메뉴 건너뛰기




Volumn 23, Issue 1, 2010, Pages 211-219

Synthesis and in vitro cytotoxicity profile of the R-enantiomer of 3,4-dihydroxymethamphetamine (R-(-)-HHMA): Comparison with related catecholamines

Author keywords

[No Author keywords available]

Indexed keywords

3,4 DIHYDROXYMETHAMPHETAMINE; 3,4 METHYLENEDIOXYMETHAMPHETAMINE; 5 (N ACETYLCYSTEIN S YL) N METHYL R METHYLDOPAMINE; CATECHOL; CATECHOLAMINE; LEVODOPA; PROPIDIUM IODIDE; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

EID: 75149197655     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx9003374     Document Type: Article
Times cited : (7)

References (50)
  • 1
    • 0030040183 scopus 로고    scopus 로고
    • Pathology of deaths associated with "ecstasy" and "eve" misuse
    • Milroy, C. M., Clark, J. C., and Forrest, A. R. W. (1996) Pathology of deaths associated with "ecstasy" and "eve" misuse. J. Clin. Pathol. 49, 149-153.
    • (1996) J. Clin. Pathol , vol.49 , pp. 149-153
    • Milroy, C.M.1    Clark, J.C.2    Forrest, A.R.W.3
  • 2
    • 0033060517 scopus 로고    scopus 로고
    • Fatal multi-organ failure after suicidal overdose with MDMA, "ecstasy": Case report and review of the literature
    • Walubo, A., and Seger, D. (1999) Fatal multi-organ failure after suicidal overdose with MDMA, "ecstasy": case report and review of the literature. Hum. Exp. Toxicol. 18, 119-125.
    • (1999) Hum. Exp. Toxicol , vol.18 , pp. 119-125
    • Walubo, A.1    Seger, D.2
  • 3
    • 0032881255 scopus 로고    scopus 로고
    • Adam (MDMA) and Eve (MDA) misuse: An immunohistochemical study on three fatal cases
    • Fineschi, V., Centini, F., Mazzeo, E., and Turillazzi, E. (1999) Adam (MDMA) and Eve (MDA) misuse: an immunohistochemical study on three fatal cases. Forensic Sci. Int. 104, 65-74.
    • (1999) Forensic Sci. Int , vol.104 , pp. 65-74
    • Fineschi, V.1    Centini, F.2    Mazzeo, E.3    Turillazzi, E.4
  • 4
    • 0037377537 scopus 로고    scopus 로고
    • Altered states: The clinical effects of ecstasy
    • Cole, J. C., and Sumnall, H. R. (2003) Altered states: the clinical effects of ecstasy. Pharmacol. Ther. 98, 35-58.
    • (2003) Pharmacol. Ther , vol.98 , pp. 35-58
    • Cole, J.C.1    Sumnall, H.R.2
  • 5
    • 20444498341 scopus 로고    scopus 로고
    • Recognition and management of complications of new recreational drug use
    • Ricaurte, G. A., and McCann, U. D. (2005) Recognition and management of complications of new recreational drug use. Lancet 365, 2137-2145.
    • (2005) Lancet , vol.365 , pp. 2137-2145
    • Ricaurte, G.A.1    McCann, U.D.2
  • 6
    • 0041466261 scopus 로고    scopus 로고
    • The pharmacology and clinical pharmacology of 3,4- methylenedioxymethamphetamine (MDMA, "ecstasy")
    • and references therein
    • Green, A. R., Mechan, A. O., Elliot, J. M., O'Shea, E., and Colado, M. I. (2003) The pharmacology and clinical pharmacology of 3,4- methylenedioxymethamphetamine (MDMA, "ecstasy"). Pharmacol. Rev. 55, 463-508, and references therein.
