The Pharmacology and Clinical Pharmacology of 3,4-Methylenedioxymethamphetamine (MDMA, “Ecstasy”)

Green, A. Richard; Mechan, Annis O.; Elliott, J. Martin; O’Shea, Esther; Colado, M. Isabel

doi:10.1124/pr.55.3.3

Cited by 1,272Psychedelics and Drug StudiesNeurotransmitter Receptor Influence on BehaviorForensic Toxicology and Drug Analysis

The Pharmacology and Clinical Pharmacology of 3,4-Methylenedioxymethamphetamine (MDMA, “Ecstasy”)

Green, A. Richard, Mechan, Annis O., Elliott, J. Martin, O’Shea, Esther, Colado, M. Isabel·2003·Pharmacological Reviews

DOI 10.1124/pr.55.3.3

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Abstract

The amphetamine derivative (+/-)-3,4-methylenedioxymethamphetamine (MDMA, ecstasy) is a popular recreational drug among young people, particularly those involved in the dance culture. MDMA produces an acute, rapid enhancement in the release of both serotonin (5-HT) and dopamine from nerve endings in the brains of experimental animals. It produces increased locomotor activity and the serotonin behavioral syndrome in rats. Crucially, it produces dose-dependent hyperthermia that is potentially fatal in rodents, primates, and humans. Some recovery of 5-HT stores can be seen within 24 h of MDMA administration. However, cerebral 5-HT concentrations then decline due to specific neurotoxic damage to 5-HT nerve endings in the forebrain. This neurodegeneration, which has been demonstrated both biochemically and histologically, lasts for months in rats and years in primates. In general, other neurotransmitters appear unaffected. In contrast, MDMA produces a selective long-term loss of dopamine nerve endings in mice. Studies on the mechanisms involved in the neurotoxicity in both rats and mice implicate the formation of tissue-damaging free radicals. Increased free radical formation may result from the further breakdown of MDMA metabolic products. Evidence for the occurrence of MDMA-induced neurotoxic damage in human users remains equivocal, although some biochemical and functional data suggest that damage may occur in the brains of heavy users. There is also some evidence for long-term physiological and psychological changes occurring in human recreational users. However, such evidence is complicated by the lack of knowledge of doses ingested and the fact that many subjects studied are or have been poly-drug users.

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MDMA's acute pharmacodynamic actions include carrier-mediated release of 5-HT from presynaptic vesicles and monoamine oxidase inhibition, causing rapid rises in extracellular 5-HT.
“MDMA’s acute pharmacodynamic actions include carrier-mediated release of 5-HT from presynaptic vesicles and monoamine oxidase inhibition, resulting in sudden increases in extracellular 5-HT levels (for review, see Green et al. 2003).”
From Effects of MDMA on sociability and neural response to social threat and social reward (2009) · cites this paper as Green et al. 2003

