Studies in detoxication. 24. The metabolism of p-phenetidine (p-ethoxyaniline) with some observations on the anisidines (methoxyanilines)

Abstract

About 30% of the p-phenetidine fed was excreted as ethereal sulfates. The main phenol in the sulfate fraction was 2-hydroxy-4-ethoxyaniline. A considerable amt. of glucuronide was excreted which appears to be largely labile glucuronide. p-Acetamidophenylglucuronide was also isolated from the urine. This substance was obtained in 6% yields, but may occur in the urine to the extent of 20% or more. A.p-toluidineammonium glucuronate complex was isolated from p-phenetidine, o-, m-and p-anisidine urines. The p-toluidine complexes of ammonium glucuronate and galacturonate were synthesized.