A deuterium-labeled version of the psychedelic compound N,N-dimethyltryptamine (DMT) was synthesized. Starting from a commercially available nitroaromatic compound, the 5-methoxy group was labeled with three deuterium atoms using deuterated iodomethane. The synthesis followed the Batcho-Leimgruber indole synthesis, then introduced the side chain via oxalyl chloride and dimethylamine, and finally reduced the amide with lithium aluminum hydride to give 5-[2H3]-methoxy-N,N-dimethyltryptamine.
A method for synthesizing deuterium-labeled versions of two psychoactive amphetamine derivatives, DOM and MMDA, is described. The labeled compounds are intended for use as internal standards in gas chromatography–mass spectrometry (GC–MS) assays to improve measurement accuracy.
A synthetic route to deuterium-labeled bufotenine (5-HO-DMT) was developed using the Batcho–Leimgruber strategy. Starting from commercial 3-methyl-4-nitrophenol, the synthesis proceeded through benzyl protection and reaction with N,N-dimethylformamide–dimethylacetal. Reduction with Raney nickel and hydrazine hydrate gave an indole intermediate, which was then treated with oxalyl chloride, dimethylamine, and lithium aluminum [2H4]-hydride to introduce four deuterium atoms. Final hydrogenolysis removed the benzyl ether, yielding the labeled bufotenine. This method enables the preparation of a deuterated analog of the psychoactive compound for use in tracer studies or metabolic investigations.