2 retracted

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The spin trap reagent α-phenyl-N-tert-butylnitrone prevents ‘ecstasy’-induced neurodegeneration of 5-hydroxytryptamine neurones
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Involvement of the serotonin transporter in the formation of hydroxyl radicals induced by 3,4-methylenedioxymethamphetamine
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FACTORS INFLUENCING THE TOXICITY OF SYMPATHOMIMETIC AMINES TO SOLITARY MICE
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Mitochondrial superoxide: production, biological effects, and activation of uncoupling proteins
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Designer drugs: mechanism of action and adverse effects
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Hallucinogens in Mental Health: Preclinical and Clinical Studies on LSD, Psilocybin, MDMA, and Ketamine
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N-Substituted Piperazines Abused by Humans Mimic the Molecular Mechanism of 3,4-Methylenedioxymethamphetamine (MDMA, or ‘Ecstasy’)
Baumann, M. H., Clark, R. D., BUDZYNSKI, A. G., Partilla, J. S., Blough, B. E., & Rothman, R. B. (2004) · Neuropsychopharmacology · doi:10.1038/sj.npp.1300585 · Cited by 248 · see citing works
Increasing MDMA use among college students: results of a national survey
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The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain
Nagai, F., Nonaka, R., & Satoh Hisashi Kamimura, K. (2007) · European Journal of Pharmacology · doi:10.1016/j.ejphar.2006.11.075 · Cited by 279 · see citing works
Chronic tolerance to recreational MDMA (3,4-methylenedioxymethamphetamine) or Ecstasy
Parrott, A. C. (2005) · Journal of Psychopharmacology · doi:10.1177/0269881105048900 · Cited by 238 · see citing works
Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity
Parrott, A. C. (2004) · Psychopharmacology · doi:10.1007/s00213-003-1712-7 · Cited by 232 · see citing works
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Amphetamine-related drugs neurotoxicity in humans and in experimental animals: Main mechanisms
Moratalla, R., Khairnar, A., Simola, N., Granado, N., García-Montes, J. R., Porceddu, P. F., Tizabi, Y., Costa, G., & Morelli, M. (2015) · Progress in Neurobiology · doi:10.1016/j.pneurobio.2015.09.011 · Cited by 225 · see citing works
Effects of MDMA on sociability and neural response to social threat and social reward
Bedi, G., Phan, K. L., Angstadt, M., & de Wit, H. (2009) · Psychopharmacology · doi:10.1007/s00213-009-1635-z · Cited by 206 · see citing works
Differential pharmacological in vitro properties of organic cation transporters and regional distribution in rat brain.
Amphoux, A., Vialou, V., Drescher, E., Brüss, M., la Cour, C., Rochat, C., Millan, M., Giros, B., Bönisch, H., & Gautron, S. (2006) · Neuropharmacology · doi:10.1016/j.neuropharm.2006.01.005 · Cited by 219 · see citing works
Neuropathology of substance use disorders
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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. (2005) · Psychopharmacology · doi:10.1007/s00213-005-0174-5 · Cited by 205 · see citing works
Quantitative PET Studies of the Serotonin Transporter in MDMA Users and Controls Using [11C]McN5652 and [11C]DASB
McCann, U. D., Szabó, Z. R., Seckin, E., Rosenblatt, P., Mathews, W. B., Ravert, H. T., Dannals, R. F., & Ricaurte, G. A. (2005) · Neuropsychopharmacology · doi:10.1038/sj.npp.1300736 · Cited by 204 · see citing works
Methylenedioxymethamphetamine (MDMA, Ecstasy) neurotoxicity: cellular and molecular mechanisms
Lyles, J., & Cadet, J. L. (2003) · Brain Research Reviews · doi:10.1016/s0165-0173(03)00173-5 · Cited by 199 · see citing works
The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents*
Freudenmann, R. W., Öxler, F., & Bernschneider‐Reif, S. (2006) · Addiction · doi:10.1111/j.1360-0443.2006.01511.x · Cited by 198 · see citing works
Brain temperature homeostasis: physiological fluctuations and pathological shifts
Kiyatkin, E. A. (2009) · Frontiers in bioscience · doi:10.2741/3608 · Cited by 197 · see citing works
Neurotoxicity of MDMA (ecstasy): the limitations of scaling from animals to humans
de la Torre, R., & Farré, M. (2004) · Trends in Pharmacological Sciences · doi:10.1016/j.tips.2004.08.001 · Cited by 192 · see citing works
Altered states: the clinical effects of Ecstasy
