Reactions of chlorpromazine cation radical with physiologically occurring nucleophiles

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Abstract
The reactions between chlorpromazine cation radical and a variety of physiologically occurring nucleophiles, which involve formation of a covalent, yet reversible bond, were examined. This reaction did not involve disproportionation of the radical but, rather, direct reaction between radical and nucleophile. The resulting adduct reacted to form chlorpromazine sulfoxide or hydroxylated derivatives and the original nucleophile is regenerated. The products and kinetics of the reaction depended strongly on the identity of the nucleophile, with the sulfhydryl group being the fastest and water being the slowest of the nucleophiles studied. The likely involvement of these reactions in the metabolism of chlorpromazine was discussed. The radical/nucleophile interaction might be a reasonable model reaction for the effects of chlorpromazine radical on neuronal enzymes and receptor sites.

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