Skip to main content
Advertisement

Main menu

  • Home
  • Articles
    • Current Issue
    • Fast Forward
    • Latest Articles
    • Archive
  • Information
    • Instructions to Authors
    • Submit a Manuscript
    • For Subscribers
    • For Advertisers
    • Terms & Conditions of Use
    • Permissions
  • Editorial Board
  • Alerts
    • Alerts
    • RSS Feeds
  • Virtual Issues
  • Feedback
  • Other Publications
    • Drug Metabolism and Disposition
    • Journal of Pharmacology and Experimental Therapeutics
    • Molecular Pharmacology
    • Pharmacological Reviews
    • Pharmacology Research & Perspectives
    • ASPET

User menu

  • My alerts
  • Log in

Search

  • Advanced search
Drug Metabolism & Disposition
  • Other Publications
    • Drug Metabolism and Disposition
    • Journal of Pharmacology and Experimental Therapeutics
    • Molecular Pharmacology
    • Pharmacological Reviews
    • Pharmacology Research & Perspectives
    • ASPET
  • My alerts
  • Log in
Drug Metabolism & Disposition

Advanced Search

  • Home
  • Articles
    • Current Issue
    • Fast Forward
    • Latest Articles
    • Archive
  • Information
    • Instructions to Authors
    • Submit a Manuscript
    • For Subscribers
    • For Advertisers
    • Terms & Conditions of Use
    • Permissions
  • Editorial Board
  • Alerts
    • Alerts
    • RSS Feeds
  • Virtual Issues
  • Feedback
  • Visit dmd on Facebook
  • Follow dmd on Twitter
  • Follow ASPET on LinkedIn
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
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Magí Farré
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Mitona Pujadas
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Ana Ma͢ Peiró
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Pere N Roset
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Jesús Joglar
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
Rafael de la Torre
  • Find this author on Google Scholar
  • Find this author on PubMed
  • Search for this author on this site
  • Article
  • Figures & Data
  • Info & Metrics
  • eLetters
  • PDF
Loading

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
View Full Text

Log in using your username and password

Forgot your user name or password?

Pay Per Article - You may access this article (from the computer you are currently using) for 1 day for US$35.00

Regain Access - You can regain access to a recent Pay per Article purchase if your access period has not yet expired.

PreviousNext
Back to top

In this issue

Drug Metabolism and Disposition: 32 (9)
Drug Metabolism and Disposition
Vol. 32, Issue 9
1 Sep 2004
  • Table of Contents
  • About the Cover
  • Index by author
Download PDF
Article Alerts
Sign In to Email Alerts with your Email Address
Email Article

Thank you for sharing this Drug Metabolism & Disposition article.

NOTE: We request your email address only to inform the recipient that it was you who recommended this article, and that it is not junk mail. We do not retain these email addresses.

Enter multiple addresses on separate lines or separate them with commas.
STEREOCHEMICAL ANALYSIS OF 3,4-METHYLENEDIOXYMETHAMPHETAMINE AND ITS MAIN METABOLITES IN HUMAN SAMPLES INCLUDING THE CATECHOL-TYPE METABOLITE (3,4-DIHYDROXYMETHAMPHETAMINE)
(Your Name) has forwarded a page to you from Drug Metabolism & Disposition
(Your Name) thought you would be interested in this article in Drug Metabolism & Disposition.
Citation Tools
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;

Citation Manager Formats

  • BibTeX
  • Bookends
  • EasyBib
  • EndNote (tagged)
  • EndNote 8 (xml)
  • Medlars
  • Mendeley
  • Papers
  • RefWorks Tagged
  • Ref Manager
  • RIS
  • Zotero
Share
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;
del.icio.us logo Digg logo Reddit logo Twitter logo CiteULike logo Facebook logo Google logo Mendeley logo
  • Tweet Widget
  • Facebook Like
  • Google Plus One

Jump to section

  • Article
    • Abstract
    • Materials and Methods
    • Results
    • Discussion
    • Acknowledgments
    • Footnotes
    • References
  • Figures & Data
  • Info & Metrics
  • eLetters
  • PDF

Related Articles

Cited By...

More in this TOC Section

  • Abundant expression of OCT2, MATE1, OAT1, OAT3, PEPT2, BCRP, MDR1 and xCT transporters in blood-arachnoid barrier of pig, and polarized localizations at CSF- and blood-facing plasma membranes
  • Pharmacokinetics of Organic Cation Transporter 1 (OCT1) Substrates in Oct1/2 Knockout Mice and Species Difference in Hepatic OCT1-mediated Uptake
  • Human Cytochrome P450 1A1 Adapts Active Site for Atypical Nonplanar Substrate
Show more Articles

Similar Articles

  • Home
  • Alerts
Facebook   Twitter   LinkedIn   RSS

Navigate

  • Current Issue
  • Fast Forward by date
  • Fast Forward by section
  • Latest Articles
  • Archive
  • Search for Articles
  • Feedback
  • ASPET

More Information

  • About DMD
  • Editorial Board
  • Instructions to Authors
  • Submit a Manuscript
  • Customized Alerts
  • RSS Feeds
  • Subscriptions
  • Permissions
  • Terms & Conditions of Use

ASPET's Other Journals

  • Journal of Pharmacology and Experimental Therapeutics
  • Molecular Pharmacology
  • Pharmacological Reviews
  • Pharmacology Research & Perspectives
ISSN 1521-009X (Online)

Copyright © 2019 by the American Society for Pharmacology and Experimental Therapeutics