Regarding reduction with acetone.
It might be possible. In O-Chem, experimental results always trump theory. As I recall, Heinzelman was able to produce an N,N-Di-(phenylisopropyl)-methylamine, just by reducing a methamphetamine in the presence of a phenyl2propanone.
J. Am. Chem. soc. 75, 921 (1953)
(
https://www.thevespiary.org/rhodium/Rhodium/pdf/2-meo-methamphetamine.pdf)
You should have this paper, regardless. It is quite interesting.
He performed his reduction using H2/Pt, which might work for you, or might not. Some data suggests there could be competing reactions.
With some tryptamine, a little acetone, some methanol, and a little Pt/H2....or Al/Hg, you could know something the rest of us don't...in just a few hours.
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