The metabolism of amphetamine in vitro by rabbit liver preparations: a comparison of R(-) and S(+) enantiomers.

1. Incubation of R(-), S(+) and RS(+/-) amphetamines with rabbit liver 9000 g supernatant indicated that R(-) was metabolized at a faster rate than S(+), but that racemic amphetamine was metabolized at the same rate as S(+) during one hour incubations. 2. N-Hydroxyamphetamine and 1-phenyl-2-propranol were the major compounds detected in both R(-) and S(+) amphetamine incubations. 3. Phenylacetone oxime was detected in significant quantities after 3 h incubations of R(-) amphetamine, but only in minor quantities from S(+). 4. A fall in the amount of N-hydroxyamphetamine present in R(-) amphetamine incubations after a 3 h period as compared to a 1 h incubation, paralleled by a rise in the amount of phenylacetone oxime during 3 h suggested that the oxime was derived as a secondary metabolics from N-hydroxyamphetamine. 5. R(-) and S(+) N-hydroxyamphetamines were both metabolized to phenylacetone oxime by rabbit liver 9000 g supernatant, but the R(-) enantiomer was converted at a faster rate than S(+).