Lee, Sangkyu Yoo, Hye Hyun In, Moon Kyo Jin, Changbae Kim, Dong Hyun 2024-01-20T11:03:49Z 2024-01-20T11:03:49Z 2021-09-05 2013-11 0253-6269 https://pubs.kist.re.kr/handle/201004/127471 N,N-Dimethylamphetamine (DMA), a methamphetamine (MA) analog, is known as a weak central nervous system stimulant. As DMA possesses a chiral center, we investigated the enantioselective formation of N,N-dimethylamphetamine N-oxide (DMANO) and MA from DMA using human liver microsomes, recombinant cytochrome P450 (CYP) 2D6, and flavin monooxygenases (FMO) 1 and 3. d-DMA was preferentially metabolized to MA, whereas l-DMA was more rapidly transformed to DMANO in human liver microsomes. CYP2D6 showed a preference for catalyzing N-demethylation of d-DMA, and the intrinsic clearance (Clint) ratio of d-isomer to l-isomer was 1.41. FMO1 catalyzed the formation of slightly less d-DMANO than l-DMANO, and the Clint ratio of the d- to l-isomer was 0.78. The reverse was observed for the formation of DMANO by FMO3. However, given the minor contribution of FMO3 compared with FMO1, it would not affect the overall enantioselective formation of DMANO in human liver microsomes. Enantioselectivities in the formation of MA and DMANO in human liver microsomes were consistent with those of CYP2D6 and FMO1, respectively. English PHARMACEUTICAL SOC KOREA IN-VITRO METABOLISM CAPILLARY-ELECTROPHORESIS MASS SPECTROMETRY METHAMPHETAMINE AMPHETAMINE DIMETHYLAMPHETAMINE HYDROXYLATION CYP2D6 URINE RAT Stereoselectivity in the cytochrome P450-dependent N-demethylation and flavin monooxygenase-dependent N-oxidation of N,N-dimethylamphetamine Article 10.1007/s12272-013-0137-z 1 ARCHIVES OF PHARMACAL RESEARCH, v.36, no.11, pp.1385 - 1391 ARCHIVES OF PHARMACAL RESEARCH 36 11 1385 1391 scie scopus kci ART001902844 000326688100012 2-s2.0-84888138404 Chemistry, Medicinal Pharmacology & Pharmacy Pharmacology & Pharmacy Article IN-VITRO METABOLISM CAPILLARY-ELECTROPHORESIS MASS SPECTROMETRY METHAMPHETAMINE AMPHETAMINE DIMETHYLAMPHETAMINE HYDROXYLATION CYP2D6 URINE RAT Dimethylamphetamine Enantiomeric metabolism CYP2D6 FMO1 FMO3