Synthesis of O‐Acetyl‐N (4‐biphenylyl)hydroxylamine (“NAcetoxy‐4‐aminobiphenyl”), an Ultimate Metabolite of Carcinogenic 4‐Aminobiphenyl, and Its Reaction with Deoxyguanosine

The carcinogenicity of aromatic amines has been known since 1895. It has now been possible for the first time to convert the hydroxylamine derivative generated from 4-aminobiphenyl 1 into the crystalline title compound 2 in vitro. 2 reacts with deoxyguanosine to give the same “adducts” which, e.g., are also obtained when 1 is administered to dogs and the DNA is subsequently cleaved enzymatically (Aryl = 4-biphenylyl).