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Research ArticleArticle

STEREOCHEMICAL ANALYSIS OF 3,4-METHYLENEDIOXYMETHAMPHETAMINE AND ITS MAIN METABOLITES IN HUMAN SAMPLES INCLUDING THE CATECHOL-TYPE METABOLITE (3,4-DIHYDROXYMETHAMPHETAMINE)

Nieves Pizarro, Magí Farré, Mitona Pujadas, Ana Ma͢ Peiró, Pere N Roset, Jesús Joglar and Rafael de la Torre
Drug Metabolism and Disposition September 2004, 32 (9) 1001-1007;
Nieves Pizarro
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Magí Farré
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Mitona Pujadas
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Ana Ma͢ Peiró
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Pere N Roset
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Jesús Joglar
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Rafael de la Torre
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Abstract

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.

Footnotes

  • This work was supported by Fonds de Investigaciones Sanitarias (98/0181, 00/0777, 01/1325 and 01/1336) and Generalitat de Catalunya-Department de Recerca i Societat de la Informació (1999/SGR/0242 and 2001/SGR/00407).

  • ABBREVIATIONS: MDMA, 3,4-methylenedioxymethamphetamine; MDA, 3,4-methylenedioxyamphetamine; MDEA, 3,4-methylenedioxyethylam-phetamine; HHMA, 3,4-dihydroxymethamphetamine; HMMA, 4-hydroxy-3-methoxymethamphetamine; HMA, 4-hydroxy-3-methoxyamphet-amine; MDMA-D5, 1-[3,4-(methylenedioxy)phenyl]-2-(1,2-dideutero-3,3,3-trideuteromethylaminopropane); MDA-D5, 1-[3,4-(methylenedioxy)phenyl)]-2-(1,2,3,3,3-pentadeuteroaminopropane; MTP, (R)-(-)-α-methoxy-α-trifluoromethylphenylacetyl derivative; TMS, trimethylsilyl derivative; DHBA, 3,4-dihydroxybenzylamine; GC/MS, gas chromatography/mass spectrometry; CE, capillary electrophoresis; SCX, strong cation exchange; BEC, bond elut certify; IS, internal standard; COMT, catechol-O-methyltransferase; Cmax, maximum concentration; tmax, maximum time; AUC, area under the curve; AUC0-48 h, area under the curve from 0 to 48 h; AUCtotal, area under the curve from 0 to infinity; ke, elimination rate constant; t1/2, elimination half-time.

    • Received March 3, 2004.
    • Accepted May 24, 2004.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 32 (9)
Drug Metabolism and Disposition
Vol. 32, Issue 9
1 Sep 2004
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STEREOCHEMICAL ANALYSIS OF 3,4-METHYLENEDIOXYMETHAMPHETAMINE AND ITS MAIN METABOLITES IN HUMAN SAMPLES INCLUDING THE CATECHOL-TYPE METABOLITE (3,4-DIHYDROXYMETHAMPHETAMINE)
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Research ArticleArticle

STEREOCHEMICAL ANALYSIS OF 3,4-METHYLENEDIOXYMETHAMPHETAMINE AND ITS MAIN METABOLITES IN HUMAN SAMPLES INCLUDING THE CATECHOL-TYPE METABOLITE (3,4-DIHYDROXYMETHAMPHETAMINE)

Nieves Pizarro, Magí Farré, Mitona Pujadas, Ana Ma͢ Peiró, Pere N Roset, Jesús Joglar and Rafael de la Torre
Drug Metabolism and Disposition September 1, 2004, 32 (9) 1001-1007;

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Research ArticleArticle

STEREOCHEMICAL ANALYSIS OF 3,4-METHYLENEDIOXYMETHAMPHETAMINE AND ITS MAIN METABOLITES IN HUMAN SAMPLES INCLUDING THE CATECHOL-TYPE METABOLITE (3,4-DIHYDROXYMETHAMPHETAMINE)

Nieves Pizarro, Magí Farré, Mitona Pujadas, Ana Ma͢ Peiró, Pere N Roset, Jesús Joglar and Rafael de la Torre
Drug Metabolism and Disposition September 1, 2004, 32 (9) 1001-1007;
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