I have a hunch that certain N-alkyl melatonins (amyl, the butyl isomers, propyl, maybe even ethyl) might be worth exploring as psychedelics. It's likely that I'm wrong, but it's a nagging hunch been at me for a little while; they haven't been mentioned as far as I know, except Shulgin's mention that N-ethyl-melatonin doesn't hydrolyse easily. As for synthesis, I quickly found a few methods for alkylating amides, the old style reaction with sodium metal seems the wrong way to go, and the newfangled microwave method with PTC seems the most reasonable way ( http://www.mdpi.org/molecules/papers/41100333.pdf ), refluxing with PTC/toluene/RX has also been mentioned. The method cited uses TBAB, but I wonder if other quaternaries might be decent replacements? It would be rather nice if benzalkonium chloride for instance works here. Also, will simple sublimation do in place of a Kugelrohr? This seems a rather simple experiment, but one which I currently don't have the means to perform, I'm working on that, I certainly intend to experiment a little in the future. If any of you would be as kind as to offer tips or suggestions or guidance (or dissuasion?) etc. it would be much appreciated.

Decarboxylation? Melatonin is not a carboxylic acid.

I think the suggestion is promising, though I don't know if the amides would be anything more than prodrugs.