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Molecular Pharmacology, Vol 10, 634-639, Copyright © 1974 by the American Society for Pharmacology and Experimental Therapeutics

The Formation of Catechols by Consecutive Hydroxylations: A Study of the Microsomal Hydroxylation of Butamoxane

PATRICK J. MURPHY 1, JOHN R. BERNSTEIN 1, and ROBERT E. MCMAHON 1

1 The Lilly Research Laboratories, Indianapolis, Indiana 46206

The hydroxylation of butamoxane [2-(butylaminomethyl)-1, 4-benzodioxane] both in vivo and in vitro by an enzyme derived from rat liver yields a mixture of 6-hydroxybutamoxane and 7-hydroxybutamoxane in a ratio of approximately 2:1. In addition, the microsomal oxidation of butamoxane in vitro yields the catechol 6, 7-dihydroxybutamoxane. This same catechol is produced by the hydroxylation of either 6-hydroxybutamoxane or 7-hydroxybutamoxane. A series of 18O studies are described which support the concept that 6,7-dihydroxybutamoxane is formed via two consecutive hydroxylations rather than via a dihydrodiol or an endoperoxide.

Submitted on January 28, 1974






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