Primary aliphatic amine metabolism: the formation of a stable imine metabolite.

The possible role of hydroxylamine and imine intermediates in the metabolism of amphetamine and related primary amines is discussed. The inherent instability of imines, has hitherto precluded the recognition of these compounds as metabolites of primary amines. During studies on the metabolism of o-methylbenzhydrylamine using washed hepatic microsomes from a number of mammalian species, the formation of o-methylbenzophenoneimine as a metabolite was observed. This metabolite was identified by preparative thin layer chromatography followed by gas-chromatography combined with mass spectrometry.