![[Feedback]](/icons/banner/feedbackACT.gif){kind=icon}
![[For Subscribers]](/icons/banner/subscriberACT.gif){kind=icon}
![[Archive]](/icons/banner/archiveACT.gif){kind=icon}
![[Search]](/icons/banner/searchACT.gif){kind=icon}
![[Contents]](/icons/banner/tocACT.gif){kind=icon}
|
|
|
|
|
||
Pharmacology Research Unit, Institut Municipal d'Investigació Mèdica (IMIM), Universitat Autònoma de Barcelona and Universitat Pompeu Fabra (N.P., M.F., M.P., A.Ma.P., P.N.R., R.d.l.T.); and Department of Biological Organic Chemistry, Institut d'Investigacions Quimiques i Ambientals, Consell Superior d'Investigacions Científiques (IIQAB-CSIC) (J.J.), Barcelona, Spain
3,4-Methylenedioxymethamphetamine (MDMA; "ecstasy") is a designer drug commonly misused in large segments of young populations. MDMA is usually formulated in tablets of its racemate (1:1 mixture of its enantiomers) in doses ranging from 50 to 200 mg. MDMA has an enantioselective metabolism, the (S)-enantiomer being metabolized faster than the (R)-enantiomer. Different pharmacologic properties have been attributed to each enantiomer. The carbon responsible for MDMA chirality is preserved along its metabolic disposition. An analytical method has been developed to determine MDMA enantiomers and those from its major metabolites, 3,4-methylenedioxyamphetamine (MDA), 3,4-dihydroxymeth-amphetamine (HHMA), and 4-hydroxy-3-methoxymethamphet-amine (HMMA). It has been applied to the analysis of plasma and urine samples from healthy recreational users of MDMA who participated voluntarily in a clinical trial and received 100 mg (R,S)-MDMA · HCl orally. (R)/(S) ratios both in plasma (0-48 h) and urine (0-72 h) for MDMA and MDA were >1 and <1, respectively. Ratios corresponding to HHMA and HMMA, close to unity, deviate from theoretical expectations and are most likely explained by the ability of MDMA to autoinhibit its own metabolism. The short elimination half-life of (S)-MDMA (4.8 h) is consistent with the subjective effects and psychomotor performance reported in subjects exposed to MDMA, whereas the much longer half-life of the (R)-enantiomer (14.8 h) correlates with mood and cognitive effects experienced on the next days after MDMA use.
This article has been cited by other articles:
|
|
 |
|
  A. E. Schwaninger, M. R. Meyer, J. Zapp, and H. H. Maurer The Role of Human UDP-Glucuronyltransferases on the Formation of the Methylenedioxymethamphetamine (Ecstasy) Phase II Metabolites R- and S-3-Methoxymethamphetamine 4-O-Glucuronides Drug Metab. Dispos., November 1, 2009; 37(11): 2212 - 2220. [Abstract] [Full Text] [PDF]
|
|
|
|
|
|
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]
|
|
|
|
 |
|
 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]
|
|
|
|
 |
|
 N. Easton and C. A. Marsden Ecstasy: Are animal data consistent between species and can they translate to humans? J Psychopharmacol, March 1, 2006; 20(2): 194 - 210. [Abstract] [PDF]
|
|
|
|
|
|
F. T. Peters, N. Samyn, C. T.J. Lamers, W. J. Riedel, T. Kraemer, G. de Boeck, and H. H. Maurer Drug Testing in Blood: Validated Negative-Ion Chemical Ionization Gas Chromatographic-Mass Spectrometric Assay for Enantioselective Measurement of the Designer Drugs MDEA, MDMA, and MDA and Its Application to Samples from a Controlled Study with MDMA Clin. Chem., October 1, 2005; 51(10): 1811 - 1822. [Abstract] [Full Text] [PDF]
|
|
 |
 |
 |
|
 |
 |
 |
