MDMA
PubChem records this structure as 3,4-Methylenedioxymethamphetamine.
Also known as3,4-Methylenedioxymethamphetamine · Ecstasy · Midomafetamine · Methylenedioxymethamphetamine · midomafetamina · Methylenedioxymetamphetamine · Methylenedioxymethamfetamine · 3,4-methylenedioxymetamphetamine
1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
- PubChem CID
- 1615
- ChEMBL
- CHEMBL43048
- Measurements
- 37
- InChIKey
- SHXWCVYOXRDMCX-UHFFFAOYSA-N
I · Summary
What is known
Published passages, each quoted whole and attributed to the database that published it. Two blocks are written here rather than quoted, and both say so where they stand: the synthesized summary at the top, which may draw only on the passages beneath it, and the history note, which cites the works it came from. Every claim in either carries a marker to its source.
Synthesized summary
written by this site — every other word below is quoted
MDMA is a ring-substituted amphetamine — a benzodioxole carrying a 2-(methylamino)propyl group — which the sources relate structurally to mescaline while classing it among the amphetamines 1,2. Its described action is not one receptor but a sweep: an acute, rapid enhancement of serotonin release together with inhibition of serotonin reuptake, depletion of tryptophan hydroxylase through oxidative inactivation, release of norepinephrine, dopamine and acetylcholine, and direct action at α2-adrenergic and 5-HT2A receptors 2. Both the appeal and the alarm follow from that breadth. What the record gives for recreational use is a positive mood state — euphoria, intimacy and closeness to others — taken orally at dance events 4; the same records class it as a neurotoxin and describe marked, long-lasting changes in brain serotonergic systems 1,3. Clinical interest is stated as active but unfinished: trials in post-traumatic stress disorder and in anxiety associated with terminal cancer 5. One pharmacokinetic property is worth separating from the others because it is a mechanism for harm rather than a description of one — MDMA inhibits the CYP2D6 that clears it, so its kinetics are nonlinear, and a further dose can produce an unexpectedly high blood level that may worsen the drug's cardiovascular and other toxic effects 6,7. It is Schedule I 8.
Drawn only from the passages printed below, so every claim above can be checked against material on this page. The numbers are those passages. Synthesized by Claude Opus 5 (claude-opus-5), via Claude Code on 2026-08-27.
What it is
1cited by the summary above
3,4-methylenedioxymethamphetamine is a member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5. It has a role as a neurotoxin. It is a member of amphetamines and a member of benzodioxoles.
3,4-methylenedioxymethamphetamine is a DEA Schedule I controlled substance. Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse. It is a Hallucinogenic substances substance.
3cited by the summary above
An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems.
2cited by the summary above
3,4-Methylenedioxymethamphetamine is a ring-substituted amphetamine derivative, structurally related to the hallucinogen mescaline, with entactogenic, neurotoxic, and motor-stimulatory activities. 3,4-methylenedioxymethamphetamine (MDMA) produces an acute, rapid enhancement in both the release of serotonin from and the inhibition of serotonin reuptake by serotonergic nerve endings in the brain. Once within the cell, MDMA depletes stores of tryptophan hydroxylase (TPH) via acute oxidative inactivation; in turn, depleted stores of TPH leave cell terminals open to damage from oxidative stress, possibly a source of MDMA neurotoxicity. This agent also induces norepinephrine, dopamine, and acetylc…
Recognized use
Hallucinogens Serotonin Agents; Adrenergic Uptake Inhibitors
Therapeutic Uses
Hazardous Substances Data Bank (HSDB)National Library of Medicine's Medical Subject Headings. N-Methyl-3,4-methylenedioxyamphetamine. Online file (MeSH, 2017). Available from, as of October 6, 2017: https://www.nlm.nih.gov/mesh/2017/mesh_browser/MBrowser.html
/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations;…
Therapeutic Uses
Hazardous Substances Data Bank (HSDB)NIH/NLM; ClinicalTrials.Gov. Available from, as of October 6, 2017: https://clinicaltrials.gov/
/EXPL THER/ The first study of 3,4-methylenedioxymethamphetamine (MDMA)-assisted therapy for the treatment of social anxiety in autistic adults commenced in the spring of 2014. The search for psychotherapeutic options for autistic individuals is imperative considering the lack of effective conventional treatments for mental health diagnoses that are common in this population. Serious Adverse Events (SAEs) involving the administration of MDMA in clinical trials have been rare and non-life threatening. To date, MDMA has been administered to over 1133 individuals for research purposes without the occurrence of unexpected drug-related SAEs that require expedited reporting per FDA regulations. No…
Therapeutic Uses
Hazardous Substances Data Bank (HSDB)PMID 25818246Danforth AL et al; Prog Neuropsychopharmacol Biol Psychiatry 64: 237-49 (2016)
/EXPL THER/ l-3,4-dihydroxyphenylalanine (l-DOPA) is the most effective treatment for Parkinson's disease, but long-term l-DOPA administration is marred by the emergence of motor complications, namely, dyskinesia and a shortening of antiparkinsonian benefit (wearing-OFF). 3,4-methylenedioxymethamphetamine (MDMA) is unique in that it exerts antidyskinetic effects and may enhance antiparkinsonian actions of l-DOPA. MDMA is composed of two enantiomers with different pharmacological profiles; here, we describe a novel enantiospecific synthesis of the two enantiomers and expand on the previous characterization of their pharmacology. R-MDMA (rectus-MDMA) is relatively selective for 5-HT(2A) recept…
Therapeutic Uses
Hazardous Substances Data Bank (HSDB)PMID 21562283Huot P et al; J Neurosci 31 (19): 7190-8 (2011)
5cited by the summary above
Clinical trials are now testing the therapeutic potential of MDMA for post-traumatic stress disorder (PTSD) and anxiety associated with terminal cancer. MDMA is one of the four most widely used illicit drugs in the U.S.
