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Phenethylamines Psychedelic phenethylamine derivatives containing a cyclic amine function?

necropolis

necropolis

Bluelighter
Joined
Apr 10, 2020
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Psychedelic phenmetrazine analogues, anyone? I was thinking about this the other day.

A couple of examples might be 3-methyl-[2-(2,5-dimethoxy-4-methylphenyl)]morpholine and 3-methyl-[2-(2,5-dimethoxy-4-chlorophenyl)]morpholine. I wonder if any such compounds might show appreciable affinity for the 5-HT2A receptor, in general maintaining the conventional substitution pattern of a halogen, methyl, or sulfur substituent at the 4-position of the phenyl ring with a methoxy at the 2- and 5- positions. At the other end of the compound, other cyclic amines (e.g. piperidine, pyrrolidine and others) could be explored. No way of knowing short of synthesis and testing (or docking studies at the very least), whether any such hypothetical substances would maintain the right pharmacology to be active as psychedelics. It'd be interesting to find out though. To me anyway. Any thoughts/comments/criticisms are much appreciated.
 
2C-B-Morpholine seems to be pretty weak, referencing https://doi.org/10.1021/jm040082s. Secondary amines on phenethylamines generally decrease 5-HT2a receptor affinity, see N-Methyl-DOB for instance. DOB-Morpholine, like you're suggesting, could be interesting and active in at doses in tens of milligrams. However it doesn't appear to exist in literature.
 
Funny, I was just thinking of these the other day and posted to the name-a-chemical thread ...

SKL said:
3-methyl-2-(2%2C5-dimethoxy-4-methylphenyl)morpholine.png


ANTIGONE.

Substitute the methyl group at the 4 position and you'll have JOCASTA (bromine), ISMENE (iodine, with apologies to @Ismene2), EURYDICE (ethyl), etc.
Click to expand...

This thread might do better in ADD.
 
The closest that I see, at least as far as Shulgin is concerned, are entries# 56 and 104 in PIHKAL, however, while the original question pertains to phenethylamines, in TIHKAL there are 3 pyrrolidines listed: #'s 24, 43 and 52. Granted being tryptamines, I don't know that anything useful can be inferred what so ever. I mean none of the tested tryptamines with a methylenedioxy substitution seemed to even whisper that magic was around the corner. That said, none of them look particularly promising. Honestly, I feel like something rare like MMDA-3a or many of the 3C phenethylamines in their optically pure form would be more worth investigating.
 
anything with a secondary or tertiary amine function destroys psychedelic activity, at least when it comes to the pea's.
 
Well my statement was based on Alexander shulgins saying in pihkal. Meanwhile there are the secondary nbomes and One cyclic piperidine compound on wiki by nichols group with activity. I don’t know anything on the activity on anhalinine.
 
izo said:
Well my statement was based on Alexander shulgins saying in pihkal. Meanwhile there are the secondary nbomes and One cyclic piperidine compound on wiki by nichols group with activity. I don’t know anything on the activity on anhalinine.
Click to expand...
Would be an interesting experiment for sure. Wikipedia states that one can make hydrastinine from homarylamine by reacting it with formaldehyde. Maybe you could do the same thing with mescaline and cleave off the OH-group with NaBH4 or sth.?
 
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