Enantioselective determination of 3,4‐methylene‐dioxymethamphetamine and two of its metabolites in human urine by cyclodextrin‐modified capillary zone electrophoresis
- 1 January 1997
- journal article
- application
- Published by Wiley in Electrophoresis
- Vol. 18 (6), 1035-1043
- https://doi.org/10.1002/elps.1150180628
Abstract
Using capillary zone electrophoresis with a phosphate buffer at pH 2.5 containing 30 mM (2-hydroxypropyl)-β-cyclodextrin as chiral selector, the simultaneous separation of the enantiomers of 3,4-methylenedioxymethamphetamine (MDMA or Ecstasy) and its two metabolites 4-hydroxy-3-methoxymethamphetamine (HMMA) and 3,4-methylenedioxyamphetamine (MDA) in human urine is reported. The assay described is based upon enzymatic hydrolysis of conjugated HMMA (major urinary metabolite) and solid-phase extraction followed by injection of a few nL of the extract onto a 50 μm internal diameter (ID) fused-silica capillary of 60 cm length. Solutes are detected via on-column absorbance at 195 nm. For 375 ng/mL drug levels, intraday and interday imprecision is < 4%. With 5 mL urine samples, the detection limit is in the 20–50 ng/mL range. Via analysis of the urines of two patients, the metabolism of MDMA is demonstrated to be enantioselective, with significantly higher urinary amounts of R-(−)-MDMA being excreted compared to S-(+)-MDMA. Within 72h after drug administration one patient was determined to excrete 42.28 and 10.16% of the racemic MDMA dose (1.5 mg/kg body weight) as R-(−) and S-(+)-MDMA enantiomers, respectively. Corresponding values for the second subject were found to be 28.63 and 9.34%. The metabolism of the enantiomers of the two metabolites showed interindividual differences. The first and second detected HMMA enantiomers represented 3.79 and 5.42% (first subject) and 8.51 and 4.36% (second), respectively, of the administered MDMA dose. For the MDA enantiomers, corresponding values were 2.44, 1.76, 0.75, and 0.79%, respectively.Keywords
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