Drug Indication
8cited by the summary above
3,4-Methylenedioxymethamphetamine (MDMA) (DEA Code Number: 7405) is a Schedule I controlled substance.
Use Classification
Hazardous Substances Data Bank (HSDB)21 CFR 1308.11(d) (USDEA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 19, 2017: https://www.ecfr.gov
Schedule I Controlled Substance: (A) The drug or other substance has a high potential for abuse; (B) The drug or other substance has no currently accepted medical use in treatment in the United States; and (C) There is a lack of accepted safety for use of the drug or other substance under medical supervision.
Use Classification
Hazardous Substances Data Bank (HSDB)US Department of Justice/Office of Diversion Control; Schedule of Controlled Substances. Available from, as of October 19, 2017: https://www.deadiversion.usdoj.gov/21cfr/21usc/812.htm
4cited by the summary above
Ecstasy is the popular name for the illicit drug MDMA and is widely used at dance parties or "raves." It is usually consumed orally in tablet or capsule form ... Its primary effect is to produce a positive mood state with euphoria, intimacy, and closeness to others.
Use Classification
Hazardous Substances Data Bank (HSDB)Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 346
For more Uses (Complete) data for 3,4-Methylenedioxymethamphetamine (6 total), please visit the HSDB record page.
Use Classification
How it acts
- Sodium-dependent dopamine transporter releasing agentRELEASING AGENTPMID 36311515
- Sodium-dependent serotonin transporter releasing agentRELEASING AGENTPMID 36311515
- Sodium-dependent noradrenaline transporter releasing agentRELEASING AGENTPMID 36311515
It enters neurons via carriage by the monoamine transporters. Once inside, MDMA inhibits the vesicular monoamine transporter, which results in increased concentrations of serotonin, norepinephrine, and dopamine into the cytoplasm, and induces their release by reversing their respective transporters through a process known as phosphorylation. It also acts as a weak 5-HT1 and 5-HT2 receptor agonist. MDMA's unusual entactogenic effects have been hypothesized to be, at least partly, the result of indirect oxytocin secretion via activation of the serotonin system. Oxytocin is a hormone released following events like hugging, orgasm, and childbirth, and is thought to facilitate bonding and the est…
3,4-Methylenedioxymethamphetamine (MDMA; "ecstasy") is a potentially neurotoxic recreational drug of abuse. Though the mechanisms involved are still not completely understood, formation of reactive metabolites and mitochondrial dysfunction contribute to MDMA-related neurotoxicity. Neuronal mitochondrial trafficking, and their targeting to synapses, is essential for proper neuronal function and survival, rendering neurons particularly vulnerable to mitochondrial dysfunction. Indeed, MDMA-associated disruption of Ca(2+) homeostasis and ATP depletion have been described in neurons, thus suggesting possible MDMA interference on mitochondrial dynamics. In this study, we performed real-time functi…
Hazardous Substances Data Bank (HSDB)PMID 24595818Barbosa DJ et al; Toxicol Sci 139 (2): 407-20 (2014)
Behavior carries the pharmacological classes and the acute-effect durations, with plasma half-life kept separate from duration of effect.
