Abstract
The synthesis of 2-chloro-10-(3′-dimethylaminopropyl)phenothiazine-3′, 3′-d2 (Chlorpromazine-d2) and its four major metabolites (the mono- and didemethylated amines, chlorpromazine sulfoxide, and chlorpromazine N-oxide), all containing the 3′, 3′-d2 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.
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