Synthesis of a deuterium‐labelled standard of bufotenine (5‐HO‐DMT)
Journal of Labelled Compounds and Radiopharmaceuticals October 1, 2007 Yu Yun Wang, Chinpiao Chen 6 citations
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.