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.
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