Methyl AMT/AET

[cannibalsnail]

In Amphetamine compounds (Amp/MDA) adding a methyl group to the Nitrogen group increases affinity for Serotonin creating a more euphoric version.

Doing this to AMT (http://www.erowid.org/library/books_online/tihkal/tihkal08.shtml) didn't appear to have the same effect. Any clue why? Is it possible Shulgin failed the synthesis?

In addition, has this been tried with AET which is already a more entactogenic/euphoric version of AMT?

Proposed substitutions:

 

[flaming]

Where are you seeing N,a-DMT and N-methyl-a-ethyltryptamine mentioned in your linked TiHKAL article? I find mentions of 4-HO-aMT, 5-HO-AMT, 5-MeO-aMT (a,O-DMS), 1,a-DMT, a,a-DMT, and 4,a-DMT, but I don't seen any mention of N,a-DMT or N-methyl-a-ethyltriptamine on either that page or TiHKAL's aET entry (although the aET entry does contain a very interesting discourse on analogue laws).

 

[cannibalsnail]

Corrected the link.

 

[flaming]

Don't take this as universal but it's speculated by some (using docking simulation at various 5HT receptors) that the non-indole nitrogen in tryptamines binds to the same parts of the 5HT2A/C receptors as the nitrogen in various potent phenethylamines such like DOI and the NBOMe series. This would explain the differing actions of converting the hanging primary amine into a secondary amine via a methyl group.