    • (2003) Pharmacol. Rev , vol.55 , pp. 463-508
    • Green, A.R.1    Mechan, A.O.2    Elliot, J.M.3    O'Shea, E.4    Colado, M.I.5
  • 7
    • 0037651952 scopus 로고    scopus 로고
    • Methylenedioxymethamphetamine (MDMA, Ecstasy) neurotoxicity: Cellular and molecular mechanisms
    • and references therein
    • Lyles, J., and Cadet, J. L. (2003) Methylenedioxymethamphetamine (MDMA, Ecstasy) neurotoxicity: cellular and molecular mechanisms. Brain Res. Rev. 42, 155-168, and references therein.
    • (2003) Brain Res. Rev , vol.42 , pp. 155-168
    • Lyles, J.1    Cadet, J.L.2
  • 8
    • 12344323600 scopus 로고    scopus 로고
    • Ecstasy: Pharmacology and neurotoxicity
    • Morton, J. (2005) Ecstasy: pharmacology and neurotoxicity. Curr. Opin. Pharmacol. 5, 79-86.
    • (2005) Curr. Opin. Pharmacol , vol.5 , pp. 79-86
    • Morton, J.1
  • 9
    • 33751230490 scopus 로고    scopus 로고
    • 3,4- methylenedioxymethamphetamine (MDMA) neurotoxicity in rats: A reappraisal of past and present findings
    • Baumann, M. H., Wang, X., and Rothman, R. B. (2007) 3,4- methylenedioxymethamphetamine (MDMA) neurotoxicity in rats: a reappraisal of past and present findings. Psychopharmacology 189, 407-424.
    • (2007) Psychopharmacology , vol.189 , pp. 407-424
    • Baumann, M.H.1    Wang, X.2    Rothman, R.B.3
  • 11
    • 44649173724 scopus 로고    scopus 로고
    • Action of 3,4-methylenedioxymethamphetamine (MDMA) on cerebral dopaminergic, serotonergic and cholinergic neurons
    • Gudelsky, G. A., and Yamamoto, B. K. (2008) Action of 3,4-methylenedioxymethamphetamine (MDMA) on cerebral dopaminergic, serotonergic and cholinergic neurons. Pharmacol., Biochem. Behav. 90, 198-207.
    • (2008) Pharmacol., Biochem. Behav , vol.90 , pp. 198-207
    • Gudelsky, G.A.1    Yamamoto, B.K.2
  • 12
    • 69449095628 scopus 로고    scopus 로고
    • Molecular and cellular mechanisms of ecstasy-induced neurotoxicity: An overview
    • and references therein
    • Capela, J. P., Carmo, H., Remiao, F., Lourdes Bastos, M., Meisel, A., and Carvalho, F. (2009) Molecular and cellular mechanisms of ecstasy-induced neurotoxicity: an overview. Mol. Neurobiol. 39, 210-271, and references therein.
    • (2009) Mol. Neurobiol , vol.39 , pp. 210-271
    • Capela, J.P.1    Carmo, H.2    Remiao, F.3    Lourdes Bastos, M.4    Meisel, A.5    Carvalho, F.6
  • 13
    • 40849129898 scopus 로고    scopus 로고
    • On the role of tyrosine and peripheral metabolism in 3,4-methylenedioxymethamphetamine-induced serotonin neurotoxicity in rats
    • Goni-Allo, B., Puerta, E., Mathuna, B. O., Hervias, I., Lasheras, B., de la Torre, R., and Aguirre, N. (2008) On the role of tyrosine and peripheral metabolism in 3,4-methylenedioxymethamphetamine-induced serotonin neurotoxicity in rats. Neuropharmacology 54, 885-900.
    • (2008) Neuropharmacology , vol.54 , pp. 885-900
    • Goni-Allo, B.1    Puerta, E.2    Mathuna, B.O.3    Hervias, I.4    Lasheras, B.5    de la Torre, R.6    Aguirre, N.7
  • 14
    • 0035084704 scopus 로고    scopus 로고
    • 3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose
    • Esteban, B., O'Shea, E., Camarero, J., Sanchez, V., Green, A. R., and Colado, M. I. (2001) 3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose. Psychopharmacology 154, 251-260.