In the body
3,4-Methylenedioxymethamphetamine (MDMA), or ecstasy, is excreted as unchanged drug, 3,4-methylenedioxyamphetamine (MDA), and free and glucuronidated/sulfated 4-hydroxy-3-methoxymethamphetamine (HMMA), and 4-hydroxy-3-methoxyamphetamine (HMA) metabolites. The aim of this paper is to describe the pattern and timeframe of excretion of MDMA and its metabolites in urine. Placebo, 1.0 mg/kg, and 1.6 mg/kg oral MDMA doses were administered double-blind to healthy adult MDMA users on a monitored research unit. All urine was collected, aliquots were hydrolyzed, and analytes quantified by gas chromatography-mass spectrometry. Median C(max), T(max), ratios, first and last detection times, and detectio…
Absorption, Distribution and Excretion
Hazardous Substances Data Bank (HSDB)PMID 19874650Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3159864
Based on animal data, there is speculation that (+ or -)-3,4-methylenedioxymethamphetamine (MDMA) is neurotoxic to humans. Extrapolation of MDMA findings from animals to humans requires assessment of pharmacokinetics in various species, and low-dose administration data from rats are lacking. In this study, we examine MDMA pharmacokinetics in rats given low (2 mg/kg) and high (10 mg/kg) doses of racemic MDMA via intraperitoneal, subcutaneous, and oral routes. Repeated blood specimens were collected from venous catheters, and plasma was assayed for MDMA and its metabolites, 4-hydroxy-3-methoxymethamphetamine (HMMA) and 3,4-methylenedioxyamphetamine (MDA), by gas chromatography-mass spectrometr…
Absorption, Distribution and Excretion
Hazardous Substances Data Bank (HSDB)PMID 19679675Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774984
3,4-Methylenedioxymethamphetamine (MDMA) is a widely abused illicit drug that can cause severe and even fatal adverse effects. However, interest remains for its possible clinical applications in posttraumatic stress disorder and anxiety treatment. Preclinical studies to determine MDMA's safety are needed. We evaluated MDMA's pharmacokinetics and metabolism in male rats receiving 2.5, 5, and 10 mg/kg s.c. MDMA, and the associated pharmacodynamic consequences. Blood was collected via jugular catheter at 0, 0.5, 1, 2, 4, 6, 8, 16, and 24 hours, with simultaneous serotonin (5-HT) behavioral syndrome and core temperature monitoring. Plasma specimens were analyzed for MDMA and the metabolites (+/-…
Absorption, Distribution and Excretion
Hazardous Substances Data Bank (HSDB)PMID 24141857Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3876787
7cited by the summary above
MDMA is rapidly absorbed into the human bloodstream, but once in the body, MDMA metabolites interfere with the body's ability to metabolize, or break down, the drug. As a result, additional doses of MDMA can produce unexpectedly high blood levels, which could worsen the cardiovascular and other toxic effects of this drug.
Absorption, Distribution and Excretion
Hazardous Substances Data Bank (HSDB)DHHS/NIH; NIDA Research Report Series on MDMA (Ecstasy) Abuse p.14 (2006). Available from, as of October 6, 2017: https://www.nida.nih.gov/PDF/RRmdma.pdf
6cited by the summary above
Midomafetamine, or MDMA, is reported to undergo extensive CYP-mediated hepatic metabolism, with CYP2D6 playing a major role in humans. Other CYP enzymes contributing to MDMA metabolism are CYP3A4 and COMT. MDMA is metabolized via two primary metabolic pathways. It may undergo O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation. In contrast, it may also undergo N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine. Due to autoinhibition of CYP2D6 and CYP2D8, MDMA displays a complex, nonlinear pharmacokinetics profile, with the zeroth order kinetics occurring a…
Metabolism/Metabolites
MDMA (3,4-methylenedioxymethamphetamine) metabolism is a major cause of MDMA-mediated hepatotoxicity. In this study the effects of MDMA and its metabolites on the glutathione system were evaluated. Glutathione (GSH/GSSG) levels and gene expression of glutamate cysteine ligase catalytic subunit (GCLC), glutathione-S-transferase (GST) and pregnane X receptor (PXR) were compared in the immortalized human liver epithelial cell line THLE-Neo lacking phase I metabolism and primary rat hepatocytes expressing both phase I and II metabolism. Furthermore, we evaluated the potential protective effects of two antioxidants, N-acetyl-cysteine (NAC) and sulforaphane (SFN) in these cell systems. In THLE-Neo…
Metabolism/Metabolites
Hazardous Substances Data Bank (HSDB)PMID 21871945Antolino-Lobo I et al; Toxicology 289 (2-3): 175-84 (2011)
