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Volumn 32, Issue 9, 2004, Pages 1001-1007

Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIHYDROXYMETHAMPHETAMINE; 3,4 METHYLENEDIOXYMETHAMPHETAMINE; 4 HYDROXY 3 METHOXYMETHAMPHETAMINE; CARBON; CATECHOL DERIVATIVE; DRUG METABOLITE; UNCLASSIFIED DRUG;

EID: 4143098459     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (54)

References (33)
  • 1
    • 0035835380 scopus 로고    scopus 로고
    • Stereospecific analysis of ecstasy-like N-ethyl-3,4- methylenedioxyamphetamine and its metabolites in humans
    • Brunnenberg M and Kovar K-A (2001) Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans. J Chromatogr B 751:9-18.
    • (2001) J Chromatogr B , vol.751 , pp. 9-18
    • Brunnenberg, M.1    Kovar, K.-A.2
  • 2
    • 0033941158 scopus 로고    scopus 로고
    • Human pharmacology of 3,4-methylenedioxymethamphetamine ("Ecstasy"): Psychomotor performance and subjective effects
    • Camí J, Farré M, Mas M, Roset PN, Poudevida S, Mas A, San L, and de la Torre R (2000) Human pharmacology of 3,4- methylenedioxymethamphetamine ("Ecstasy"): psychomotor performance and subjective effects. J Clin Psychopharmacol 20:455-466.
    • (2000) J Clin Psychopharmacol , vol.20 , pp. 455-466
    • Camí, J.1    Farré, M.2    Mas, M.3    Roset, P.N.4    Poudevida, S.5    Mas, A.6    San, L.7    De La Torre, R.8
  • 3
    • 0030741356 scopus 로고    scopus 로고
    • Mood and cognitive effects of ±3,4-methylenedioxymethamphetamine (MDMA, ecstasy): Week-end "high" followed by mid-week low
    • Curran HV and Travill RA (1997) Mood and cognitive effects of ±3,4-methylenedioxymethamphetamine (MDMA, ecstasy): week-end "high" followed by mid-week low. Addiction 92:821-831.
    • (1997) Addiction , vol.92 , pp. 821-831
    • Curran, H.V.1    Travill, R.A.2
  • 4
    • 0030689047 scopus 로고    scopus 로고
    • Gas chromatographic/mass spectrometric assay for profiling the enantiomers of 3,4-methylenedioxymethamphetamine and its chiral metabolites using positive chemical ionization ion trap mass spectrometry
    • de Boer D, Tan LP, Gorter P, van de Wal RM, Kettenes-van den Bosch JJ, de Bruijn EA, and Maes RA (1997) Gas chromatographic/mass spectrometric assay for profiling the enantiomers of 3,4-methylenedioxymethamphetamine and its chiral metabolites using positive chemical ionization ion trap mass spectrometry. J Mass Spectrom 32:1236-1246.
    • (1997) J Mass Spectrom , vol.32 , pp. 1236-1246
    • De Boer, D.1    Tan, L.P.2    Gorter, P.3    Van De Wal, R.M.4    Kettenes-Van Den Bosch, J.J.5    De Bruijn, E.A.6    Maes, R.A.7
  • 5
    • 0033166574 scopus 로고    scopus 로고
    • Inhibitory metabolite complex formation of methylenedioxymethamphetamine with rat and human cytochrome P450. Particular involvement of CYP2D
    • Delaforge M, Jaouen M, and Bouille G (1999) Inhibitory metabolite complex formation of methylenedioxymethamphetamine with rat and human cytochrome P450. Particular involvement of CYP2D. Environ Toxicol Pharmacol 7:153-158.
    • (1999) Environ Toxicol Pharmacol , vol.7 , pp. 153-158
    • Delaforge, M.1    Jaouen, M.2    Bouille, G.3
  • 9
    • 0029810759 scopus 로고    scopus 로고
    • Metabolism of racemic 3,4-methylenedioxymethamphetamine in humans. Isolation, identification, quantification and synthesis of urinary metabolites
    • Ensslin HK, Maurer HH, Gouzoulis E, Hermle L, and Kovar K-A (1996) Metabolism of racemic 3,4-methylenedioxymethamphetamine in humans. Isolation, identification, quantification and synthesis of urinary metabolites. Drug Metab Dispos 24:813-820.
    • (1996) Drug Metab Dispos , vol.24 , pp. 813-820
    • Ensslin, H.K.1    Maurer, H.H.2    Gouzoulis, E.3    Hermle, L.4    Kovar, K.-A.5
  • 10
    • 0032779463 scopus 로고    scopus 로고
    • Stereospecific analysis and enantiomeric disposition of 3,4-methylenedioxymethamphetamine (ecstasy) in humans
    • Fallon JK, Kicman AT, Henry JA, Milligan PJ, Cowan DA, and Hutt AJ (1999) Stereospecific analysis and enantiomeric disposition of 3,4- methylenedioxymethamphetamine (ecstasy) in humans. Clin Chem 45:1058-1069.
