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4-AcO-DMT stability, other variations of DMT?

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yaesutom

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I'm wondering about the stability of 4-AcO-DMT, does the acetoxy group make it any more stable than psilocybin? Or more importantly, would 4-AcO-DMT be less stable than -DET, -DiPT etc?

I suppose as long as its stored in good conditions sealed/in a freezer it should keep for a long time.

Also I doubt anyone would have an answer really but i'm curious what other modifications to DMT could be made, anywhere on the molecule that would somehow allow it to make it through the mao enough to be active, but, ... uh.. not modify its activity TOO much? hehe.

I guess psilocin etc is the closest thing known to be most similar to DMT in effects and is able to not get eaten up by mao..

alpha-methyl-DMT would probably be active, but I wonder if the effects would be altered so much to where it.. wouldn't have that.. "DMT feel" :).

-- i've smoked bufotenin / 5-HO-DMT and it does have that wonderful "DMT feel" just makes me wonder what other possible tweaks could be done to make a molecule that retains that "DMT feel" :).
 
Alpha-N,N-trimethyltryptamine (alpha-N,N-TMT) is mentioned in TIHKAL, but the human pharmacology is unknown. However, looking at things like alpha-N-dimethyltryptamine I don't think it will be too appealing. With the alpha-alkylated tryptamine...anything other than a primary amine does not seem too psychedelic.

As far as 4-AcO-DMT, an chemist I used to do business with did make some. It said it was indeed much more stable than psilocybin, and was fully active when smoked. He did not say much on the effects, other than it was (for the most part) identical with a psilocybin experience.

As far as other modifications to the DMT molecule....once it is modified, it is no longer DMT! :) So I think it is kind of a muted point. On the other hand, alpha-vinyl-N,N-DMT looks reallu nice and fits into the LSD structure quite well. That may be an interesting thing to try.
 
On a 'blowing my own trumpet' sort of thing, I think the 4-vinyl DMT that I proposed in the 'Acid, dragonflies etc' thread would survive metabolism by MAO in the gut as substitution into the 4-position seems to prevent MAO getting 'a good hold' on the molecule to enable it to fit into the active site. Hopefully because of the fact that it doesn't contain the polar OH (or phosphate ester - psilocybin) goup, it would have better BBB penetration, while retaining psilocin's receptor affinity. It might just turn out to be very active because of the above (poss even just a few mg for fully active dose), but we'll not know until someone takes the plunge and whips some up for testing.

If that were the case, there'd be the possibilty of a series of highly active N,N-disubstituted tryptamines, all active at small doses. I'd bet 4-vinyl MiPT would be spectacular!

On the other hand, alpha-vinyl-N,N-DMT looks reallu nice and fits into the LSD structure quite well. That may be an interesting thing to try
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I'd bet that alpha-vinyl tryptamine would be a pretty good candidate for central activity - more like AMT than AET
 
Interesting discussion. I imagine that the vinyl group can be employed in TEA's and PEA's as irreversible ligands for their targeted receptor site. I selected amphetamine as a good test-bed on which to plonk a 4-vinyl moiety. Its mass (27) tends more towards methoxy (31) than fluorine (19), although it also has a lone pair of electrons to donate, something that a saturated ethyl group (29) is incapable of. I can dig a reference for Kozikowski making this group if desired. He uses the 4-bromophenyl ring as a precursor to it. Unfortunately, due to the laws in my country, this is an idea that is untenable for me to work with. However I have no business wanting to involve myself with amphetamine chemistry at any rate, although it could very well serve as an extension of 2cb chemistry for example. It is somewhat related to Limpet Chicken's idea to use an azide group (decomposes to a nitrene?) although I believe that the vinyl group is a more subtle choice of mutagen.
 
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All right you caught me out on that one but tryptamine has never really been a center of excellence for me. I have had some success with the Fischer indole synthesis but have never even tried any of the DMT's and AMT's.
 
Interesting..

So do you think 4-vinyl-DMT would have activity somewhat similar to psilocin or DMT "DMT-like or whatever, that natural ooey feeling"? If so uh, hehe i'd really love some :).
 
^ Not a clue, I'm only going on the idea that it's active because of the electron/charge distribution in terms of SAR criteria (for electrostatic binding to receptor). I'd be willing to bet a fair amount of money that it'd be active (and at relatively low doses by comparison to psilocin & DMT), but as to what it would be closest to in terms of effects is anybody's guess beyond 'psychedelic'.
 
vinyl-tryptamines and PEAs

I just made a short research, 4-vinyl tryptamine or derivatives gave no hits, but 5-vinyl tryptamine derivatives did:
Preparation of 5-alkenyl and 5-alkynyl indoles as 5-HT1D-like receptor agonists. Meng, Qingchang; Slassi, Abdelmalik; Edwards, Louise; Rakhit, Sumanas. (Allelix Biopharmaceuticals Inc., Can.). U.S. (1999), 11 pp. CODEN: USXXAM US 5856510 A 19990105 Patent written in English. Application: US 96-767322 19961216. Priority: . CAN 130:95475 AN 1999:34504 CAPLUS
The title compds. [I; R1 = H, (un)substituted aryl; A = CH:CH, C.tplbond.C; R2 = II-V (wherein R3, R4 = H, lower alkyl; one of R5 and R6 = H and the other = H, lower alkoxy, lower alkyl, OH; R7, R8 = H, lower alkyl; NR7R8 = 3-6 membered ring)], useful to treat indications where stimulation of the 5-HT1D-like receptor is implicated, such as migraine, were prepd. Thus, reaction of 5-bromo-3-[(N,N-dimethylamino)glyoxyl]-1H-indole with tributyl(vinyl)tin in the presence of tetrakis(triphenylphosphine) palladium(O) in DMF afforded 57% I [R1 = H; A = CH:CH; R2 = CH2CH2NMe2] which showed EC50 of 0.13 mM in vitro test on the rabbit isolated saphenous vein.

