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Synthesis of psilocin labelled with 14 C and 3 H
Author(s) -
Poon Grace,
Chui YunCheung,
Law Francis C. P.
Publication year - 1986
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580230207
Subject(s) - chemistry , tryptamine , lithium (medication) , sodium thiosulfate , acetic acid , stereochemistry , organic chemistry , medicine , biochemistry , endocrinology
14 C‐ and 3 H‐Labelled psilocin (4‐hydroxy‐N,N‐dimethyl‐tryptamine), the principal, active agent of hallucinogenic mushrooms, was synthesized from 2‐methyl‐3‐nitrophenol via 4‐benzyloxyindole. 14 C‐Labelled potassium cyanide was reacted with 4‐benzyloxygramine (obtained from 4‐benzyloxyindole) to give 14 C‐4‐benzyloxy‐3‐indole acetic acid, an intermediate for 14 C‐psilocin synthesis. 3 H‐Labelled lithium aluminium hydride was used to react with 4‐benzyloxy‐3‐indole‐N,N‐dimethyl‐glyoxylamide (obtained from 4‐benzyloxyindole) to give 3 H‐4‐benzyloxy‐psilocin which was debenzylated to form 3 H‐psilocin.