I looked, but did not find.
In one version of tryptamine synthesis, oxalyl chloride is condensed with indole, then the stuff alkylates some amine to give this (I don't know what it's called)
Molecule: (https://www.the-hive.ws/forum/faq.pl?Cat=#applet)
intermediate ("c1nc2ccccc2c1C(=O)C(=O)N(C)C")
Which is then reduced with LiAlH4, usually. Every reaction on beilstein does this. Maybee some bee has used the clemenson reduction also, I do not know.
What I would like to know is whether a Wolff-Kishner reaction would remove those carbonyls, or reaction conditions would destroy the tryptamine. (Pictet-Spengler, Lili? 8) Or something?)
I guess if acidic conditions cause that, it would be a strike against the Clemenson. But Wolff-Kishner is basic. Any threads here on this matter already? UTFSE again?
I guess there are possibilities for the amide to come out of the Clemmensen more or less intact, but this reduction is known to sometimes cause impredictable results with substrates that are more than just plain ketones (have other functions as well). Besides I don't even know if it works for beta-keto-amides. The indole group can also bee cause for many unpredictabilities (just think of the NaBH4 reduction of 3-acethyl-indoles). And then, what should be done with the amide group? Just don't say LiAlH4 please.
Edit: The best thing to try out would bee a NaBH4 reduction of both the amide and the keto group like in https://www.thevespiary.org/rhodium/Rhodium/clandestine/dmt/index.html (https://www.thevespiary.org/rhodium/Rhodium/clandestine/dmt/index.html)
but in the presence of a catalyst that enables the borohydride to reduce amides (maybe NiCl2?).