INVITRO METABOLISM OF AMPHETAMINE - APPARENT ENANTIOMERIC INTERACTION

  • 1 January 1976
    • journal article
    • research article
    • Vol. 15  (3) , 525-540
Abstract
The stereoselective formation of the major metabolites N-hydroxyamphetamine and 1-phenyl-2-propanol was studied in incubations of amphetamine with 9,000 .times. g supernatant fractions of rabbit liver using deuterium, labelling in conjunction with selected-ion-monitoring gas chromatography/mass spectrometry. Comparison of separate incubations of (R)-amphetamine with those of (S)-amphetamine-d3 and of (S)-amphetamine with those of (R)-amphetamine-d3 showed that larger amounts of the 2 metabolites were formed from the (R) enantiomer. When pseudoracemic mixture (R)-amphetamine/(S)-amphetamine-d3 or (R)-amphetamine-d3/(S)-amphetamine were incubated the 2 metabolites were preferentially formed from the (S) enantiomer. Studies on the disappearance of substrate during incubation gave results in agreement with the findings on stereoselective metabolite formation. (S)-Amphetamine or 1 of its metabolites inhibits the metabolism of the (R) enantiomer.

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