Metabolic oxidation of aralkyl oximes to nitro compounds by fortified 9000g liver supernatants from various species.
Incubation of 'amphetamine oxime' (IIa, anti-benzyl methyl ketoxime) with fortified rabbit liver 9000 g supernatants gave the nitro compound (Ie) and the beta-hydroxylated oxime (IIc) in addition to the previously reported ketone (IIb) and alcohol (Ic) metabolites. Formation of the products was cofactor dependent. The nitro compound was also formed using mouse, hamster and guinea-pig 9000 g liver supernatants and to a minor extent by rat liver. The oximes of 2-phenethylamine (IIe) and norfenfluramine (IIg) were also metabolized to the corresponding nitro compounds, ketones and alcohols with rabbit 9000 g liver supernatants; however, no nitro compound (IIIb) was detected after the incubation of 'mexiletine oxime' (IVa). The metabolic products were identified and characterized by g.l.c., t.l.c. and g.l.c. linked mass spectrometry by comparison with synthetic materials.
D000662:Amphetamines / Q000378:metabolism; D000818:Animals; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D006224:Cricetinae; D006168:Guinea Pigs; D066298:In Vitro Techniques; D008099:Liver / Q000378:metabolism* / Q000648:ultrastructure; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D008647:Mesocricetus; D051379:Mice; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000378:metabolism*; D010084:Oxidation-Reduction; D010091:Oximes / Q000378:metabolism*; D011817:Rabbits; D051381:Rats; D013045:Species Specificity
D000662:Amphetamines; D009574:Nitro Compounds; D010091:Oximes