Clinical Chemistry
HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
QUICK SEARCH:   [advanced]


     

Clinical Chemistry 45: 1058-1069, 1999;
This Article
Right arrow Full Text
Right arrow Full Text (PDF)
Right arrow A correction has been published
Right arrow Alert me when this article is cited
Right arrow Alert me if a correction is posted
Right arrow Citation Map
Services
Right arrow Email this article to a friend
Right arrow Similar articles in this journal
Right arrow Similar articles in Web of Science
Right arrow Similar articles in PubMed
Right arrow Alert me to new issues of the journal
Right arrow Download to citation manager
Right arrow reprints & permissions
Citing Articles
Right arrow Citing Articles via HighWire
Right arrow Citing Articles via Web of Science (49)
Right arrow Citing Articles via Google Scholar
Google Scholar
Right arrow Articles by Fallon, J. K.
Right arrow Articles by Hutt, A. J.
Right arrow Search for Related Content
PubMed
Right arrow PubMed Citation
Right arrow Articles by Fallon, J. K.
Right arrow Articles by Hutt, A. J.
Related Collections
Right arrow Drug Monitoring and Toxicology
(Clinical Chemistry. 1999;45:1058-1069.)
© 1999 American Association for Clinical Chemistry, Inc.

Articles

Stereospecific Analysis and Enantiomeric Disposition of 3,4-Methylenedioxymethamphetamine (Ecstasy) in Humans

John K. Fallon1, Andrew T. Kicman1,a, John A. Henry2, Peter J. Milligan3, David A. Cowan1 and Andrew J. Hutt1

1 Drug Control Centre and Department of Pharmacy, King's College London, Manresa Road, London SW3 6LX, UK.

2 Academic Department of Accident and Emergency Medicine, Imperial College School of Medicine, St. Mary's Hospital, London W2 1NY, UK.

3 Computing Centre, King's College London, Campden Hill Road, London W8 7AH, UK.
a Author for correspondence. E-mail andrew.kicman{at}kcl.ac.uk

Background: Little is known concerning the enantioselective disposition of 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) in humans. In addition, the potential of utilizing the stereochemical composition of an analyte in biological media for forensic purposes requires investigation.

Methods: The enantiomers of MDMA and its demethylated metabolite, 3,4-methylenedioxyamphetamine (MDA), present in plasma and urine extracts were derivatized with (-)-(R)-{alpha}-methoxy-{alpha}-trifluoromethylphenylacetyl chloride and analyzed by gas chromatography–mass spectrometry and gas chromatography, respectively. The enantioselective disposition of MDMA and MDA was determined following oral administration of racemic MDMA (40 mg) to eight male volunteers.

Results: The plasma concentrations of (R)-MDMA exceeded those of the S-enantiomer [ratio R:S of the area under the curve (AUC), 2.4 ± 0.3], and the plasma half-life of (R)-MDMA (5.8 ± 2.2 h) was significantly longer than that of the S-enantiomer (3.6 ± 0.9 h). The majority of the recovered material in urine was excreted within 24 h after dosing, with the recovery of (R)-MDMA (21.4% ± 11.6%) being significantly greater than that of (S)-MDMA (9.3% ± 4.9%), and with (S)- and (R)-MDA accounting for 1.4% ± 0.5% and 1.0% ± 0.3% of the dose, respectively. Mathematical modeling of plasma enantiomeric composition vs sampling time demonstrated the applicability of using stereochemical data for the prediction of time elapsed after drug administration.

Conclusions: Analytical methods for determining the enantiomeric composition of MDMA and MDA in plasma and urine were developed. The disposition of MDMA in humans is stereoselective, with the more active S-enantiomer having a reduced AUC and shorter half-life than (R)-MDMA. The determination of stereochemical composition may be applicable for forensic purposes.© 1999 American Association for Clinical Chemistry




The following articles in journals at HighWire Press have cited this article:


Home page
 Drug Metab. Dispos.Home page
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]

Home page
 Drug Metab. Dispos.Home page
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-Methylenedioxyethylamphetamine and Its Single Enantiomers
Drug Metab. Dispos., June 1, 2009; 37(6): 1152 - 1156.
[Abstract] [Full Text] [PDF]

Home page
 Drug Metab. Dispos.Home page
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]

Home page
 Clin. Chem.Home page
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]

Home page
 Clin. Chem.Home page
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]

Home page
 Clin. Chem.Home page
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]

Home page
 Drug Metab. Dispos.Home page
N. Pizarro, M. Farre, M. Pujadas, A. M. Peiro, P. N Roset, J. Joglar, and R. de la Torre
STEREOCHEMICAL ANALYSIS OF 3,4-METHYLENEDIOXYMETHAMPHETAMINE AND ITS MAIN METABOLITES IN HUMAN SAMPLES INCLUDING THE CATECHOL-TYPE METABOLITE (3,4-DIHYDROXYMETHAMPHETAMINE)
Drug Metab. Dispos., September 1, 2004; 32(9): 1001 - 1007.
[Abstract] [Full Text] [PDF]

Home page
 Pharmacol. Rev.Home page
A. R. Green, A. O. Mechan, J. M. Elliott, E. O'Shea, and M. I. Colado
The Pharmacology and Clinical Pharmacology of 3,4-Methylenedioxymethamphetamine (MDMA, "Ecstasy")
Pharmacol. Rev., September 1, 2003; 55(3): 463 - 508.
[Abstract] [Full Text] [PDF]


HOME HELP FEEDBACK SUBSCRIPTIONS ARCHIVE SEARCH TABLE OF CONTENTS
Copyright © 1999 by the American Association for Clinical Chemistry.