title: Synthesis and capillary electrophoretic analysis of enantiomerically enriched reference standards of MDMA and its main metabolites.
abstract: Enantiomerically-enriched (S)-3,4-methylenedioxymethamphetamine (MDMA) and its main metabolites (S)-4-hydroxy-3-methoxymethamphetamine (HMMA) and (S)-3,4-dihydroxymethamphetamine (HHMA) were prepared for unequivocal identification of the differential enantioselective metabolism of these compounds as well as for its application in the analysis of biological samples. Capillary electrophoresis with cyclodextrin derivatives and a chemical correlation of (S)-MDMA, (S)-HMMA and (S)-HHMA has been performed to assign the absolute stereochemistry of major isomers in analytical standards enriched with such enantiomers.
authors.affiliation: Pharmacology Research Unit, Institut Municipal d'Investigació Médica, Doctor Aiguader 80, E-08003, Barcelona, Spain.
authors.forename: Nieves
authors.initials: N
authors.lastname: Pizarro
authors.forename: Rafael
authors.initials: R
authors.lastname: de la Torre
authors.forename: Magí
authors.initials: M
authors.lastname: Farré
authors.forename: Jordi
authors.initials: J
authors.lastname: Segura
authors.forename: Amadeu
authors.initials: A
authors.lastname: Llebaria
authors.forename: Jesús
authors.initials: J
authors.lastname: Joglar
mesh_terms: D003846:Deoxyepinephrine / Q000031:analogs & derivatives* / Q000032:analysis / Q000378:metabolism / Q000592:standards; D019075:Electrophoresis, Capillary; D006213:Hallucinogens / Q000032:analysis* / Q000378:metabolism / Q000592:standards; D007773:Lactates / Q000032:analysis / Q000378:metabolism / Q000592:standards; D018817:N-Methyl-3,4-methylenedioxyamphetamine / Q000032:analysis* / Q000378:metabolism / Q000592:standards; D012015:Reference Standards; D013237:Stereoisomerism
chemical_list: D006213:Hallucinogens; D007773:Lactates; C069512:alpha-methylepinine; C005434:atrolactic acid; D018817:N-Methyl-3,4-methylenedioxyamphetamine; D003846:Deoxyepinephrine