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Chemical Compound Review

MDMA     1-benzo[1,3]dioxol-5-yl-N- methyl-propan-2...

Synonyms: Ecstasy, CHEMBL43048, SureCN44210, CCRIS 9277, CHEBI:1391, ...
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Disease relevance of Methylenedioxymethamphetamine

  • In three patients, MDMA or MDEA may have contributed to death by the induction of arrhythmias in individuals with underlying natural disease [1].
  • There has been a recent increase in cases of severe toxicity following recreational misuse of small amounts of MDMA [2].
  • Hyperpyrexia and rhabdomyolysis after MDMA ("ecstasy") abuse [3].
  • In addition, we have monitored 7 cases of hepatotoxicity and suspect that the frequency of this complication is increasing; a history of MDMA misuse should be sought in young people presenting with unexplained jaundice or hepatomegaly [2].
  • Oral MDMA (0.5 and 1.5 mg/kg of body weight) or placebo was administered 1 hour before echocardiographic measurements in three weekly sessions [4].

Psychiatry related information on Methylenedioxymethamphetamine

  • The widely abused amphetamine analog 3,4-methylenedioxymethamphetamine (MDMA, also called "ecstasy") induces hallucination and psychostimulation, as well as long-term neuropsychiatric behaviors such as panic and psychosis [5].
  • RESULTS: The MDMA users recalled significantly fewer words than control subjects on delayed (p =.03) but not immediate recall (p =.08) [6].
  • METHODS: An auditory verbal memory task (Rey Auditory Verbal Learning Test) was used to study eight abstinent MDMA users and seven control subjects [6].
  • MDMA ("ecstasy") and panic disorder: induction by a single dose [7].
  • MDMA produced a widespread decrease of slow and medium frequency activity and an increase of fast frequency activity in the anterior temporal and posterior orbital cortex, concomitant with a marked enhancement of mood, emotional arousal and increased extraversion [8].

High impact information on Methylenedioxymethamphetamine


Chemical compound and disease context of Methylenedioxymethamphetamine


Biological context of Methylenedioxymethamphetamine


Anatomical context of Methylenedioxymethamphetamine


Associations of Methylenedioxymethamphetamine with other chemical compounds


Gene context of Methylenedioxymethamphetamine

  • In contrast, CORT responses in MDMA users were restored after 12 months of abstinence, with significantly higher responses to D-fen, in comparison with 3-week responses (p < .05) [26].
  • We have previously shown that MDMA or 5-HT1A/1B receptor agonist RU24969 fails to stimulate locomotor activity in 5-HT1B receptor-null mice [27].
  • We examined whether a systemic MDMA injection would reduce the physiological drive to eat in starved mice and tested if the inactivation of 5-HT1B or 5-HT2C receptors could restore this response [27].
  • MDMA metabolism is regulated by the levels of CYP2D6 and COMT (both exhibit some genetic polymorphism), and range of activity of these enzymes may account for some inter-individual differences in terms of toxic responses to the drug [28].
  • OBJECTIVES: To clarify whether SERT-selective effects of MDMA at human monoamine transporters can account for the reported MDMA-induced selective toxicity of serotonin neurons in primate brain [29].