4-vinyl PEA is also described, but they make polymers (which could really be a problem with the handling of all those vinyl compounds) "Synthesis and polymerization of p-vinyl-b-phenylethylamine. Tahan, M.; Lender, N.; Zilkha, A. Dep. Org. Chem., Hebrew Univ., Jerusalem, Israel. Israel Journal of Chemistry (1972), 10(44), 835-9. "
Pharmacologically the 4-vinyl-PEA is in this article described as tranquillizing?!?

BTW: A friend of mine tested alpha, N,N-TMT and found it to be at 60 mg not psychedelic at all, rather relaxing. So, the alpha Me-group did not maintain the activity of DMT
 
Ok thanks for sharing this. I guess the vinyl group is made to look somewhat ridiculous when you take into account the synthetic side of the equation and the resultant compounds lack of stability. I take it then that the vinyl group being next-door to a phenyl ring does not lead to massive increases in its stability then? (ie resonace delocalization)
 
4-vinyl PEA is also described, but they make polymers (which could really be a problem with the handling of all those vinyl compounds)
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Why? polymers derived from polymerization of alkenes generally require an initiator to start the polymerization reaction (if I remember correctly, it's a free radical dependant mechanism). Without the initiator, alkenes (eg vinyl compounds) are fairly stable and only polymerize very slowly at room temp as long as they're not exposed to UV light; I've seen bottles of styrene (vinylbenzene) that have remained unchanged for years. If they were that unstable, samples of 5-methoxy DALT in peoples collections would be polymerizing before they could taste them
 
Theoretically it should be possible, but a quick research gave only very little hits concerning divinylamines at all.
An other thing that should be considered is that you will get an enamine instead of an amine, so the whole electronic situation (e.g. basicity) would be complete different.
 
morninggloryseed said:
So if 5-MeO-DALT can exist, why can't there be a divinyltryptamine?
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It's similar to the keto-enol tautomerization seen with alcohols (hydroxy group attached to carbon with a double bond). Alcohols like that mainly exist as ketones; with nitrogen/amines, (as EN21 pointed out) you get imines which tend to hydrolyse to a ketone and ammonia
 
BTW: A friend of mine tested alpha, N,N-TMT and found it to be at 60 mg not psychedelic at all, rather relaxing. So, the alpha Me-group did not maintain the activity of DMT
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Well a low dose of DMT is definitely very relaxing. Did he only try it the one time? I wonder what a 'psychedelic dose' of this is.
 
At 60 mg he tried it once (until now), but with 43 mg there were nearly the same effects, maybe comparable with a mild GHB buzz or a low dose of a opiate. Interestingly he therefore reported no lethargy at all, rather an activation to do the normal day work. This sounds controversy, because there was no body stimulation in him, but nevertheless an relaxed activation, -maybe there is an antidepressive effect?
When he tried it at 100 mg, I´ll make him to report again!
BTW: He isolated this compound as oxalate salt. He is a bit anxious about the oxalate which is harmful to the kidneys. Is this amount of toxicological relevance or not?
 
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morninggloryseed said:
Why would this occur with DVT, and not DALT?
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With DALT, the carbon of the allyl group attached to the side chain nitrogen doesn't have a double bond attached to it - that's what causes the instability. Move the double bond so it isn't attached to the carbon of the C-N bond and it'll behave pretty much like an alkyl group. Any C=C-N bond (or C=C-O bond for that matter) is sunject to keto-enol tautomerization to C-C=N (or C-C=O) and C=N bonds hydrolyse very easily to C=O bonds and NH3
 
At 60 mg he tried it once (until now), but with 43 mg there were nearly the same effects, maybe comparable with a mild GHB buzz or a low dose of a opiate. Interestingly he therefore reported no lethargy at all, rather an activation to do the normal day work. This sounds controversy, because there was no body stimulation in him, but nevertheless an relaxed activation, -maybe there is an antidepressive effect?
When he tried it at 100 mg, I´ll make him to report again!
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Heh.. sounds like DMT :). A lowish dose tends to 'relax' you / your body (and greatly increase coordination!), but sometimes it can feel like your mind is overclocked, like a CPU, able to rush through tasks/get things done way better than any amphetamine. ..without any noticeable "stimulation".

Can he relate the body buzz to low dose mushrooms? DMT and mushrooms do feel similar at low doses, relaxing.."fluidity" is common if you are aware of it or someone brings it up to you, sorta like deducting resources away from vision processing toward other brain processes (i believe thats why things can take on a more 'basic' geometric look on DMT, as opposed to DOC which seems to do the opposite at high doses).
 
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