(±)-3,4-methylenedioxymethamphetamine and metabolite disposition in plasma and striatum of wild-type and multidrug resistance protein 1a knock-out mice

Journal of Analytical Toxicology

Volumn 35, Issue 7, 2011, Pages 470-480

  Scheidweiler, Karl B ^a   Ladenheim, Bruce ^a   Barnes, Allan J ^a   Cadet, Jean Lud ^a   Huestis, Marilyn A ^a  

^a NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 O METHYL ALPHA METHYLDOPAMINE; 3,4 METHYLENEDIOXYMETHAMPHETAMINE; 4 HYDROXY 3 METHOXYMETHAMPHETAMINE; DRUG METABOLITE; MULTIDRUG RESISTANCE PROTEIN 1; MULTIDRUG RESISTANCE PROTEIN 1A; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; BRAIN LEVEL; CONTROLLED STUDY; CORPUS STRIATUM; KNOCKOUT MOUSE; LIVER METABOLISM; MALE; MASS FRAGMENTOGRAPHY; MAXIMUM PLASMA CONCENTRATION; MOUSE; NEUROPROTECTION; NEUROTOXICITY; NONHUMAN; WILD TYPE;

MURINAE; MUS;

EID: 80052644573     PISSN: 01464760     EISSN: 19452403     Source Type: Journal    
DOI: 10.1093/anatox/35.7.470     Document Type: Article

References (47)