Analytical, diagnostic and therapeutic context of Methylenedioxymethamphetamine


  1. 'Eve' and 'Ecstasy'. A report of five deaths associated with the use of MDEA and MDMA. Dowling, G.P., McDonough, E.T., Bost, R.O. JAMA (1987) [Pubmed]
  2. Toxicity and deaths from 3,4-methylenedioxymethamphetamine ("ecstasy"). Henry, J.A., Jeffreys, K.J., Dawling, S. Lancet (1992) [Pubmed]
  3. Hyperpyrexia and rhabdomyolysis after MDMA ("ecstasy") abuse. Screaton, G.R., Singer, M., Cairns, H.S., Thrasher, A., Sarner, M., Cohen, S.L. Lancet (1992) [Pubmed]
  4. Cardiovascular effects of 3,4-methylenedioxymethamphetamine. A double-blind, placebo-controlled trial. Lester, S.J., Baggott, M., Welm, S., Schiller, N.B., Jones, R.T., Foster, E., Mendelson, J. Ann. Intern. Med. (2000) [Pubmed]
  5. The abused drug MDMA (Ecstasy) induces programmed death of human serotonergic cells. Simantov, R., Tauber, M. FASEB J. (1997) [Pubmed]
  6. Prefrontal N-acetylaspartate is strongly associated with memory performance in (abstinent) ecstasy users: preliminary report. Reneman, L., Majoie, C.B., Schmand, B., van den Brink, W., den Heeten, G.J. Biol. Psychiatry (2001) [Pubmed]
  7. MDMA ("ecstasy") and panic disorder: induction by a single dose. McCann, U.D., Ricaurte, G.A. Biol. Psychiatry (1992) [Pubmed]
  8. Localization of MDMA-induced brain activity in healthy volunteers using low resolution brain electromagnetic tomography (LORETA). Frei, E., Gamma, A., Pascual-Marqui, R., Lehmann, D., Hell, D., Vollenweider, F.X. Human brain mapping. (2001) [Pubmed]
  9. The pharmacology and clinical pharmacology of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy"). Green, A.R., Mechan, A.O., Elliott, J.M., O'Shea, E., Colado, M.I. Pharmacol. Rev. (2003) [Pubmed]
  10. New insights into the mechanism of action of amphetamines. Fleckenstein, A.E., Volz, T.J., Riddle, E.L., Gibb, J.W., Hanson, G.R. Annu. Rev. Pharmacol. Toxicol. (2007) [Pubmed]
  11. (+/-)3,4-Methylenedioxymethamphetamine selectively damages central serotonergic neurons in nonhuman primates. Ricaurte, G.A., Forno, L.S., Wilson, M.A., DeLanney, L.E., Irwin, I., Molliver, M.E., Langston, J.W. JAMA (1988) [Pubmed]
  12. Is frequent dosing with ecstasy a risky business for dopamine-containing neurons? O'Shea, E., Colado, M.I. Trends Pharmacol. Sci. (2003) [Pubmed]
  13. 3,4-Methylenedioxymethamphetamine increases interleukin-1beta levels and activates microglia in rat brain: studies on the relationship with acute hyperthermia and 5-HT depletion. Orio, L., O'Shea, E., Sanchez, V., Pradillo, J.M., Escobedo, I., Camarero, J., Moro, M.A., Green, A.R., Colado, M.I. J. Neurochem. (2004) [Pubmed]
  14. Ethanol, 3,4-methylenedioxymethamphetamine (ecstasy) and their combination: long-term behavioral, neurochemical and neuropharmacological effects in the rat. Cassel, J.C., Riegert, C., Rutz, S., Koenig, J., Rothmaier, K., Cosquer, B., Lazarus, C., Birthelmer, A., Jeltsch, H., Jones, B.C., Jackisch, R. Neuropsychopharmacology (2005) [Pubmed]
  15. Chronic fluoxetine treatment partly attenuates the long-term anxiety and depressive symptoms induced by MDMA ('Ecstasy') in rats. Thompson, M.R., Li, K.M., Clemens, K.J., Gurtman, C.G., Hunt, G.E., Cornish, J.L., McGregor, I.S. Neuropsychopharmacology (2004) [Pubmed]
  16. Effects of dose, sex, and long-term abstention from use on toxic effects of MDMA (ecstasy) on brain serotonin neurons. Reneman, L., Booij, J., de Bruin, K., Reitsma, J.B., de Wolff, F.A., Gunning, W.B., den Heeten, G.J., van den Brink, W. Lancet (2001) [Pubmed]