    • (1999) Clin Chem , vol.45 , pp. 1058-1069
    • Fallon, J.K.1    Kicman, A.T.2    Henry, J.A.3    Milligan, P.J.4    Cowan, D.A.5    Hutt, A.J.6
  • 11
    • 0344061038 scopus 로고    scopus 로고
    • Pharmacological characterization of the effects of 3,4- methylenedioxymethamphetamine ("ecstasy") and its enantiomers on lethality, core temperature and locomotor activity in singly housed and crowded mice
    • Fantegrossi WE, Godlewski T, Karabenick RL, Stephens JM, Ullrich T, Rice KC, and Woods JH (2003) Pharmacological characterization of the effects of 3,4-methylenedioxymethamphetamine ("ecstasy") and its enantiomers on lethality, core temperature and locomotor activity in singly housed and crowded mice. Psycopharmacology 166:202-211.
    • (2003) Psycopharmacology , vol.166 , pp. 202-211
    • Fantegrossi, W.E.1    Godlewski, T.2    Karabenick, R.L.3    Stephens, J.M.4    Ullrich, T.5    Rice, K.C.6    Woods, J.H.7
  • 12
    • 0035987117 scopus 로고    scopus 로고
    • 3,4-Methylenedioxymethamphetamine (MDMA, "ecstasy") and its stereoisomers as reinforcers in rhesus monkeys: Serotoninergic involvement
    • Fantegrossi WE, Ullrich T, Rice KC, Woods JH, and Winger G (2002) 3,4-Methylenedioxymethamphetamine (MDMA, "ecstasy") and its stereoisomers as reinforcers in rhesus monkeys: serotoninergic involvement. Psycopharmacology 161:356-364.
    • (2002) Psycopharmacology , vol.161 , pp. 356-364
    • Fantegrossi, W.E.1    Ullrich, T.2    Rice, K.C.3    Woods, J.H.4    Winger, G.5
  • 13
    • 0025685321 scopus 로고
    • Stereoselective pharmacokinetics of 3,4-methylenedioxymethamphetamine in the rat
    • Fitzgerald RL, Blanke RV, and Poklis A (1990) Stereoselective pharmacokinetics of 3,4-methylenedioxymethamphetamine in the rat. Chirality 4:241-248.
    • (1990) Chirality , vol.4 , pp. 241-248
    • Fitzgerald, R.L.1    Blanke, R.V.2    Poklis, A.3
  • 14
    • 0041466261 scopus 로고    scopus 로고
    • The pharmacology and clinical pharmacology of 3,4- methylenedioxymethamphetamine (MDMA, "Ecstasy")
    • Green AR, Mechan AO, JM Elliott, O'Shea E, and Colado MI (2003) The pharmacology and clinical pharmacology of 3,4-methylenedioxymethamphetamine (MDMA, "Ecstasy"). Pharmacol Rev 55:463-508.
    • (2003) Pharmacol Rev , vol.55 , pp. 463-508
    • Green, A.R.1    Mechan, A.O.2    Elliott, J.M.3    O'Shea, E.4    Colado, M.I.5
  • 15
    • 0032827127 scopus 로고    scopus 로고
    • Simultaneous determination of amphetamine, methamphetamine, methylenedioxyamphetamine (MDA), methylenedioxymethamphetamine (MDMA) and methylenedioxyethylamphetamine (MDEA) enantiomers by GC-MS
    • Hensley D and Cody JT (1999) Simultaneous determination of amphetamine, methamphetamine, methylenedioxyamphetamine (MDA), methylenedioxymethamphetamine (MDMA) and methylenedioxyethylamphetamine (MDEA) enantiomers by GC-MS. J Anal Toxicol 23:518-523.
    • (1999) J Anal Toxicol , vol.23 , pp. 518-523
    • Hensley, D.1    Cody, J.T.2
  • 16
    • 0022911226 scopus 로고
    • Effects of the enantiomers of MDA, MDMA and related analogues on [3H]serotonin and [3H]dopamine release from superfused rat brain slices
    • Johnson MP, Hoffman AJ, and Nichols DE (1986) Effects of the enantiomers of MDA. MDMA and related analogues on [3H]serotonin and [3H]dopamine release from superfused rat brain slices. Eur J Pharmacol 132:269-276.
