Literature DB >> 19183967

Hydrolysis of 3,4-methylenedioxymethamphetamine (MDMA) metabolite conjugates in human, squirrel monkey, and rat plasma.

Melanie Mueller1, Erin A Kolbrich-Spargo, Frank T Peters, Marilyn A Huestis, George A Ricaurte, Hans H Maurer.   

Abstract

Characterizing the formation of metabolites of 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy") in different species (rat, squirrel monkey, and human) may provide insight into mechanisms of MDMA neurotoxicity. Two prominent MDMA metabolites, 3,4-dihydroxymethamphetamine (HHMA) and 4-hydroxy-3-methoxymethamphetamine (HMMA), are conjugated with glucuronic or sulfuric acid, but reference standards are not available; therefore, quantification is only possible after conjugate cleavage. Different concentrations of HHMA and HMMA were obtained in human, squirrel monkey, and rat plasma specimens when acid or enzymatic cleavage was performed. Our data document that these differences are due to species-specific influences on conjugate cleavage. Acidic hydrolysis should be used for analyzing free HHMA and HMMA in human or squirrel monkey plasma, while enzymatic hydrolysis with glucuronidase or sulfatase maximizes recovery of free HHMA and HMMA in rat plasma. Optimization of cleavage conditions showed that sulfate conjugates were more readily cleaved by acid hydrolysis and glucuronides by glucuronidase.

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Year:  2009        PMID: 19183967      PMCID: PMC3163102          DOI: 10.1007/s00216-009-2607-1

Source DB:  PubMed          Journal:  Anal Bioanal Chem        ISSN: 1618-2642            Impact factor:   4.142


  39 in total

1.  3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose.

Authors:  B Esteban; E O'Shea; J Camarero; V Sanchez; A R Green; M I Colado
Journal:  Psychopharmacology (Berl)       Date:  2001-03       Impact factor: 4.530

2.  Purification and characterization of arylsulfatase from Sphingomonas sp. AS6330.

Authors:  J-H Kim; D-S Byun; J S Godber; J-S Choi; W-C Choi; H-R Kim
Journal:  Appl Microbiol Biotechnol       Date:  2003-11-05       Impact factor: 4.813

3.  3,4-Dihydroxymethamphetamine (HHMA). A major in vivo 3,4-methylenedioxymethamphetamine (MDMA) metabolite in humans.

Authors:  M Segura; J Ortuño; M Farré; J A McLure; M Pujadas; N Pizarro; A Llebaria; J Joglar; P N Roset; J Segura; R de La Torre
Journal:  Chem Res Toxicol       Date:  2001-09       Impact factor: 3.739

4.  Efficient cleavage of conjugates of drugs or poisons by immobilized beta-glucuronidase and arylsulfatase in columns.

Authors:  S W Toennes; H H Maurer
Journal:  Clin Chem       Date:  1999-12       Impact factor: 8.327

Review 5.  The pharmacology and toxicology of "ecstasy" (MDMA) and related drugs.

Authors:  H Kalant
Journal:  CMAJ       Date:  2001-10-02       Impact factor: 8.262

6.  Determination of MDMA and its metabolites in blood and urine by gas chromatography-mass spectrometry and analysis of enantiomers by capillary electrophoresis.

Authors:  Nieves Pizarro; Jordi Ortuño; Magí Farré; Cándido Hernández-López; Mitona Pujadas; Amadeu Llebaria; Jesús Joglar; Pere N Roset; Marta Mas; Jordi Segura; Jordi Camí; Rafael de la Torre
Journal:  J Anal Toxicol       Date:  2002-04       Impact factor: 3.367

Review 7.  Amphetamines: an update on forensic issues.

Authors:  B K Logan
Journal:  J Anal Toxicol       Date:  2001 Jul-Aug       Impact factor: 3.367

8.  Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ('Ecstasy').

Authors:  H H Maurer; J Bickeboeller-Friedrich; T Kraemer; F T Peters
Journal:  Toxicol Lett       Date:  2000-03-15       Impact factor: 4.372

Review 9.  Human pharmacology of MDMA: pharmacokinetics, metabolism, and disposition.

Authors:  Rafael de la Torre; Magí Farré; Pere N Roset; Neus Pizarro; Sergio Abanades; Mireia Segura; Jordi Segura; Jordi Camí
Journal:  Ther Drug Monit       Date:  2004-04       Impact factor: 3.681

10.  Direct determination of glucuronide and sulfate of 4-hydroxy-3-methoxymethamphetamine, the main metabolite of MDMA, in human urine.

Authors:  Noriaki Shima; Hiroe Kamata; Munehiro Katagi; Hitoshi Tsuchihashi; Tsutomu Sakuma; Nobuo Nemoto
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2007-07-10       Impact factor: 3.205

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  5 in total

1.  Urinary excretion kinetics of 3,4-methylenedioxymethamphetamine (MDMA, ecstasy) and its phase I and phase II metabolites in humans following controlled MDMA administration.

Authors:  Andrea E Schwaninger; Markus R Meyer; Allan J Barnes; Erin A Kolbrich-Spargo; David A Gorelick; Robert S Goodwin; Marilyn A Huestis; Hans H Maurer
Journal:  Clin Chem       Date:  2011-10-06       Impact factor: 8.327

2.  Inhibition of 3,4-methylenedioxymethamphetamine metabolism leads to marked decrease in 3,4-dihydroxymethamphetamine formation but no change in serotonin neurotoxicity: implications for mechanisms of neurotoxicity.

Authors:  Melanie Mueller; Jie Yuan; Concepcion Maldonado Adrian; Una D McCann; George A Ricaurte
Journal:  Synapse       Date:  2011-03-28       Impact factor: 2.562

3.  Studies of (±)-3,4-methylenedioxymethamphetamine (MDMA) metabolism and disposition in rats and mice: relationship to neuroprotection and neurotoxicity profile.

Authors:  Melanie Mueller; Concepcion Maldonado-Adrian; Jie Yuan; Una D McCann; George A Ricaurte
Journal:  J Pharmacol Exp Ther       Date:  2012-12-03       Impact factor: 4.030

4.  Stable isotope- and mass spectrometry-based metabolomics as tools in drug metabolism: a study expanding tempol pharmacology.

Authors:  Fei Li; Xiaoyan Pang; Kristopher W Krausz; Changtao Jiang; Chi Chen; John A Cook; Murali C Krishna; James B Mitchell; Frank J Gonzalez; Andrew D Patterson
Journal:  J Proteome Res       Date:  2013-01-31       Impact factor: 4.466

5.  3,4-Methylenedioxypyrovalerone (MDPV) and metabolites quantification in human and rat plasma by liquid chromatography-high resolution mass spectrometry.

Authors:  Sebastien Anizan; Kayla Ellefsen; Marta Concheiro; Masaki Suzuki; Kenner C Rice; Michael H Baumann; Marilyn A Huestis
Journal:  Anal Chim Acta       Date:  2014-04-12       Impact factor: 6.558

  5 in total

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