    • (2001) Psychopharmacology , vol.154 , pp. 251-260
    • Esteban, B.1    O'Shea, E.2    Camarero, J.3    Sanchez, V.4    Green, A.R.5    Colado, M.I.6
  • 15
    • 4143053372 scopus 로고    scopus 로고
    • The role of metabolism in 3, 4-(±)-methylenedioxyamphetamine and 3,4-(±)- methylenedioxymethamphetamine (Ecstasy) toxicity
    • Monks, T. J., Jones, D. C., Bai, F., and Lau, S. S. (2004) The role of metabolism in 3, 4-(±)-methylenedioxyamphetamine and 3,4-(±)- methylenedioxymethamphetamine (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
  • 18
    • 34248589634 scopus 로고    scopus 로고
    • Bacterial plate assays and electrochemical methods: An efficient tandem for evaluating the ability of catecholthioether metabolites of MDMA ("ecstasy") to induce toxic effects through redox-cycling
    • Felim, A., Urios, A., Neudörffer, A., Herrera, G., Blanco, M., and Largeron, M. (2007) Bacterial plate assays and electrochemical methods: an efficient tandem for evaluating the ability of catecholthioether metabolites of MDMA ("ecstasy") to induce toxic effects through redox-cycling. Chem. Res. Toxicol. 20, 685-693.
    • (2007) Chem. Res. Toxicol , vol.20 , pp. 685-693
    • Felim, A.1    Urios, A.2    Neudörffer, A.3    Herrera, G.4    Blanco, M.5    Largeron, M.6
  • 21
    • 37349127647 scopus 로고    scopus 로고
    • Accumulation of neurotoxic thioether metabolites of 3,4-(±)-methylenedioxymethamphetamine in rat brain
    • Erives, G. V., Lau, S. S., and Monks, T. J. (2008) Accumulation of neurotoxic thioether metabolites of 3,4-(±)-methylenedioxymethamphetamine in rat brain. J. Pharmacol. Exp. Ther. 324, 284-291.
    • (2008) J. Pharmacol. Exp. Ther , vol.324 , pp. 284-291
    • Erives, G.V.1    Lau, S.S.2    Monks, T.J.3
  • 22
    • 58149083155 scopus 로고    scopus 로고
    • Serotonergic neurotoxic thioether metabolites of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy"): Synthesis, isolation and characterization of diastereoisomers
    • Pizarro, N., de la Torre, R., Joglar, J., Okumura, N., Perfetti, X., Lau, S. S., and Monks, T. J. (2008) Serotonergic neurotoxic thioether metabolites of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy"): synthesis, isolation and characterization of diastereoisomers. Chem. Res. Toxicol. 21, 2272-2279.
    • (2008) Chem. Res. Toxicol , vol.21 , pp. 2272-2279
    • Pizarro, N.1    de la Torre, R.2    Joglar, J.3    Okumura, N.4    Perfetti, X.5    Lau, S.S.6    Monks, T.J.7
  • 23
    • 54349126394 scopus 로고    scopus 로고
    • The role of human hepatic cytochrome P450 isoenzymes in the metabolism of racemic 3, 4-methylenedioxymethamphetamine and its enantiomers
    • Meyer, M. R., Peters, F. T., and Maurer, H. H. (2008) The role of human hepatic cytochrome P450 isoenzymes in the metabolism of racemic 3, 4-methylenedioxymethamphetamine and its enantiomers. Drug Metab. Dispos. 36, 2345-2354.
    • (2008) Drug Metab. Dispos , vol.36 , pp. 2345-2354
    • Meyer, M.R.1    Peters, F.T.2    Maurer, H.H.3
  • 24
    • 0018116496 scopus 로고
    • Absolute Configuration and Psychotomimetic Activity
    • Barnett, G, Trisc, M, and Willette, R, Eds, pp, National Institute on Drug Abuse, Washington, DC
    • Anderson, G. M., Braun, G., Braun, U., Nichols, D. E., and Shulgin, A. T. (1978) Absolute Configuration and Psychotomimetic Activity, in Quasar Research Monograph 22 (Barnett, G., Trisc, M., and Willette, R., Eds.) pp 8-15, National Institute on Drug Abuse, Washington, DC.
