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4-Br-aMT

C

Cepheus

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Purely hypothetical; could such a thing exist and what effects / toxicity would be expected.

I was aiming for a tryptamine analogue of dob.
 
Surely it could be made. What it would do, though, is anyone's guess. I don't know if any ring-halogenated tryptamines have been prepared.
 
A tryptamine analogue of DOB would require the halogen to be on the fifth or more preferably sixth position. The fourth (fifth more so) position on tryptamine and the ringed nitrogen are comparable to the two, five para-substituted methoxyl groups on phenethylamine and amphetamine psychedelics. In TiHKAL, Shulgin mentions a similar compound the suggested; "5-Bromo-DMT and 5,6-dibromo-DMT are found in the sponges Smenospongia auria and S. echina resp. I have no idea if they are active by smoking".

For both tryptamine and phenethylamine it's believed they lock the molecule into position through hydrogen bonding, which bromine can't participate in, at two serine residues inside the 5-HT2A receptor. As a result of this, and other interactions, the amine tail is in a preferred position for hydrogen bonding at a asparagine residue which seems to be a crucial but not sole contributor for activating the receptor. This explains why phenethylamine and amphetamine are not psychedelic - they cannot "lock into position" of this receptor.

Please excuse any inaccuracies.
 
This is how i understand the substitution patterns on tryptamines and phenethylamines (and their overlaps)

2n7dyrq.jpg
 
I think you have it upside down Wungchow. The latest I saw it proposed was "Towards a biophysical understanding of hallucinogen action" D.E. Nichols, M.A. Braden, etc (see image below). The N-benzyl derivatives (25I-NBMeO, etc.) also follow the phenethylamine docking, but a bit adjusted for the tail to accommodate pi-pi interaction with the phenylalanine residue (Phe6.51(339)).

j5e6bq.jpg
 
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^Thanks for the informative diagram!

I was under the impression 5-MeO DMT docking would look more like this...

o0p0tt.png


That way the extended aromatic indole system isn't protruding into a hydrophillic pocket...
 
Also, when we consider the case of 4-HO-DMT...

v3hsea.jpg


Note that in Nichols' model, the 4-HO group is kind of isolated...

Maybe I'll shoot him an email and see what he thinks. When was this published? (I'm off campus so i can't get the full article)
 
Wungchow check your inbox.

The ethylamine is seems too severely twisted in your version in my opinion. Also I don't think the hydroxyl group be would able to hydrogen bond at that distance if the position two methoxyl on phenethylamine is unlikely/unconfirmed. It might be isolated but it could help contribute to to pharmacokinetics instead of docking. I can't speculate on that, it will be sometime until I can take pharmacology courses.

This is was published May 2007. Dr Nichols mentioned at the MAPS neuroworkshop that him and his team are working on a suspected "active metabolite" of LSD which has an interesting theory behind it's reasoning I won't spoil. I believe that's going to be July-ish this year, if I recall correctly. Very exciting. Either way, probably no more tryptamines from his side.
 
it will probly be like 4-methyl r 4-methoxy-aMT, other than that I cant say. like how 5-br-DMT is like 5meo
 
I know in the animal studies regarding 5-Br-DMT it appeared to cause a sedative effect, but who knows if something more interesting was going on mentally... 5,6 dibromo DMT appeared to have an anti-depressant effect, but again, at larger doses, or in different species (these studies were done with rats) who knows what subjective effects occur. Also, given that aMT is an anti-depressant, the compound the OP suggested may well be effective in that regard, but that's pure speculation on my part.
 
(zonk) said:
it will probly be like 4-methyl r 4-methoxy-aMT, other than that I cant say. like how 5-br-DMT is like 5meo
Click to expand...

and how exactly is 5-Br-DMT for those who have not yey had the access to it. 4M-4Meo-aMT is a real thing.
? I'd rearch lil harder but I never really did care much for AMTor 5-MEO-AMT.

I know they have a few very vocal proponents, and I do not wish to detract from them. so cheers !
 
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