    • (1986) Eur J Pharmacol , vol.132 , pp. 269-276
    • Johnson, M.P.1    Hoffman, A.J.2    Nichols, D.E.3
  • 17
    • 0034092057 scopus 로고    scopus 로고
    • Identification of the human cytochrome P450 involved in the oxidative metabolism of "Ecstasy" related designer drugs
    • Kreth K, Kovar K, Schwab M, and Zanger UM (2000) Identification of the human cytochrome P450 involved in the oxidative metabolism of "Ecstasy" related designer drugs. Biochem Pharmacol 59:1563-1571.
    • (2000) Biochem Pharmacol , vol.59 , pp. 1563-1571
    • Kreth, K.1    Kovar, K.2    Schwab, M.3    Zanger, U.M.4
  • 18
    • 0030915543 scopus 로고    scopus 로고
    • Enantioselective determination of 3,4-methylenedioxymethamphetamine and two of its metabolites in human urine by cyclodextrin-modified capillary zone electrophoresis
    • Lanz M, Brenneisen R, and Thormann W (1997) Enantioselective determination of 3,4-methylenedioxymethamphetamine and two of its metabolites in human urine by cyclodextrin-modified capillary zone electrophoresis. Electrophoresis 18:1035-1043.
    • (1997) Electrophoresis , vol.18 , pp. 1035-1043
    • Lanz, M.1    Brenneisen, R.2    Thormann, W.3
  • 19
    • 0032968382 scopus 로고    scopus 로고
    • Cardiovascular and neuroendocrine effects and pharmacokinetics of 3,4-methylenedioxymethamphetamine in humans
    • Mas M, Farré M, de la Torre R. Roset PN, Ortuño J, Segura J, and Camí J (1999) Cardiovascular and neuroendocrine effects and pharmacokinetics of 3,4-methylenedioxymethamphetamine in humans. J Pharmacol Exp Ther 290:136-145.
    • (1999) J Pharmacol Exp Ther , vol.290 , pp. 136-145
    • Mas, M.1    Farré, M.2    De La Torre, R.3    Roset, P.N.4    Ortuño, J.5    Segura, J.6    Camí, J.7
  • 20
    • 0034653801 scopus 로고    scopus 로고
    • Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ("ecstasy")
    • Maurer HH, Bickeboeller-Friedrich J, Kraemer T, and Peters FT (2000) Toxicokinetics and analytical toxicology of amphetamine-derived designer drugs ("ecstasy"). Toxicol Lett 112-113:133-142.
    • (2000) Toxicol Lett , vol.112-113 , pp. 133-142
    • Maurer, H.H.1    Bickeboeller-Friedrich, J.2    Kraemer, T.3    Peters, F.T.4
  • 21
    • 0037144199 scopus 로고    scopus 로고
    • Enantioselective metabolism of the designer drugs 3,4- methylenedioxymethamphetamine ("ecstasy") and 3,4- methylenedioxyethylamphetamine ("eve") isomers in rat brain and blood
    • Meyer A, Mayerhofer A, Kovar K-A, and Schmidt WJ (2002a) Enantioselective metabolism of the designer drugs 3,4-methylenedioxymethamphetamine ("ecstasy") and 3,4-methylenedioxyethylamphetamine ("eve") isomers in rat brain and blood. Neurosci Lett 330:193-197.
    • (2002) Neurosci Lett , vol.330 , pp. 193-197
    • Meyer, A.1    Mayerhofer, A.2    Kovar, K.-A.3    Schmidt, W.J.4
  • 22
    • 0037183726 scopus 로고    scopus 로고
    • Rewarding effects of the optical isomers of 3,4- methylenedioxymethamphetamine ("ecstasy") and 3,4- methylenedioxyethylamphetamine ("eve") measured by conditioned place preference in rats
    • Meyer A, Mayerhofer A, Kovar K-A. and Schmidt WJ (2002b) Rewarding effects of the optical isomers of 3,4-methylenedioxymethamphetamine ("ecstasy") and 3,4-methylenedioxyethylamphetamine ("eve") measured by conditioned place preference in rats. Neurosci Lett 330:280-284.
    • (2002) Neurosci Lett , vol.330 , pp. 280-284
    • Meyer, A.1    Mayerhofer, A.2    Kovar, K.-A.3    Schmidt, W.J.4
  • 23
    • 4143053372 scopus 로고    scopus 로고
    • The role of metabolism in 3,4(±)-methyledioxyamphetamine and 3,4(±)-methyledioxymethamphetamine (ecstasy) toxicity
    • Monks TJ, Jones DC, Bai F, and Lau SS (2004) The role of metabolism in 3,4(±)-methyledioxyamphetamine and 3,4(±)- methyledioxymethamphetamine (ecstasy) toxicity. Ther Drug Monit 26:132-136.
