skr_nexus wrote:Not sure if such analogy should be drawn between phens and trypts. In trypts, that beta carbon is 1 carbon further away from the aromatic ring than in phens. And to me subtitutions seem to work differently in phens X trypts.
Trypts are psychedelic when the N is subtitutes at least once, ideally twice.
Phens are psychedelic when N is not subtituted, and when it is they turn into stimulants.
Obviously N-N- alkyl tryptamines are different from phenethylamines in general.
Tryptamines are only truly active when substituted twice at the amine, mono-alkylated tryptamines really aren't significant, and usually offer different activties. While in reverse, phenethylamines are only active as primary amines, and lose activity entirely at ht2a when N-methylated.
It's drawn this way because alpha-methyl tryptamines very much mirror the activity of the alpha-methyl phenethylamines
alpha methyl tryptamine, aMT, is an active psychedelic as a primary amine, and as well contributes significant MAOI and monoamine reuptake and releasing action that some of the phenethylamines show (in this case closer related to PMA and MDxx). On top of that aMT loses its serotonin agonism with N-alkylation, just like the phenethylamines do.
I don't make the rules, I agree its no reason to dismiss it entirely, I'm just offering an explanation why this remains unexplored. It just means chemists have better ideas they want to explore first.
Quote:In trypts, that beta carbon is 1 carbon further away from the aromatic ring than in phens.
you are thinking about this incorrectly.
You should treat the indole ring as an analogue as the phenyl ring, at least in this case. And this is how it substitutes in the receptor.
You shouldn't treat the C3 carbon of the indole as a 'beta' carbon analgoue of a phenethylamine. First of all it doesn't freely rotate, it just doesn't substitute. You have to think of these things dynamically. Two completely different species.
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