PMID- 11836119 OWN - NLM STAT- MEDLINE DCOM- 20020911 LR - 20190901 IS - 0968-0896 (Print) IS - 0968-0896 (Linking) VI - 10 IP - 4 DP - 2002 Apr TI - Synthesis and capillary electrophoretic analysis of enantiomerically enriched reference standards of MDMA and its main metabolites. PG - 1085-92 AB - 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. FAU - Pizarro, Nieves AU - Pizarro N AD - Pharmacology Research Unit, Institut Municipal d'Investigacio Medica, Doctor Aiguader 80, E-08003, Barcelona, Spain. FAU - de la Torre, Rafael AU - de la Torre R FAU - Farre, Magi AU - Farre M FAU - Segura, Jordi AU - Segura J FAU - Llebaria, Amadeu AU - Llebaria A FAU - Joglar, Jesus AU - Joglar J LA - eng PT - Journal Article PT - Research Support, Non-U.S. Gov't PL - England TA - Bioorg Med Chem JT - Bioorganic & medicinal chemistry JID - 9413298 RN - 0 (Hallucinogens) RN - 0 (Lactates) RN - 15398-87-5 (alpha-methylepinine) RN - 515-30-0 (atrolactic acid) RN - KE1SEN21RM (N-Methyl-3,4-methylenedioxyamphetamine) RN - R7339QLN1C (Deoxyepinephrine) SB - IM MH - Deoxyepinephrine/*analogs & derivatives/analysis/metabolism/standards MH - Electrophoresis, Capillary MH - Hallucinogens/*analysis/metabolism/standards MH - Lactates/analysis/metabolism/standards MH - N-Methyl-3,4-methylenedioxyamphetamine/*analysis/metabolism/standards MH - Reference Standards MH - Stereoisomerism EDAT- 2002/02/12 10:00 MHDA- 2002/09/12 10:01 CRDT- 2002/02/12 10:00 PHST- 2002/02/12 10:00 [pubmed] PHST- 2002/09/12 10:01 [medline] PHST- 2002/02/12 10:00 [entrez] AID - S0968089601003674 [pii] AID - 10.1016/s0968-0896(01)00367-4 [doi] PST - ppublish SO - Bioorg Med Chem. 2002 Apr;10(4):1085-92. doi: 10.1016/s0968-0896(01)00367-4.