new stimulant skeleton?

[anj0vis]

I posted about a new PhD thesis on the Drugnews board:
http://ethesis.helsinki.fi/julkaisut.../vk/pihlainen/ liquidch.pdf

in addition to interesting development in CG/MS technique, it also shows a few very interesting analogues of common drugs. See pages 34-35. It shows formulas for numerous known drugs and numerous analogues of known drugs. See compound no. 4, it looks interesting. Chemical name would around alpha-methyl-MDMA or similar (correct me those who know better).
This led me to the idea to substitute amino group into the place of alpha-methyl group in amphetamine compounds. Is this alpha-amino-phenethylamine (AAPEA?) ever been tested or researched anywhere? Would the 4-x-2,5-dimethoxy-AAPEA show psychedelic activity between 2c-x series and DO-x series? The amino group would be a bit smaller than methyl group (N has electronegativity of 3.0, while C has 2.5) and hydrogen donation possibility would thus be smaller than in amphetamine skeleton. But if I remember correctly, it was not much of an issue in the alpha-position in PEA skeleton (according to the 5ht2 receptor model), so it might not be an issue. Would the geometric configuration of this alpha-amino group be a problem for activity? Edited by: nanobrain

[nanobrain]

anj0vis thanks, bitchin reading, will make for some good times. topic may be better suited in phen chemistry? let me know.

[anj0vis]

I wondered about the choice of board myself, but I have not a hint about how to synthesize these, so I chose this. Feel free to move this to phen chemistry side if you think it fits better.

Continuing along the same line, has there been tests on OH group substitutions into alpha-position? How about halogens, like Bromo, Iodo or similar? I'd guess that amino group would work best, but.. it is just a guess.

[gn2osis]

Great in theory but two amine groups attached to adjacent carbons
probably wouldn't be stable. One of them would pop off and you'd
ultimately be left with an aldehyde. Same problem with
bromine. You'd want something that can't be a good leaving group
if subjected to nucleophilic attack. What about keeping that
alpha-methyl group there and sticking a fluorine or two on it?



(edited for dumb factual error on my part)

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Edited by: gn2osis

[anj0vis]

ok, that explains.. thank you. How about the OH group?

[gn2osis]

^ Same problem<!--
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[anj0vis]

that is a pity, a new substitution pattern position would have multiplied the number of possible options, but..