title: Stereochemical aspects of para-chloroamphetamine metabolism. Rabbit liver microsomal metabolism of RS-, R(-)-. and S(+)-para-chloroamphetamine.
abstract: With the aid of a chiral derivatizing reagent and a sensitive and specific nitrogen-phosphorus gas chromatographic assay, metabolism of para-chloroamphetamine (PCA) enantiomers has been studied following incubation of racemic (RS)-, R(-)- and S(+)-PCA with rabbit liver microsomal preparations. Significant metabolism of racemic PCA and the individual enantiomers was observed following incubation in rabbit liver microsomal preparations. Metabolism required viable microsomes, NADPH and Molecular oxygen, and the rate of metabolism increased following pretreatment with phenobarbital. Incubation of racemic PCA resulted in more rapid metabolism of the S(+) enantiomer than of the R(-) enantiomer. When the enantiomers were incubated individually, each enantiomer was metabolized more rapidly than when incubated as part of a racemic mixture, and the R(-) enantiomer was metabolized more rapidly than the S(+) enantiomer.
mesh_terms: D000662:Amphetamines / Q000378:metabolism*; D000818:Animals; D001711:Biotransformation; D002849:Chromatography, Gas; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D011817:Rabbits; D051381:Rats; D013237:Stereoisomerism; D010133:p-Chloroamphetamine / Q000378:metabolism*
chemical_list: D000662:Amphetamines; D010133:p-Chloroamphetamine