Syntheses of N-Alkyl-N-(ω-carboxyalkyl) nitrosamines Related to N-Butyl-N-(3-carboxypropyl) nitrosamine, Principal Urinary Metabolite of a Potent Bladder Carcinogen N-Butyl-N-(4-hydroxybutyl) nitrosamine

Abstract

Fourteen N-alkyl-N-(ω-carboxyalkyl) nitrosamines related to N-butyl-N-(3-carboxypropyl) nitrosamine, principal urinary metabolite of a potent bladder carcinogen N-butyl-N-(4-hydroxybutyl) nitrosamine, were prepared for the purpose of mainly characterizing urinary metabolites and in part testing their carcinogenic effects in rats. They were N-alkyl-N-(3-carboxypropyl) nitrosamines, N-alkyl-N-(2-carboxyethyl) nitrosamines, and N-alkyl-N-(carboxymethyl) nitrosamines. They were mostly prepared by the permanganate oxidation of the corresponding N-alkyl-N-(ω-hydroxyalkyl) nitrosamines.