Synthesis of a deuterium‐labelled standard of bufotenine (5‐HO‐DMT)
Yu Yun Wang, Chinpiao Chen
Journal of Labelled Compounds and Radiopharmaceuticals October 1, 2007 DOI: 10.1002/jlcr.1459 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Synthetic chemistry paper Peer reviewed |
|---|---|
| Topics | DMT |
| Keywords | Deuterium Stereochemistry Radiochemistry Nuclear physics |
| Citations | 6 |
| Key points | Deuterium-labeled bufotenine was synthesized via the Batcho–Leimgruber strategy using lithium aluminum [2H4]-hydride to introduce four deuterium atoms. |
Abstract
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.
Citations in the library
Cites 6
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- Syntheses of Serotonin, N-Methylserotonin, Bufotenine, and Melatonin, and the First Total Synthesis of N-(Indol-3-yl)methyl-N-methyl-5-methoxytryptamine from Tryptamine through a Common Intermediate, 1-Hydroxytryptamine Heterocycles 1997
- Synthesis of deuterium labeled standards of 5‐methoxy‐N,N‐dimethyltryptamine (5‐Meo‐DMT) Journal of Labelled Compounds and Radiopharmaceuticals August 14, 2006
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