1. J. Morton. Ecstasy: pharmacology and neurotoxicity. Curr. Opin. Pharmacol. 5: 79-86 (2005).
2. J.P. Capela, H. Carmo, F. Remiao, M.L. Bastos, A. Meisel, and F. Carvalho. Molecular and cellular mechanisms of ecstasy-induced neurotoxicity: an overview. Mol. Neurobiol. 39: 210-271 (2009).
3. E. Gouzoulis-Mayfrank and J. Daumann. Neurotoxicity of methylenedioxyamphetamines (MDMA; ecstasy) in humans: how strong is the evidence for persistent brain damage? Addiction 101: 348-361 (2006).
4. R. Thomasius, P. Zapletalova, K. Petersen, R. Buchert, B. Andresen, L.Wartberg, B. Nebeling, and A. Schmoldt. Mood, cognition and serotonin transporter availability in current and former ecstasy (MDMA) users: the longitudinal perspective. J. Psychopharmacol. 20: 211-225 (2006).
5. S.N. Karlsen, O. Spigset, and L. Slordal. The dark side of ecstasy: neuropsychiatric symptoms after exposure to 3,4-methylenedioxymethamphetamine. Basic Clin. Pharmacol. Toxicol. 102: 15-24 (2008).
6. R.H. Ho and R.B. Kim. Transporters and drug therapy: implications for drug disposition and disease. Clin. Pharmacol. Ther. 78: 260-277 (2005).
7. F.J. Sharom. ABC multidrug transporters: structure, function and role in chemoresistance. Pharmacogenomics 9: 105-127 (2008).
8. K.B. Scheidweiler, B. Ladenheim, J.L. Cadet, and M.A. Huestis. Mice lacking multidrug resistance protein 1a show altered dopaminergic responses to methylenedioxymethamphetamine (MDMA) in striatum. Neurotox. Res. 18: 200-209 (2010).
9. H. Mann, B. Ladenheim, H. Hirata, T.H. Moran, and J.L. Cadet. Differential toxic effects of methamphetamine (METH) and methylenedioxymethamphetamine (MDMA) in multidrug-resistant (mdr1a) knockout mice. Brain Res. 769: 340-346 (1997).
10. V.V. Upreti and N.D. Eddington. Fluoxetine pretreatment effects pharmacokinetics of 3,4-methylenedioxymethamphetamine (MDMA, ECSTASY) in rat. J. Pharm. Sci. 97: 1593-1605 (2008).
11. T.J. Monks, D.C. Jones, F. Bai, and S.S. Lau. The role of metabolism in 3,4-(+)-methylenedioxyamphetamine and 3,4-(+)-methylenedioxymethamphetamine (ecstasy) toxicity. Ther. Drug Monit. 26: 132-136 (2004).
12. T. Kraemer and H.H. Maurer. Toxicokinetics of amphetamines: metabolism and toxicokinetic data of designer drugs, amphetamine, methamphetamine, and their N-alkyl derivatives. Ther. Drug Monit. 24: 277-289 (2002).
13. R. de la Torre, M. Farré, M. Navarro, R. Pacifici, P. Zuccaro, and S. Pichini. Clinical pharmacokinetics of amfetamine and related substances: monitoring in conventional and non-conventional matrices. Clin. Pharmacokinet. 43: 157-185 (2004).
14. R. de la Torre, M. Farré, J. Ortuño, M. Mas, R. Brenneisen, P.N. Roset, J. Segura, and J. Camí. Non-linear pharmacokinetics of MDMA ('ecstasy') in humans. Br. J. Clin. Pharmacol. 49: 104-109 (2000).
15. E.A. Kolbrich, R.S. Goodwin, D.A. Gorelick, R.J. Hayes, E.A. Stein, and M.A. Huestis. Plasma pharmacokinetics of 3,4-methylenedioxymethamphetamine after controlled oral administration to young adults. Ther. Drug Monit. 30: 320-332 (2008).
16. M. Mueller, F.T. Peters, H.H. Maurer, U.D. McCann, and G.A. Ricaurte. Non-linear pharmacokinetics of MDMA ("Ecstasy") and its major metabolites in squirrel monkeys at plasma concentrations of MDMA that develop after typical psychoactive doses. J. Pharmacol. Exp. Ther. 327(1): 38-44 (2008).
17. T. Chu, Y. Kumagai, E.W. DiStefano, and A.K. Cho. Disposition of methylenedioxymethamphetamine and three metabolites in the brains of different rat strains and their possible roles in acute serotonin depletion. Biochem. Pharmacol. 51: 789-796 (1996).
18. M.H. Baumann, D. Zolkowska, I. Kim, K.B. Scheidweiler, R.B. Rothman, and M.A. Huestis. Effects of dose and route of administration on pharmacokinetics of (+ or -)-3,4-methylenedioxymethamphetamine in the rat. Drug Metab. Dispos. 37: 2163-2170 (2009).
19. A. Heydari, K.R. Yeo, M.S. Lennard, S.W. Ellis, G.T. Tucker, and A. Rostami-Hodjegan. Mechanism-based inactivation of CYP2D6 by methylenedioxymethamphetamine. Drug Metab. Dispos. 32: 1213-1217 (2004).
20. M. Mueller, J. Yuan, A. Felim, A. Neudorffer, F.T. Peters, H.H. Maurer, U.D. McCann, M. Largeron, and G.A. Ricaurte. Further studies on the role of metabolites in (+/-)-3,4-methylenedioxymethamphetamine- induced serotonergic neurotoxicity. Drug Metab. Dispos. 37: 2079-2086 (2009).
21. H.K. Lim, S. Zeng, D.M. Chei, and R.L. Foltz. Comparative investigation of disposition of 3,4-(methylenedioxy)methamphetamine (MDMA) in the rat and the mouse by a capillary gas chromatography-mass spectrometry assay based on perfluorotributylamine-enhanced ammonia positive ion chemical ionization. J. Pharm. Biomed. Anal. 10: 657-665 (1992).
22. R. de la Torre and M. Farre. Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. Trends Pharmacol. Sci. 25: 505-508 (2004).
23. A.R. Green, J. Gabrielsson, C.A. Marsden, and K.C. Fone. MDMA: on the translation from rodent to human dosing. Psychopharmacol. (Berl). 204: 375-378 (2009).
24. I. Escobedo, E. O'Shea, L. Orio, V. Sanchez, M. Segura, R. de la Torre, M. Farré A.R. Green, and M.I. Colado. A comparative study on the acute and long-term effects of MDMA and 3,4-dihydroxymethamphetamine (HHMA) on brain monoamine levels after i.p. or striatal administration in mice. Br. J. Pharmacol. 144: 231-241 (2005).
25. W.E. Fantegrossi, N. Murai, B.O. Mathuna, N. Pizarro, and R. de la Torre. Discriminative stimulus effects of 3,4-methylenedioxymethamphetamine and its enantiomers in mice: pharmacokinetic considerations. J. Pharmacol. Exp. Ther. 329: 1006-1015 (2009).
