about 5 minutes) about acquiring a little 2C-T-2, then realized I would never be willing to do it. Just because you can make a thioether analog of an ether does not make it a good idea. Maybe I'm prejudiced because I did a lot of unrelated thioether chemistry as part of my graduate research. (R-S-CH2CH2X -> vinylsulfones if you really want to know). Nasty nasty compounds.

retired chemist I find this very interesting could you elaborate on why you think they are nasty compounds?

 

[retired_chemist]

Anyone who has ever done much thiol or thioether chemsitry will tell you it's pretty nasty stuff. Most of the compounds I worked with i.e. R-S-CH2CH2-X and some RSO2CH=CH2 compounds are severe blistering agents.

Maybe I should have made it clearer I was speaking of my own experiences with an unrelated set of compounds. I realize 2C-Ts are not the same thing. So call it personal prejudice - the thought of it gives me the creeps. Reading about the reported side efects does not do anything to alleviate my inherent unease with this whole class.

But I'm just a chemist. I can't say I have any rational basis for thinking these compounds are maybe not such a great idea. I think F&B has some background in pharmacology - you would probably be better served by what his thoughts on these compounds are.