Neptune and McCreery

The electrochemical (and chemical and enzymic) oxidation of 7-hydroxychlorpromazine leads to the eventual formation of 7,8-dioxochlor-promazine which, according to the mechanism proposed by Neptune and McCreery, " proceeds through a trihydroxylated intermediate (VI, Figure 10). It has been suggested " that the oxidized form of the latter compound (i.e., VII, Figure 10) could react with neuromembrane proteins, particularly at thiol sites, in the same way described for the p-quinone of 6-hydroxy-dopamine (see p. 143) and hence cause some neurophysiological effect. 

It has been noted in earlier discussion (Figures 10 and 11) that quinone-imine intermediates are formed on electrochemial oxidation of hydroxylated chlorpromazine derivatives. Neptune and McCreery have concluded that since hydroxylated chlorpromazine metabolites are important in the beneficial and side effects of chlorpromazine then intermediates such as quinoneimines may be important in vivo. 

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