Microsomal N- and C-oxidation of 4-substituted N-benzylanilines.
Using direct specific analytical techniques microsomal metabolism of N-benzyl-4-substituted anilines has been investigated and found to include both N- and C-oxidation. N-Debenzylation was observed with all substrates and species examined. N-Oxidation usually yielded aryl nitrones, although the N-hydroxy derivative of the 4-chloro-substituted substrate was identified in some species. This is the first direct evidence of microsomal N-hydroxylation of a secondary aniline. The metabolic formation of amides from these secondary amines was observed and is believed to be a novel class of metabolite for these substrates.
D000814:Aniline Compounds / Q000378:metabolism*; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D006224:Cricetinae; D006168:Guinea Pigs; D008297:Male; D008647:Mesocricetus; D051379:Mice; D008810:Mice, Inbred C57BL; D008862:Microsomes, Liver / Q000378:metabolism*; D010084:Oxidation-Reduction; D011817:Rabbits; D051381:Rats; D014052:Toluidines / Q000378:metabolism
D000814:Aniline Compounds; D014052:Toluidines; C047190:N-benzyl-4-chloroaniline; C047189:N-benzyl-4-toluidine; C028443:benzylaniline