According to the same thread you referenced to, quaternary tryptammonium salts gotten from MeI alkylation can be reconverted to N,N-dimethyltryptamines with ethanolamine.
So: condense indolylaldehyde and nitromethane, reduce the nitrostyrene double bond with aequ. NaBH
4, then aminate via nickel borate/hydrazine, triacetoxyborohydride,cyanoborohydride or other selective reducing agent to get tryptamine (or do both at once with LiAlH
4), hope for not having touched the indole nitrogen
![Wink ;)](https://thevespiary.org/talk/Smileys/default/wink.gif)
, and do whatever you like with it (there are many alkylhalides - and what about alpha-ethyl-(N,N-dimethyl)tryptamine btw? Think I gonna consult TiHKAL...) Nice if it would work.
(or, if you want N,N-DMT: simply alkylate with HCHO/NaBH
3CN - that is, unless Lilienthal is right with his cyclization theory about tetrahydro-betacarbolines...)
indole_amine