t-Butyl tryptamines?

[Cepheus]

Does such a thing exist? Would they have any pharmacological activity?

 

[its.euphoric]

i don't know

 

[boohigh]

i have seen on hyperlab synth and bioassya of n-tretbutyl tryptamine.
5 mg was an +1 for about 3 hours

 

[nuke]

t-Butyl amines are usually inhibitors of MAOI so it's probably active in either the mono-substituted or bi-substituted form.

The tertiary-butyl analogue, NTBT, is the remaining mono-substituted tryptamine that just might have psychotropic potential. In the 5 to 20 milligram area, there is a light-headed intoxication that is a totally pleasant buzz, but nothing more profound than that. Wouldn't it be fascination of it turned out that all of the mono-tryptamines (the NRT's) were GHB-like intoxicants, and totally devoid of psychedelic activity. That would be a true challenge to the SAR crowd. I was told many years ago that NTBT was extremely potent when smoked, but I never received any particulars, and I must leave that as a baseless rumor.
Two n-butyl groups gives the compound 4-HO-DBT, the theme of this recipe. It is not active at 20 milligrams, but I suspect that it will be so at a somewhat higher dose. There is the secondary-isomer, 4-hydroxy-N,N-di-sec-butyltryptamine (4-HO-DSBT, an oil that never crystallized) which should be an isomer of increased activity, but it has not been assayed. The iso-isomer (4-HO-DIBT, mp 152–154 °C) should be yet less active as the steric mess around that important nitrogen atom is much larger, and indeed it is not active at the same 20 milligram level. The tertiary isomer (4-HO-DTBT) has yet to be made and, as it is extremely crowded around that innocent nitrogen atom, it may be unmakable. The activity is unknown, as the compound itself is unknown.
How far can this argument be pushed? What about one of the N-alkyl groups having four carbons? Keeping the other N-alkyl group as the smallest and most simple methyl group, all four isomeric compounds are known. There is the n-butyl isomer (4-HO-MBT, an oil), the isobutyl isomer (4-HO-MIBT, mp 142–145 °C), the secondary butyl isomer (4-HO-MSBT, mp 138–140 °C) and the tertiary butyl isomer (4-HO-MTBT, mp 225–226 °C). Of these four materials only 4-HO-MTBT has been looked at as a possible psychedelic. Some 15 milligrams produced virtually no effects, maybe a hint of something in a few minutes and then nothing. Probably pure placebo.

 

[Sturnam]

^ I must say, it is somewhat frustrating when he talks about how drug X has a weird profile, mostly being that it's active but not psychedelic. Then he tells us how he synthed some analogs to see if one of the substituted tryptamines could have a completely different mode of action, but then never tested them. He's teasing us

I understand that he obviously has lots of ongoing projects, and only so much time to properly conduct trials, but it seems odd he would go so far as to purify a novel compound of interest, and then never touch it. Guess he was more interested in psychedelics than seeing the line where a psychedelic becomes a depressant/stimulant/empathogen. Any more educated guesses on the likelyhood of this being the case with some of his odd-ball creations?

BTW, we're talking about N-t-butyl right? Is there any thoughts/literature as to ring substituted t-butyl tryptamines? Are bulky ring substituents generally bad for tryptamine activity?

Lastly, anyone know why he called 5-MeO-TMT "Indapex"? All the searches turn up links back to his book and mention of it. No journal articles i found mentioning it. Did he just decide to give this one a name?

 

[hamhurricane]

^^^
off topic but i wondered about the name indapex as well, he probably thought it had potential as a pharmaceutical, alpha-ethyl-DOM had the proposed pharmaceutical name dimoxamine

 

[planckunit]

^^^
off topic but i wondered about the name indapex as well, he probably thought it had potential as a pharmaceutical, alpha-ethyl-DOM had the proposed pharmaceutical name dimoxamine

don't you mean alpha-ethyl-2c-d because alpha-ethyl-dom would be a really weird phentermine type compound. Would be interested in the activity if it is actually a-et-dom and not ariadne.

 

[Hammilton]

I've taken a few of these N-mono alkyl tryptamines, and I know I've talked about them here, either as me or as "ham-milton" might want to search. Were interesting.