Metabolism of cathinone to (-)-norephedrine and (-)-norpseudoephedrine.
S-(-)-Cathinone (S-(-)-alpha-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 R/R-(-)-norpseudoephedrine. Both aminoalcohols are formed by a stereospecific keto reduction.
Brenneisen
R
R
Geisshüsler
S
S
Schorno
X
X
D000470:Alkaloids / Q000378:metabolism* / Q000652:urine; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D008297:Male; D010665:Phenylpropanolamine / Q000652:urine*; D013237:Stereoisomerism
D000470:Alkaloids; C005331:norpseudoephedrine; D010665:Phenylpropanolamine; C023665:cathinone