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Synthesis of a deuterium-labelled standard of bufotenine (5-HO-DMT)

✍ Scribed by Yu-Yun Wang; Chinpiao Chen

Publisher: John Wiley and Sons
Year: 2007
Tongue: French
Weight: 121 KB
Volume: 50
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.1459

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✦ Synopsis

Abstract

The Batcho–Leimgruber strategy was employed to synthesize 3‐(2‐dimethylamino‐[^2^H~4~]‐ethyl)‐1__H__‐indol‐5‐ol (bufotenine, 5‐HO‐DMT) (8) from commercial 3‐methyl‐4‐nitro‐phenol (1), benzyl bromide and N,N–dimethylformamide–dimethylacetal. Compound 4 was synthesized from compound 3 using the Batcho–Leimgruber strategy in the presence of Raney nickel and hydrazine hydrate. Compound 4 was treated with oxalyl chloride, dimethylamine and lithium aluminum [^2^H~4~]‐hydride to yield [2‐(5‐benzyloxy‐1__H__‐indol‐3‐yl)‐[^2^H~4~]‐ethyl]‐dimethyl‐amine (7). The benzyl ether in compound 7 was cleaved by hydrogenolysis to give bufotenine 8. Copyright © 2007 John Wiley & Sons, Ltd.

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