Cole, J. C., & Sumnall, H. R. (2003) · Pharmacology & Therapeutics · doi:10.1016/s0163-7258(03)00003-2 · Cited by 190 · see citing works
Neurotoxicity of methylenedioxyamphetamines (MDMA; ecstasy) in humans: how strong is the evidence for persistent brain damage?
Gouzoulis‐Mayfrank, E., & Daumann, J. (2006) · Addiction · doi:10.1111/j.1360-0443.2006.01314.x · Cited by 189 · see citing works
Causes and consequences of methamphetamine and MDMA toxicity
Quinton, M. S., & Yamamoto, B. K. (2006) · The AAPS Journal · doi:10.1007/bf02854904 · Cited by 188 · see citing works
Contributions of serotonin in addiction vulnerability
Kirby, L. G., Zeeb, F. D., & Winstanley, C. A. (2011) · Neuropharmacology · doi:10.1016/j.neuropharm.2011.03.022 · Cited by 183 · see citing works
Human psychobiology of MDMA or ‘Ecstasy’: an overview of 25 years of empirical research
Parrott, A. C. (2013) · Human Psychopharmacology Clinical and Experimental · doi:10.1002/hup.2318 · Cited by 185 · see citing works
A critical inquiry into marble-burying as a preclinical screening paradigm of relevance for anxiety and obsessive–compulsive disorder: Mapping the way forward
de Brouwer, G., Fick, A., Harvey, B. H., & Wolmarans, D. W. (2018) · Cognitive Affective & Behavioral Neuroscience · doi:10.3758/s13415-018-00653-4 · Cited by 188 · see citing works
A review of the mechanisms involved in the acute MDMA (ecstasy)-induced hyperthermic response
Green, A. R., O’Shea, E., & Colado, M. I. (2004) · European Journal of Pharmacology · doi:10.1016/j.ejphar.2004.07.006 · Cited by 181 · see citing works
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A bitter pill. Overview of ecstasy (MDMA, MDA) related fatalities
Schifano, F. (2004) · Psychopharmacology · doi:10.1007/s00213-003-1730-5 · Cited by 181 · see citing works
The confounding problem of polydrug use in recreational ecstasy/MDMA users: a brief overview
Gouzoulis‐Mayfrank, E., & Daumann, J. (2006) · Journal of Psychopharmacology · doi:10.1177/0269881106059939 · Cited by 179 · see citing works
The Effects of Acute Dopamine Reuptake Inhibition on Performance
Roelands, B., Hasegawa, H., Watson, P., Piacentini, M. F., Buyse, L., Schutter, G. D., & MEEUSEN, R. R. (2008) · Medicine & Science in Sports & Exercise · doi:10.1249/mss.0b013e3181659c4d · Cited by 174 · see citing works
Repeated doses administration of MDMA in humans: pharmacological effects and pharmacokinetics
Farré, M., de la Torre, R., Mathúna, B. Ó., Roset, P. N., Peiró, A. M., Torrens, M., Ortuño, J., Pujadas, M., & Camı́, J. (2004) · Psychopharmacology · doi:10.1007/s00213-004-1789-7 · Cited by 165 · see citing works
Increased intensity of Ecstasy and polydrug usage in the more experienced recreational Ecstasy/MDMA users: A WWW study
Scholey, A. B., Parrott, A. C., Buchanan, T., Heffernan, T., Ling, J., & Rodgers, J. (2004) · Addictive Behaviors · doi:10.1016/j.addbeh.2004.02.022 · Cited by 166 · see citing works
Use, abuse and dependence of ecstasy and related drugs in adolescents and young adults—a transient phenomenon? Results from a longitudinal community study
von Sydow, K., Lieb, R., Pfister, H., Höfler, M., & Wïttchen, H. (2002) · Drug and Alcohol Dependence · doi:10.1016/s0376-8716(01)00195-8 · Cited by 159 · see citing works
Mood, cognition and serotonin transporter availability in current and former ecstasy (MDMA) users: the longitudinal perspective
Thomasius, R., Zapletalova, P., Petersen, K. U., Buchert, R., Andresen, B., Wartberg, L., Nebeling, B., & Schmoldt, A. (2006) · Journal of Psychopharmacology · doi:10.1177/0269881106059486 · Cited by 158 · see citing works
MDMA (‘ecstasy’) use, and its association with high risk behaviors, mental health, and other factors among gay/bisexual men in New York City
Klitzman, R., Greenberg, J. D., Pollack, L. M., & Dolezal, C. L. (2002) · Drug and Alcohol Dependence · doi:10.1016/s0376-8716(01)00189-2 · Cited by 158 · see citing works
Interaction of Amphetamines and Related Compounds at the Vesicular Monoamine Transporter
Partilla, J. S., Dempsey, A. G., Nagpal, A., Blough, B. E., Baumann, M. H., & Rothman, R. B. (2006) · Journal of Pharmacology and Experimental Therapeutics · doi:10.1124/jpet.106.103622 · Cited by 153 · see citing works
Acute and long-term effects of MDMA on cerebral dopamine biochemistry and function
