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Drug Monitoring and Toxicology |
1 Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, University of Saarland, Homburg, Germany.
2 National Institute of Criminalistics and Criminology, Brussels, Belgium.
3 Experimental Psychopharmacology Unit, Brain & Behaviour Institute, Maastricht University, Maastricht, The Netherlands.
aAddress correspondence to this author at: Department of Experimental and Clinical Toxicology, Institute of Experimental and Clinical Pharmacology and Toxicology, University of Saarland, D-66421 Homburg (Saar), Germany. Fax 49-6841-16-26051; e-mail hans.maurer{at}uniklinikum-saarland.de.
Background: The enantiomers of the designer drugs 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxymethamphetamine (MDMA), and 3,4-methylenedioxyethylamphetamine (MDEA) differ in their pharmacologic and toxicologic potency. The aim of this study was to develop an assay for measuring these enantiomers in small plasma volumes and to analyze samples from a controlled study with MDMA.
Methods: The analytes were extracted from 
0.2 mL of plasma by mixed-mode solid-phase extraction. After derivatization with S-(–)-heptafluorobutyrylprolyl chloride, the resulting diastereomers were separated by gas chromatography (HP-5MS) within 17 min and detected by mass spectrometry in the negative-ion chemical ionization mode. The method was fully validated and applied to samples from a controlled study in which a single dose of racemic MDMA (75 mg) was administered.
Results: The derivatized enantiomers were well separated and detected with good sensitivity. The assay was linear (per enantiomer) at 1–50 µg/L for MDA and 5–250 µg/L for MDMA and MDEA. Analytical recovery, accuracy, repeatability, and intermediate precision data were within required limits. Extraction yields were 82.1%–95.3%. In the study samples, concentrations of R-(–)-MDMA significantly exceeded those of S-(+)-MDMA. Their ratios (R vs S) were always >1.0 and increased over time. Concentrations of S-(+)-MDA exceeded those of R-(–)-MDA, their ratios (R vs S) also increasing over time but remaining <1.0.
Conclusions: This assay enables sensitive, reliable, and fast enantioselective measurement of MDA, MDMA, and MDEA in small volumes of plasma. The controlled study data confirm previous findings of MDMA and MDA enantiomer ratios (R vs S) increasing over time after ingestion of racemic MDMA.
The following articles in journals at HighWire Press have cited this article:
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  M. R. Meyer, F. T. Peters, and H. H. Maurer The Role of Human Hepatic Cytochrome P450 Isozymes in the Metabolism of Racemic 3,4-Methylenedioxy-Methamphetamine and Its Enantiomers Drug Metab. Dispos., November 1, 2008; 36(11): 2345 - 2354. [Abstract] [Full Text] [PDF]
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 E. A. Kolbrich, R. H. Lowe, and M. A. Huestis Two-Dimensional Gas Chromatography/Electron-Impact Mass Spectrometry with Cryofocusing for Simultaneous Quantification of MDMA, MDA, HMMA, HMA, and MDEA in Human Plasma Clin. Chem., February 1, 2008; 54(2): 379 - 387. [Abstract] [Full Text] [PDF]
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F. T. Peters, N. Samyn, T. Kraemer, W. J. Riedel, and H. H. Maurer Negative-Ion Chemical Ionization Gas Chromatography-Mass Spectrometry Assay for Enantioselective Measurement of Amphetamines in Oral Fluid: Application to a Controlled Study with MDMA and Driving Under the Influence Cases Clin. Chem., April 1, 2007; 53(4): 702 - 710. [Abstract] [Full Text] [PDF]
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S. O. Pirnay, T. T. Abraham, and M. A. Huestis Sensitive Gas Chromatography-Mass Spectrometry Method for Simultaneous Measurement of MDEA, MDMA, and Metabolites HMA, MDA, and HMMA in Human Urine Clin. Chem., September 1, 2006; 52(9): 1728 - 1734. [Abstract] [Full Text] [PDF]
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