Novel tryptamines….

[Rabidreject]

Okay so I’m sure some people are aware iv been making,n-DMT and other tryptamines using reductive amination at cold temps…
so I’m wondering, seeing as there are so many things based on the 2,5-dimethoxybenzaldehyde, I’m curious what if you were to use that as the source of aldehyde in this reaction?
i also wondered the same of cyclohexanone but as a ketone of course…

so with the former would you hypothetically obtain something like 2,5-dimethoxy-4-methyltryptamine? Would this be active?

how about n-cyclohexyltryptamine?

are any of these likely to be active at all? I need to try and do more general reading on structure activity relationships, which is my plan over the weekend on a couple subjects, this being one of them….

I guess it just got me thinking….

 

[Rabidreject]

Am I being mental? I’m surprised no one has chimed in here….are most chemists here doing am-her and stuff?

 

[DavidNichols]

Piperidine derivatives of tryptamines serve no purpose. Loss of potency and no distinctive effects.

Structural pharmacology and therapeutic potential of 5-methoxytryptamines - PMC

Psychedelic substances such as lysergic acid diethylamide (LSD) and psilocybin show potential for the treatment of various neuropsychiatric disorders1–3. These compounds are thought to mediate their hallucinogenic and therapeutic effects through the ...

www.ncbi.nlm.nih.gov

You mismatch tryptamine nomenclature and phenethylamine.

Tryptamine - Wikipedia

en.wikipedia.org

 

[Rabidreject]

Yeah apologies about this. I wrote this a while ago before I’d actually started looking into PEA chemistry.

Iv definitely heard of 5-MEO-pyrolidinetryptamine and I believe a fluorinated one as well that came out the Nichols lab. I mean, it doesn’t sound pleasant really but is an interesting one that I believe someone ended up being found naked on campus after ingesting some of the 5-Meo-pyr-tryptamine, at the Nichols lab.
They really have made A LOT of interesting stuff there - was it not also Nichols who came up with the whole idea and chemistry for a lot of the n-benzylphenethylamine’s as well?

 

[HerrHaber]

Well I made several that have superpotent radiolabeled ligand displacement behavior but this is in between my own self that didn't have enough so far (too much would be scary) and independently by the Prof. Nichols the one from the picture above and a handful of people inside a research department of a university or so it was back then...

 

[DavidNichols]

Would it be okay for you to provide any anonymous firsthand insights on cyclobutane-based and azetidine-substitute ones?

 

[HerrHaber]

You mean like LSZ? or otherwise I already see the molecules I imagine you meant 2-benzyl substituted azetidines would be potentially active... I personally love aziridines but know they're not healthy. Thank's for the inspiration, is this hot now or?

P.S. I wonder if by any chance in the method of synthesis for MDMA from Bromo-3,4-benzodioxole and propylene oxide would have the latter replaced with 1,2-dimethylaziridine I speculate that final product could be obtained in a one-pot reaction. The aziridine I am referring to could not be found.

 

[HerrHaber]

WPS 365

eu.docworkspace.com

 

[HerrHaber]

 

[DavidNichols]

I meant TCB-2 and ZCB. I do not recommend to administrate neither 2-benzyl, nor your novel ZADAM. But if you want to poison some rabbits with inferior chemicals I have a better and more bizarre version of benzodioxole variant.

 

[HerrHaber]

Thank you for bringing TCB2 and ZCB back in my field of view... my sketches were only making use of the azetidine moiety in a less calculated manner. I found nothing about ZADAM and ZCB I have yet to figure out how it's synthesis is approached. The benzodioxole thing was just an example of making use of aziridines to obtain PEA's from halogenated aryls and I have no clue wether it work's or not (propylene oxide does for MDMA synthesis).