> I meant starting with 5-MeO-IAA not 5-Meo-T to form a,O-dimethylserotonin.
Yes, would work.
> Why the different proc anyways? (Me2NH compared to HCHO?)
Because if you start with a propanone, you need to add an amine (dimethylamine), if you start with an amine (tryptamine) you need an aldehyde.
> I mean, starting with 5-MeO-T is the formaldehyde / sodium cyanoborohydride
> used to introduce methyl groups onto the amine nitrogen?
Yes. But if you start with 5-MeO-indolylacetone (5-MeO-indolyl-2-propanone), you add dimethylamine.
> Does the first one also go for higher alkyls? e.g.
> Pr2NH + NaBH3CN to form alpha-Me-N,N-dipropyltryptamine?
Yes.
> What alternatives would there be to the use of NaBH3CN, since it's not that easy to acquire?
NaBH4 + acetic acid, NaBH4 + ZnCl2 (to get Zn(BH4)2 ), NaBH4 + Titanium isopropoxide, or perhaps Al/Hg (but I'm not sure if that works on tryptamines)
http://rhodium.lycaeum.org