Metabolism of cathinone to (−)-norephedrine and (−)-norpseudoephedrine

Abstract

Abstract S-(−)-Cathinone (S-(−)-α-aminopropiophenone) is the major active principle of khat leaves (Catha edulis), which are widely used in East Africa and the Arab peninsula as an amphetamine-like stimulant. After oral administration of synthesized cathinone (isomers, racemate), 22–52% was recovered in 24 h urine samples mainly as aminoalcohol metabolites. With GC/MS, HPLC and CD, the main metabolite of S-(−)-cathinone was identified as R/S-(−)-norephedrine and the main metabolite of R-(+)-cathinone as RR-(−)-norpseudoephedrine. Both aminoalcohols are formed by a stereospecific keto reduction.