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

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.