Studies in detoxication. 58. The metabolism of aliphatic alcohols. The glucuronic acid conjugation of chlorinated and some unsaturated alcohols

Abstract

The glucuronic acid conjugation of a number of chlorinated and other aliphatic alcohols was studied in the rabbit, and the glucosiduronic acids were isolated as triacetyl methyl esters in each case. Conjugation with glucuronic acid becomes a significant metabolic path when 2 or more chlorine atoms are present on the carbon atom next to that carrying the hydroxyl group. Thus 2-chloroethanol is not conjugated, whereas 2,2-di- and 2,2,2-tri-chloroethanols are highly conjugated (more than 50%). It is suggested that chlorine substitution retards oxidation of the alcohol and thereby increases its narcotic activity. 3-Methylpentan-3-ol, 3-methylpent-l-en-3-ol and 3-methylpent-1-yn-3-ol are conjugated with glucuronic acid to about the same extent (50%). Diethylamino-ethanol does not cause excretion of extra glucuronic acid in rabbits.