  17. Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans. de la Torre, R., Farré, M. Trends Pharmacol. Sci. (2004) [Pubmed]
  18. The effects of methylenedioxymethamphetamine (MDMA, "Ecstasy") on monoaminergic neurotransmission in the central nervous system. White, S.R., Obradovic, T., Imel, K.M., Wheaton, M.J. Prog. Neurobiol. (1996) [Pubmed]
  19. Methylenedioxyamphetamine (MDA) and methylenedioxymethamphetamine (MDMA) cause selective ablation of serotonergic axon terminals in forebrain: immunocytochemical evidence for neurotoxicity. O'Hearn, E., Battaglia, G., De Souza, E.B., Kuhar, M.J., Molliver, M.E. J. Neurosci. (1988) [Pubmed]
  20. Neuroendocrine and mood responses to intravenous L-tryptophan in 3,4-methylenedioxymethamphetamine (MDMA) users. Preliminary observations. Price, L.H., Ricaurte, G.A., Krystal, J.H., Heninger, G.R. Arch. Gen. Psychiatry (1989) [Pubmed]
  21. Mechanisms of neurotransmitter release by amphetamines: a review. Sulzer, D., Sonders, M.S., Poulsen, N.W., Galli, A. Prog. Neurobiol. (2005) [Pubmed]
  22. Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons. Stumm, G., Schlegel, J., Schäfer, T., Würz, C., Mennel, H.D., Krieg, J.C., Vedder, H. FASEB J. (1999) [Pubmed]
  23. Memory impairment in abstinent MDMA ("Ecstasy") users. Bolla, K.I., McCann, U.D., Ricaurte, G.A. Neurology (1998) [Pubmed]
  24. Prior exposure to chronic stress and MDMA potentiates mesoaccumbens dopamine release mediated by the 5-HT(1B) receptor. Amato, J.L., Bankson, M.G., Yamamoto, B.K. Neuropsychopharmacology (2007) [Pubmed]
  25. Dissociation of the neurochemical and behavioral toxicology of MDMA ('Ecstasy') by citalopram. Piper, B.J., Fraiman, J.B., Owens, C.B., Ali, S.F., Meyer, J.S. Neuropsychopharmacology (2008) [Pubmed]
  26. Long-lasting effects of (+/-)3,4-methylenedioxymethamphetamine (ecstasy) on serotonin system function in humans. Gerra, G., Zaimovic, A., Ferri, M., Zambelli, U., Timpano, M., Neri, E., Marzocchi, G.F., Delsignore, R., Brambilla, F. Biol. Psychiatry (2000) [Pubmed]
  27. 3,4-N-methlenedioxymethamphetamine-induced hypophagia is maintained in 5-HT1B receptor knockout mice, but suppressed by the 5-HT2C receptor antagonist RS102221. Conductier, G., Crosson, C., Hen, R., Bockaert, J., Compan, V. Neuropsychopharmacology (2005) [Pubmed]
  28. A bitter pill. Overview of ecstasy (MDMA, MDA) related fatalities. Schifano, F. Psychopharmacology (Berl.) (2004) [Pubmed]
  29. MDMA (Ecstasy) and human dopamine, norepinephrine, and serotonin transporters: implications for MDMA-induced neurotoxicity and treatment. Verrico, C.D., Miller, G.M., Madras, B.K. Psychopharmacology (Berl.) (2007) [Pubmed]
  30. Positron emission tomographic evidence of toxic effect of MDMA ("Ecstasy") on brain serotonin neurons in human beings. McCann, U.D., Szabo, Z., Scheffel, U., Dannals, R.F., Ricaurte, G.A. Lancet (1998) [Pubmed]
  31. Positron emission tomography findings in heavy users of MDMA. Holland, J. Lancet (1999) [Pubmed]
  32. Graft dysfunction mimicking autoimmune hepatitis following liver transplantation in adults. Heneghan, M.A., Portmann, B.C., Norris, S.M., Williams, R., Muiesan, P., Rela, M., Heaton, N.D., O'Grady, J.G. Hepatology (2001) [Pubmed]
  33. Brain hyperthermia as physiological and pathological phenomena. Kiyatkin, E.A. Brain Res. Brain Res. Rev. (2005) [Pubmed]
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