Colado, M. I., O’Shea, E., & Green, A. R. (2004) · Psychopharmacology · doi:10.1007/s00213-004-1788-8 · Cited by 153 · see citing works
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The health effects of ecstasy: a literature review
Gowing, L., HENRY‐EDWARDS, S. M., Irvine, R. J., & Ali, R. L. (2002) · Drug and Alcohol Review · doi:10.1080/09595230220119363 · Cited by 153 · see citing works
MDMA (3,4-Methylenedioxymethamphetamine) or Ecstasy: The Neuropsychobiological Implications of Taking It at Dances and Raves
Parrott, A. C. (2004) · Neuropsychobiology · doi:10.1159/000080961 · Cited by 152 · see citing works
The content of ecstasy tablets: implications for the study of their long‐term effects
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A review of acute effects of 3,4-methylenedioxymethamphetamine in healthy volunteers
Dumont, G. J. H., & Verkes, R. J. (2006) · Journal of Psychopharmacology · doi:10.1177/0269881106063271 · Cited by 149 · see citing works
Positron emission tomographic studies of brain dopamine and serotonin transporters in abstinent (±)3,4-methylenedioxymethamphetamine (“ecstasy”) users: relationship to cognitive performance
McCann, U. D., Szabó, Z. R., Vranešić, M., Palermo, M., Mathews, W. B., Ravert, H. T., Dannals, R. F., & Ricaurte, G. A. (2008) · Psychopharmacology · doi:10.1007/s00213-008-1218-4 · Cited by 149 · see citing works
Clinical Pharmacokinetics of Amfetamine and Related Substances
de la Torre, R., Farr, M., Navarro, M., Pacifici, R., Zuccaro, P., & Pichini, S. (2004) · Clinical Pharmacokinetics · doi:10.2165/00003088-200443030-00002 · Cited by 149 · see citing works
Uncoupling the agony from ecstasy
Mills, E., Banks, M. L., Sprague, J. E., & Finkel, T. (2003) · Nature · doi:10.1038/426403a · Cited by 148 · see citing works
Recreational drug use and human aggressive behavior: A comprehensive review since 2003
Tomlinson, M. F., Brown, M. F. D., & Hoaken, P. N. S. (2016) · Aggression and Violent Behavior · doi:10.1016/j.avb.2016.02.004 · Cited by 143 · see citing works
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3,4-Methylenedioxymethamphetamine (MDMA, “Ecstasy”)
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The acute and long-term effects of 3,4-\nmethylenedioxymethamphetamine (MDMA; ‘ecstasy’) upon\ncerebral and cerebrovascular serotonergic processes.
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The acute and long-term effects of 3,4-methylenedioxymethamphetamine (MDMA; 'ecstasy') upon cerebral and cerebrovascular serotonergic processes
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Authors: Green, A. R., Mechan, A. O., Elliott, J. M., O’Shea, E., & Colado, M. I.
Affiliations: AstraZeneca (United Kingdom) (GB)
ORCID: O’Shea, Esther
Venue: Pharmacological Reviews
Publisher: Elsevier BV
Published: 2003-09
Volume: 55
Issue: 3
Pages: 463-508
ISSN: 0031-6997 (ISSN-L)
DOI: 10.1124/pr.55.3.3
OpenAlex: W2132011757
Cited by: 1,272
References: 435
Citations by year: 2026: 18 · 2025: 19 · 2024: 25 · 2023: 19 · 2022: 30 · 2021: 18 · 2020: 71 · 2019: 24 · 2018: 28 · 2017: 30 · 2016: 50 · 2015: 43 · 2014: 64 · 2013: 68 · 2012: 72
FWCI: 16.58
Type: journal article
Language: en
Open access: closed
Licence: www.elsevier.com/tdm/userlicense/1.0/ (tdm)
www.elsevier.com/legal/tdmrep-license (tdm)
Locations: Pharmacological Reviews (publishedVersion)
PubMed (publishedVersion)
DMU Open Research Archive (De Montfort University) (submittedVersion)
Topics: Social Sciences › Psychology › Clinical Psychology › Psychedelics and Drug Studies
Life Sciences › Neuroscience › Cellular and Molecular Neuroscience › Neurotransmitter Receptor Influence on Behavior
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Forensic Toxicology and Drug Analysis
Keywords: MDMA, ecstasy, amphetamine derivatives, serotonin release, dopamine release, hyperthermia, serotonin neurotoxicity, free radicals, MDMA metabolites, recreational drug use, locomotor activity, long-term psychological effects, polydrug use
MeSH terms: Animals, Behavior, Animal, Body Temperature, Brain, Dopamine, Free Radicals, Hallucinogens, Humans, Hyperkinesis, Norepinephrine, Primates, Serotonin, Time Factors, N-Methyl-3,4-methylenedioxyamphetamine, Neurodegenerative Diseases, Mice, Rats

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The Pharmacology and Clinical Pharmacology of 3,4-Methylenedioxymethamphetamine (MDMA, “Ecstasy”)

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