Electrochemical oxidation of hydroxylated phenothiazine and imipramine derivatives

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Abstract
The electrochemical oxidations of several hydroxylated derivatives of promazine, chlorpromazine, imipramine, and 3-chloroimipramine were examined and compared. Oxidation of the monohydroxyphenothiazine derivatives leads to both dihydroxy species and substituted benzoquinones, while oxidation of hydroxylated imipramines leads to only the corresponding benzoquinones. The oxidation potentials of 17 tricyclic psychoactive drugs and metabolites were tabulated and compared. The potential importance of these results to drug activity and side effects is discussed.