    • (1978) Quasar Research Monograph , vol.22 , pp. 8-15
    • Anderson, G.M.1    Braun, G.2    Braun, U.3    Nichols, D.E.4    Shulgin, A.T.5
  • 25
    • 0024366246 scopus 로고
    • The effect of optical isomers of 3,4-methylenedioxymethamphetamine (MDMA) on stereotyped behavior in rats
    • Hiramatsu, M., Nabeshima, T., Kameyama, T., Maeda, Y., and Cho, A. K. (1989) The effect of optical isomers of 3,4-methylenedioxymethamphetamine (MDMA) on stereotyped behavior in rats. Pharmacol., Biochem. Behav. 33, 343-347.
    • (1989) Pharmacol., Biochem. Behav , vol.33 , pp. 343-347
    • Hiramatsu, M.1    Nabeshima, T.2    Kameyama, T.3    Maeda, Y.4    Cho, A.K.5
  • 27
    • 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, W. E., Godlewski, T., Karabenick, R. L., Stephens, J. M., Ullrich, T., Rice, K. C., and Woods, J. H. (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. Psychopharmacology 166, 202-211.
    • (2003) Psychopharmacology , 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
  • 28
    • 4143098459 scopus 로고    scopus 로고
    • Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine)
    • Pizarro, N., Farré, M., Pujadas, M., Peiro, A. M., Poset, P. N., Joglar, J., and de la Torre, R. (2004) Stereochemical analysis of 3,4-methylenedioxymethamphetamine and its main metabolites in human samples including the catechol-type metabolite (3,4-dihydroxymethamphetamine). Drug Metab. Dispos. 32, 1001-1007.
    • (2004) Drug Metab. Dispos , vol.32 , pp. 1001-1007
    • Pizarro, N.1    Farré, M.2    Pujadas, M.3    Peiro, A.M.4    Poset, P.N.5    Joglar, J.6    de la Torre, R.7
  • 29
    • 39749189410 scopus 로고    scopus 로고
    • In vivo pharmacology of MDMA and its enantiomers in rhesus monkeys
    • and references therein
    • Fantegrossi, W. E. (2008) In vivo pharmacology of MDMA and its enantiomers in rhesus monkeys. Exp. Clin. Psychopharmacol. 16, 1-12, and references therein.
    • (2008) Exp. Clin. Psychopharmacol , vol.16 , pp. 1-12
    • Fantegrossi, W.E.1
  • 30
    • 66749120158 scopus 로고    scopus 로고
    • Discriminative stimulus effects of MDMA and its enantiomers in mice: Pharmacokinetic considerations
    • Fantegrossi, W. E., Murai, N., Mathuna, B. O., Pizarro, N., and de la Torre, R. (2009) Discriminative stimulus effects of MDMA and its enantiomers in mice: pharmacokinetic considerations. J. Pharmacol. Exp. Ther. 329, 1006-1015.
    • (2009) J. Pharmacol. Exp. Ther , vol.329 , pp. 1006-1015
    • Fantegrossi, W.E.1    Murai, N.2    Mathuna, B.O.3    Pizarro, N.4    de la Torre, R.5
  • 31
    • 68949086185 scopus 로고    scopus 로고
    • Environmentally friendy expeditious one-pot electrochemical synthesis of bis-catechol-thioether metabolites of ecstasy: In vitro neurotoxic effects in the rat hippocampus
    • Felim, A., Neudörffer, A., Monnet, F. P., and Largeron, M. (2008) Environmentally friendy expeditious one-pot electrochemical synthesis of bis-catechol-thioether metabolites of ecstasy: in vitro neurotoxic effects in the rat hippocampus. Int. J. Electrochem. Sci. 3, 266-281.
    • (2008) Int. J. Electrochem. Sci , vol.3 , pp. 266-281
    • Felim, A.1    Neudörffer, A.2    Monnet, F.P.3    Largeron, M.4
  • 33
    • 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, J. (2002) 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, J.6
  • 34
    • 0342264746 scopus 로고    scopus 로고
    • + parent WP2 uvrA/pKM101: Detection of 31 oxidative mutagens
    • + parent WP2 uvrA/pKM101: detection of 31 oxidative mutagens. Mutat. Res. 467, 41-53.
