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Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines

✍ Scribed by Simon D. Brandt; Sri Subha Tirunarayanapuram; Sally Freeman; Nicola Dempster; Steven A. Barker; Paul F. Daley; Nicholas V. Cozzi; Cláudia P. B. Martins

Publisher: John Wiley and Sons
Year: 2008
Tongue: French
Weight: 166 KB
Volume: 51
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.1557

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✦ Synopsis

Abstract

A large number of N,N‐dialkylated tryptamines are known to induce psychoactive effects in humans. This has resulted in their increased attention within clinical and forensic communities. Deuterated tryptamines are ideal for use as internal standards during MS bioanalysis or of use in biochemical NMR studies. The present study reports on a microwave‐enhanced synthesis of 22 N,N‐dialkylated‐[α,α,β,β‐d4]‐tryptamines via the reduction with lithium aluminium deuteride of glyoxalylamide precursors obtained by the procedure of Speeter and Anthony. Syntheses were carried out using a single‐mode system under elevated pressure conditions where anhydrous tetrahydrofuran was used as the solvent at 150°C. Good yields were obtained within 5 min. Copyright © 2008 John Wiley & Sons, Ltd.

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