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Synthesis of deuterium‐labelled chlorpromazine and chlorpromazine metabolites
Author(s) -
Craig J. Cymerman,
Gruenke L. D.,
Lee S.Y. Catherine
Publication year - 1978
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.2580150106
Subject(s) - chlorpromazine , chemistry , phenothiazine , sulfoxide , deuterium , tricyclic , side chain , stereochemistry , organic chemistry , pharmacology , medicine , physics , quantum mechanics , polymer
The synthesis of 2‐chloro‐10‐(3′‐dimethylaminopropyl)phenothiazine‐3′, 3′‐d 2 (Chlorpromazine‐d 2 ) and its four major metabolites (the mono‐ and didemethylated amines, chlorpromazine sulfoxide, and chlorpromazine N‐oxide), all containing the 3′, 3′‐d 2 label in > 95% isotopic purity, is described. Considerations leading to the optimum number and position of the labels are discussed, and the problem of coupling the aliphatic side‐chain to the tricyclic system is avoided by utilizing the readily available 2‐chloro‐10‐(2′‐cyanoethyl)phenothiazine as starting material, so that the carbon skeleton of the side‐chain is already in position before the isotope is introduced.