    • (2000) Mutat. Res , vol.467 , pp. 41-53
    • Martínez, A.1    Urios, A.2    Blanco, M.3
  • 35
    • 0000607459 scopus 로고
    • Synthesis of some N-oxygenated products of 3,4-dimethoxyamphetamine and its N-alkyl derivatives
    • Morgan, P. H., and Beckett, A. H. (1975) Synthesis of some N-oxygenated products of 3,4-dimethoxyamphetamine and its N-alkyl derivatives. Tetrahedron 31, 2595-2601.
    • (1975) Tetrahedron , vol.31 , pp. 2595-2601
    • Morgan, P.H.1    Beckett, A.H.2
  • 36
  • 38
    • 33750209029 scopus 로고    scopus 로고
    • Synthesis and cytotoxic profile of 3,4-methylenedioxymethamphetamine ("ecstasy") and its metabolites on undifferentiated PC12 cells: A putative structure-toxicity relationship
    • Milhazes, N., Cunha-Oliveira, T., Martins, P., Garrido, J., Oliveira, C., Rego, A. C., and Borges, F. (2006) Synthesis and cytotoxic profile of 3,4-methylenedioxymethamphetamine ("ecstasy") and its metabolites on undifferentiated PC12 cells: a putative structure-toxicity relationship. Chem. Res. Toxicol. 19, 1294-1304.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 1294-1304
    • Milhazes, N.1    Cunha-Oliveira, T.2    Martins, P.3    Garrido, J.4    Oliveira, C.5    Rego, A.C.6    Borges, F.7
  • 39
    • 35948949906 scopus 로고    scopus 로고
    • X) of the benzylic position as a tunable synthesis of tetrahydroisoquinoline natural alkaloid analogues
    • X) of the benzylic position as a tunable synthesis of tetrahydroisoquinoline natural alkaloid analogues. Eur. J. Org. Chem. 5212-5225.
    • (2007) Eur. J. Org. Chem , pp. 5212-5225
    • Aubry, S.1    Pellet-Rostaing, S.2    Lemaire, M.3
  • 41
    • 33750080477 scopus 로고    scopus 로고
    • Synthesis and characterization of water-soluble and photostable L-DOPA dendrimers
    • Tang, S., Martinez, L. J., Sharma, A., and Chai, M. (2006) Synthesis and characterization of water-soluble and photostable L-DOPA dendrimers. Org. Lett. 8, 4421-4424.
    • (2006) Org. Lett , vol.8 , pp. 4421-4424
    • Tang, S.1    Martinez, L.J.2    Sharma, A.3    Chai, M.4
  • 42
    • 0026675653 scopus 로고    scopus 로고
    • 3 receptors. A promising antidiabetic and antiobesity agent. J. Med. Chem. 35, 3081-3084.
    • 3 receptors. A promising antidiabetic and antiobesity agent. J. Med. Chem. 35, 3081-3084.
  • 43
    • 28744436180 scopus 로고    scopus 로고
    • Diastereoselective intramolecular α-amidoalkylation reactions of L-DOPA derivatives. Asymmetric synthesis of pyrrolo[2,1-a]isoquinolines
    • Garcia, E., Arrasate, S., Lete, E., and Sotomayor, N. (2005) Diastereoselective intramolecular α-amidoalkylation reactions of L-DOPA derivatives. Asymmetric synthesis of pyrrolo[2,1-a]isoquinolines. J. Org. Chem. 70, 10368-10374.