26. K.B. Scheidweiler, A.J. Barnes, and M.A. Huestis. A validated gas chromatographic-electron impact ionization mass spectrometric method for methamphetamine, methylenedioxymethamphetamine (MDMA), and metabolites in mouse plasma and brain. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 876: 266-276 (2008).
27. A.J. Bailer. Testing for the equality of area under the curves when using destructive measurement techniques. J. Pharmacokinet. Biopharm. 16: 303-309 (1988).
28. M. Sanchez-Carbayo, T.J. Belbin, K. Scotlandi, M. Prystowsky, N. Baldini, G. Childs, and C. Cordon-Cardo. Expression profiling of osteosarcoma cells transfected with MDR1 and NEO genes: regulation of cell adhesion, apoptosis, and tumor suppressionrelated genes. Lab. Invest. 83: 507-517 (2003).
29. D.C. Jones, C. Duvauchelle, A. Ikegami, C.M. Olsen, S.S. Lau, R. de la Torre, and T.J. Monks. Serotonergic neurotoxic metabolites of ecstasy identified in rat brain. J. Pharmacol. Exp. Ther. 313: 422-431 (2005).
30. G.V. Erives, S.S. Lau, and T.J. Monks. Accumulation of neurotoxic thioether metabolites of 3,4-(+/-)-methylenedioxymethamphetamine in rat brain. J. Pharmacol. Exp. Ther. 324: 284-291 (2008).
31. D.C. Jones, S.S. Lau, and T.J. Monks. Thioether metabolites of 3,4-methylenedioxyamphetamine and 3,4-methylenedioxymethamphetamine inhibit human serotonin transporter (hSERT) function and simultaneously stimulate dopamine uptake into hSERTexpressing SK-N-MC cells. J. Pharmacol. Exp. Ther. 311: 298-306 (2004).
32. F. Bai, S.S. Lau, and T.J. Monks. Glutathione and N-acetylcysteine conjugates of alpha-methyldopamine produce serotonergic neurotoxicity: possible role in methylenedioxyamphetamine-mediated neurotoxicity. Chem. Res. Toxicol. 12: 1150-1157 (1999).
33. R.T. Miller, S.S. Lau, and T.J. Monks. Effects of intracerebroventricular administration of 5-(glutathion-S-yl)-alphamethyldopamine on brain dopamine, serotonin, and norepinephrine concentrations in male Sprague-Dawley rats. Chem. Res. Toxicol. 9: 457-465 (1996).
34. N. Ketabi-Kiyanvash, J.Weiss,W. E. Haefeli, and G. Mikus. P-Glycoprotein modulation by the designer drugs methylenedioxymethamphetamine, methylenedioxyethylamphetamine and paramethoxyamphetamine. Addict Biol. 8: 413-418 (2003).
35. K.M. Bertelsen, D.J. Greenblatt, and L.L. von Moltke. Apparent active transport of MDMA is not mediated by P-glycoprotein: a comparison with MDCK and Caco-2 monolayers. Biopharm. Drug Dispos. 27: 219-227 (2006).
36. A. Crowe and S. Diep. pH dependent efflux of methamphetamine derivatives and their reversal through human Caco-2 cell monolayers. Eur. J. Pharmacol. 592: 7-12 (2008).
37. E.G. Schuetz, D.R. Umbenhauer, K.Yasuda, C. Brimer, L. Nguyen, M.V. Relling, J.D. Schuetz, and A.H. Schinkel. Altered expression of hepatic cytochromes P-450 in mice deficient in one or more mdr1 genes. Mol. Pharmacol. 57: 188-197 (2000).
38. S.O. Pirnay, T.T. Abraham, R.H. Lowe, and M.A. Huestis. Selection and optimization of hydrolysis conditions for the quantification of urinary metabolites of MDMA. J. Anal. Toxicol. 30: 563-569 (2006).
39. M. Mueller, E.A. Kolbrich-Spargo, F. T. Peters, M.A. Huestis, G.A. Ricaurte, and H.H. Maurer. Hydrolysis of 3,4-methylenedioxymethamphetamine (MDMA) metabolite conjugates in human, squirrel monkey, and rat plasma. Anal. Bioanal. Chem. 393: 1607-1617 (2009).
40. N. Shima,M. Katagi, H. Kamata, K. Zaitsu,T. Kamata, M. Nishikawa, A. Miki, H. Tsuchihashi, T. Sakuma, and N. Nemoto. Urinary excretion of the main metabolites of 3,4-methylenedioxymethamphetamine (MDMA), including the sulfate and glucuronide of 4-hydroxy-3-methoxymethamphetamine (HMMA), in humans and rats. Xenobiotica 38: 314-324 (2008).
41. M. Mas, M. Farré, R. de la Torre, P.N. Roset, J. Ortuño, J. Segura, and J. Camí. Cardiovascular and neuroendocrine effects and pharmacokinetics of 3,4-methylenedioxymethamphetamine in humans. J. Pharmacol. Exp. Ther. 290: 136-145 (1999).
42. M. Farré, R. de la Torre, B.O. Mathúna, P.N. Roset, A.M. Peiró, M. Torrens, J. Ortuño M. Pujadas, and J. Camí. Repeated doses administration of MDMA in humans: pharmacological effects and pharmacokinetics. Psychopharmacology (Berl). 173: 364-375 (2004).
43. N. Pizarro, M. Farre, M. Pujadas, A.M. Peiro, P.N. Roset, J. Joglar, and R. de la Torre. 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).
44. R. de la Torre, M. Farre, B.O. Mathuna, P.N. Roset, N. Pizarro, M. Segura, M. Torrens, J. Ortuno, M. Pujadas, and J. Cami. MDMA (ecstasy) pharmacokinetics in a CYP2D6 poor metaboliser and in nine CYP2D6 extensive metabolisers. Eur. J. Clin. Pharmacol. 61: 551-554 (2005).
45. M. Mueller, E.A. Kolbrich, F.T. Peters, H.H. Maurer, U.D. McCann, M.A. Huestis, and G.A. Ricaurte. Direct comparison of (+/-) 3,4- methylenedioxymethamphetamine ("ecstasy") disposition and metabolism in squirrel monkeys and humans. Ther. Drug Monit. 31: 367-373 (2009).
46. E.A. De Letter, K.M. Clauwaert, W.E. Lambert, J.F. Van Bocxlaer, A.P. De Leenheer, and M.H. Piette. Distribution study of 3,4-methylenedioxymethamphetamine and 3,4-methylenedioxyamphetamine in a fatal overdose. J. Anal. Toxicol. 26: 113-118 (2002).
47. D.Wu, S.V. Otton, T. Inaba,W. Kalow, and E.M. Sellers. Interactions of amphetamine analogs with human liver CYP2D6. Biochem. Pharmacol. 53: 1605-1612 (1997).