    • (2004) Ther Drug Monit , vol.26 , pp. 132-136
    • Monks, T.J.1    Jones, D.C.2    Bai, F.3    Lau, S.S.4
  • 24
    • 0030566643 scopus 로고    scopus 로고
    • Distribution of 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) stereoisomers in a fatal poisoning
    • Moore KA, Mozayani A, Fierro MF, and Poklis A (1996) Distribution of 3,4-methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) stereoisomers in a fatal poisoning. Forensic Sci Int 83:111-119.
    • (1996) Forensic Sci Int , vol.83 , pp. 111-119
    • Moore, K.A.1    Mozayani, A.2    Fierro, M.F.3    Poklis, A.4
  • 25
    • 0022838197 scopus 로고
    • Differences between the mechanism of action of MDMA, MBDB and the classic hallucinogens, Identification of a new therapeutic class: Entactogens
    • Nichols DE (1986) Differences between the mechanism of action of MDMA, MBDB and the classic hallucinogens, Identification of a new therapeutic class: entactogens. J Psychoactive Drugs 18:305-313.
    • (1986) J Psychoactive Drugs , vol.18 , pp. 305-313
    • Nichols, D.E.1
  • 26
    • 0036171474 scopus 로고    scopus 로고
    • Synthesis and capillary electrophoretic analysis of enantiomerically enriched reference standards of MDMA and its main metabolites
    • Pizarro N, de la Torre R, Farré M, Segura J, Llebaria A and Joglar I (2002a) Synthesis and capillary electrophoretic analysis of enantiomerically enriched reference standards of MDMA and its main metabolites, Bioorg Med Chem 10:1085-1092.
    • (2002) Bioorg Med Chem , vol.10 , pp. 1085-1092
    • Pizarro, N.1    De La Torre, R.2    Farré, M.3    Segura, J.4    Llebaria, A.5    Joglar, I.6
  • 28
    • 18344382718 scopus 로고    scopus 로고
    • Determination of MDMA and its metabolites in blood and urine by gas chromatography-mass spectrometry and analysis of enantiomers by capillary electrophoresis
    • Pizarro N, Ortuño J, Farré M, Hernández-López C, Pujadas M, Llebaria A, Joglar J, Roset PN, Mas M, Segura J, et al. (2002b) Determination of MDMA and its metabolites in blood and urine by gas chromatography-mass spectrometry and analysis of enantiomers by capillary electrophoresis. J Anal Toxicol 26:157-165.
    • (2002) J Anal Toxicol , vol.26 , pp. 157-165
    • Pizarro, N.1    Ortuño, J.2    Farré, M.3    Hernández-López, C.4    Pujadas, M.5    Llebaria, A.6    Joglar, J.7    Roset, P.N.8    Mas, M.9    Segura, J.10
  • 29
    • 0022338958 scopus 로고
    • Polymorphic dextromethorphan metabolism: Co-segregation of oxidative O-demethylation with debrisoquin hydroxylation
    • Schmid B, Bircher J, Preisig R, and Kupfer A (1985) Polymorphic dextromethorphan metabolism: co-segregation of oxidative O-demethylation with debrisoquin hydroxylation. Clin Pharmacol Ther 38:618-624.
    • (1985) Clin Pharmacol Ther , vol.38 , pp. 618-624
    • Schmid, B.1    Bircher, J.2    Preisig, R.3    Kupfer, A.4
  • 31
    • 18344381770 scopus 로고    scopus 로고
    • High-performance liquid chromatography with electrochemical detection applied to the analysis of 3,4-dihydroxymethamphetamine in human plasma and urine
    • Segura M, Ortuno J, McLure JA, Pujadas M, Pizarro N, Farre M, Llebaria A, Joglar J, Segura J, and de la Torre R (2002) High-performance liquid chromatography with electrochemical detection applied to the analysis of 3,4-dihydroxymethamphetamine in human plasma and urine. J Chromatogr B 769:313-321.
    • (2002) J Chromatogr B , vol.769 , pp. 313-321
    • Segura, M.1    Ortuno, J.2    McLure, J.A.3    Pujadas, M.4    Pizarro, N.5    Farre, M.6    Llebaria, A.7    Joglar, J.8    Segura, J.9    De La Torre, R.10
  • 33
    • 0030218082 scopus 로고    scopus 로고
    • The effects of methylenedioxymeth-amphetamine (MDMA, "Ecstasy") on monoaminergic neurotransmission in the central nervous system
    • White SR, Obradovic T, Imel KM, and Wheaton MJ (1996) The effects of methylenedioxymeth-amphetamine (MDMA, "Ecstasy") on monoaminergic neurotransmission in the central nervous system. Prog Neurobiol 49:455-479.
    • (1996) Prog Neurobiol , vol.49 , pp. 455-479
    • White, S.R.1    Obradovic, T.2    Imel, K.M.3    Wheaton, M.J.4


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