Synthesis of deuterium labeled standards of 5‐methoxy‐N,N‐dimethyltryptamine (5‐Meo‐DMT)
Journal of Labelled Compounds and Radiopharmaceuticals August 14, 2006 DOI: 10.1002/jlcr.1109 (opens in new tab) via OpenAlex
Summary
AI-generated from the abstractA 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.
Study at a glance
| Characteristics | Synthesis paper Peer reviewed |
|---|---|
| Keywords | Dimethylamine Oxalyl chloride Yield engineering Lithium medication Indole test |
| Citations | 14 |
| Key finding | 5-[2H3]-methoxy-N,N-dimethyltryptamine was synthesized from 5-hydroxy-2-nitrotoluene and CD3I via the Batcho-Leimgruber strategy. |
Abstract
Abstract The Batcho‐Leimgruber strategy was employed to synthesize 5‐[ 2 H 3 ]‐methoxy‐1 H ‐indole 4 from commercially available 5‐hydroxy‐2‐nitrotoluene 1 and CD 3 I. Compound 4 was treated with oxalyl chloride, dimethylamine and lithium aluminum hydride to yield 5‐[ 2 H 3 ]‐methoxy‐ N , N ‐dimethyltryptamine 6 . Copyright © 2006 John Wiley & Sons, Ltd.