In vitro stereoselective metabolism of the psychotomimetic amine, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane. An apparent enantiomeric interaction

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Abstract
The stereoselective metabolism [R/S (metabolized) < 1] of the psychotomimetic amine (R,S)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane in 10,000 g rabbit liver homogenate supernatant and 100,000 g microsomal fractions was demonstrated with the aid of the chiral reagent (S)-N-pentafluorobenzoylprolyl-1-imidazolide and GLC analyses. In contrast to the enantiomeric discrimination observed with racemic amine, the individual isomers were metabolized at approximatley the same rate. This apparent enantiomeric interaction illustrates the fact that racemates should be viewed as unique chemical species with pharmacodynamic and toxicologic profiles potentially different from the individual antipodes.