Phencyclidine metabolism in vitro. The formation of a carbinolamine and its metabolites by rabbit liver preparations.
Four products of the in vitro oxidative metabolism of the piperidine ring of phencyclidine, 5-(1-phenylcyclohexylamino)valeraldehyde, V; N-(1-phenylcyclohexyl)-1,2,3,4-tetrahydropyridine, VIII; 5-(1-phenylcyclohexylamino)valeric acid, VII; and 1-phenylcyclohexylamine, IX, have been identified following derivatization, by GC/MS with stable isotope labeling and/or synthesis. The enamine, VIII, may be a work-up elimination product of a carbinolamine, alpha-hydroxy-N-(1-phenylcyclohexyl)piperidine, IV. The formation of all metabolites requires microsomal enzymes, but VII and the previously described N-(5-hydroxypentyl)-1-phenylcyclohexylamine, VI, also require soluble enzymes. Quantitative or semiquantitative data show that VI and VIII appear and disappear with time, whereas VII seems to be a terminal metabolite.
D000818:Animals; D003514:Cyclohexylamines / Q000378:metabolism; D008099:Liver / Q000378:metabolism*; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism; D008954:Models, Biological; D010084:Oxidation-Reduction; D010622:Phencyclidine / Q000031:analogs & derivatives* / Q000378:metabolism*; D011817:Rabbits; D013347:Subcellular Fractions / Q000378:metabolism
D003514:Cyclohexylamines; C037321:5-(1-phenylcyclohexylamine valeraldehyde); C031090:5-(N-(1'-phenylcyclohexyl)amino)pentanoic acid; C037323:2-hydroxy-N-(1-phenylcyclohexyl)piperidine; C037322:N-(1-phenylcyclohexyl)-1,2,3,4-tetrahydropyridine; C037320:1-phenylcyclohexylamine; D010622:Phencyclidine