    • (2005) J. Org. Chem , vol.70 , pp. 10368-10374
    • Garcia, E.1    Arrasate, S.2    Lete, E.3    Sotomayor, N.4
  • 44
    • 35948994629 scopus 로고
    • Synthesis and determination of the absolute stereochemistry of the enantiomers of 3-substituted 1,2,3,4-tetrahydroisoquinolines related to the calcium antagonist verapamil
    • Clark, R. D., Berger, J., Lee, C.-H., and Muchowski, J. M. (1987) Synthesis and determination of the absolute stereochemistry of the enantiomers of 3-substituted 1,2,3,4-tetrahydroisoquinolines related to the calcium antagonist verapamil. Heterocycles 26, 1290-1302.
    • (1987) Heterocycles , vol.26 , pp. 1290-1302
    • Clark, R.D.1    Berger, J.2    Lee, C.-H.3    Muchowski, J.M.4
  • 45
    • 0031036984 scopus 로고    scopus 로고
    • Cytometry in cell necrobiology: Analysis of apoptosis and accidental cell death (necrosis)
    • Darzynkiewicz, Z., Juan, G., Li, X., Gorczyca, W., Murakami, T., and Traganos, F. (1997) Cytometry in cell necrobiology: analysis of apoptosis and accidental cell death (necrosis). Cytometry 27, 1-20.
    • (1997) Cytometry , vol.27 , pp. 1-20
    • Darzynkiewicz, Z.1    Juan, G.2    Li, X.3    Gorczyca, W.4    Murakami, T.5    Traganos, F.6
  • 46
    • 0043173825 scopus 로고    scopus 로고
    • Dopamine induces autophagic cell death and α-synuclein increase in human neuroblastoma cells
    • Gomez-Santos, C., Ferrer, I., Santidrian, A. F., Barrachina, M., Gil, J., and Ambrioso, S. (2003) Dopamine induces autophagic cell death and α-synuclein increase in human neuroblastoma cells. J. Neurosci. Res. 73, 341-350.
    • (2003) J. Neurosci. Res , vol.73 , pp. 341-350
    • Gomez-Santos, C.1    Ferrer, I.2    Santidrian, A.F.3    Barrachina, M.4    Gil, J.5    Ambrioso, S.6
  • 47
    • 0037413452 scopus 로고    scopus 로고
    • Apoptosis-inducing neurotoxicity of dopamine and its metabolites via reactive quinone generation in neuroblastoma cells
    • Haque, M. E., Asanuma, M., Higashi, Y., Miyazaki, I., Tanaka, K.-I., and Ogawa, N. (2003) Apoptosis-inducing neurotoxicity of dopamine and its metabolites via reactive quinone generation in neuroblastoma cells. Biochim. Biophys. Acta 1619, 39-52.
    • (2003) Biochim. Biophys. Acta , vol.1619 , pp. 39-52
    • Haque, M.E.1    Asanuma, M.2    Higashi, Y.3    Miyazaki, I.4    Tanaka, K.-I.5    Ogawa, N.6
  • 48
    • 33644659245 scopus 로고    scopus 로고
    • A convenient approach for evaluating the toxicity profiles of in vitro neuroprotective alkylaminophenol derivatives
    • Urios, A., Largeron, M., Fleury, M.-B., and Blanco, M. (2006) A convenient approach for evaluating the toxicity profiles of in vitro neuroprotective alkylaminophenol derivatives. Free Radical Biol. Med. 40, 791-800.
    • (2006) Free Radical Biol. Med , vol.40 , pp. 791-800
    • Urios, A.1    Largeron, M.2    Fleury, M.-B.3    Blanco, M.4
  • 50
    • 67449103235 scopus 로고    scopus 로고
    • Enantioselectivity in the methylation of the catecholic phase I metabolites of methylenedioxy designer drugs and their capability to inhibit catechol-O-methyltransferase-catalyzed dopamine 3-methylation
    • Meyer, M. R., and Maurer, H. H. (2009) Enantioselectivity in the methylation of the catecholic phase I metabolites of methylenedioxy designer drugs and their capability to inhibit catechol-O-methyltransferase-catalyzed dopamine 3-methylation. Chem. Res. Toxicol. 22, 1205-1211.
    • (2009) Chem. Res. Toxicol , vol.22 , pp. 1205-1211
    • Meyer, M.R.1    Maurer, H.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.