3,4-Methylenedioxymethamphetamine (MDMA; ecstasy) is a ring-substituted amphetamine widely used for recreational purposes. MDMA is predominantly O-demethylenated in humans by cytochrome P450 (CYP) 2D6, and is also a potent mechanism-based inhibitor of the enzyme. After assessing the inhibition and recovery of CYP2D6 in a previous study, the aim of this work was to study in humans the activity of CYP1A2 in vivo after CYP2D6 had been inhibited by MDMA, using caffeine as a probe drug. Twelve male and nine female recreational MDMA users were included. In session 1, 100 mg of caffeine was given at 0 hr. In session 2, a 1.5 mg/kg MDMA dose (range 75-100 mg) was given at 0 hr followed by a 100 mg d…
Metabolism/Metabolites
Hazardous Substances Data Bank (HSDB)PMID 22673010Yubero-Lahoz S et al; Drug Metab Pharmacokinet 27 (6): 605-13 (2012)
The R- and S-enantiomers of racemic 3,4-methylenedioxymethamphetamine (MDMA) exhibit different dose-concentration curves. In plasma, S-MDMA was eliminated at a higher rate, most likely due to stereoselective metabolism. Similar data were shown in various in vitro experiments. The aim of the present study was the in vivo investigation of stereoselective elimination of MDMA's phase I and phase II metabolites in human urine following controlled oral MDMA administration. Urine samples from 10 participants receiving 1.0 and 1.6 mg/kg MDMA separated by at least one week were analyzed blind by liquid chromatography-high resolution-mass spectrometry and gas chromatography-mass spectrometry after chi…
Metabolism/Metabolites
Hazardous Substances Data Bank (HSDB)PMID 21983032Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3225738
History, discovery and cultural use
Written by this site · every claim referenced
MDMA was synthesized and patented by chemists at Merck in 1912 1. U.S. Army Intelligence pursued it in the 1950s, work that ended when a participant died; interest resurged in the mid-1970s, and by the early 1980s it had become widely used as a club drug 1. The first Phase 1 safety study was conducted by Grob and colleagues in the early 1990s 1.
Every claim is from ref 1, read directly at NBK587225. Nothing above is quoted from MDMA’s own database records; those appear as quotations elsewhere on this plate.
Histories of this field
Scholarship on psychedelics generally, not on MDMA specifically. Whether any of these treats this compound is a question for the book, not for this page.
Mescaline: A Global History of the First Psychedelic
Traces mescaline and the peyote and San Pedro cacti from pre-Columbian ritual use through nineteenth-century chemistry to twentieth-century psychiatry and the counterculture.
Jay M. Mescaline: A Global History of the First Psychedelic. Yale University Press, New Haven and London; 2019. ISBN 9780300231076.
Expanding Mindscapes: A Global History of Psychedelicsopen access
Essays on the international and cross-cultural history of psychedelic science, deliberately decentring the standard North American and European account.
Dyck E, Elcock C, editors. Expanding Mindscapes: A Global History of Psychedelics. The MIT Press, Cambridge MA; 2023. ISBN 9780262546935 (paper), 9780262376891 (open access). doi:10.7551/mitpress/14417.001.0001.
Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers
Botany, ethnography and chemistry of the principal hallucinogenic plants, by the founder of modern ethnobotany and the chemist who first synthesized LSD.
Schultes RE, Hofmann A, Rätsch C. Plants of the Gods: Their Sacred, Healing, and Hallucinogenic Powers. 2nd ed. Healing Arts Press, Rochester VT; 2001. ISBN 9780892819799.
Psychonauts: Drugs and the Making of the Modern Mind
The tradition of scientific self-experimentation with psychoactive drugs, and its part in the emergence of psychology and of modernism.
Jay M. Psychonauts: Drugs and the Making of the Modern Mind. Yale University Press, New Haven; 2023. ISBN 9780300257946.
Ancient Psychoactive Substances
Archaeological and bioarchaeological evidence for psychoactive plant use across the ancient world.
Fitzpatrick SM, editor. Ancient Psychoactive Substances. University Press of Florida, Gainesville; 2018. ISBN 9780813056708.
A chapter tracing psychedelic and entactogen research from earlier ritual use through the mid-century research period to current clinical trials.
Stroud C, Posey Norris SM, Matney C, editors. History and Current Status of Psychedelics and Entactogens for the Treatment of Psychiatric Disorders. In: Exploring Psychedelics and Entactogens as Treatments for Psychiatric Disorders: Proceedings of a Workshop. National Academies Press, Washington DC; 2022. NBK587225.
Workshop proceedings record what participants said; they are not a consensus statement of the National Academies.
Peer-reviewed review covering the isolation, synthesis, pharmacology and ritual use of peyote and mescaline.
Dinis-Oliveira RJ, Pereira CL, da Silva DD. Pharmacokinetic and Pharmacodynamic Aspects of Peyote and Mescaline: Clinical and Forensic Repercussions. Current Molecular Pharmacology 12(3):184–194; 2019. doi:10.2174/1874467211666181010154139.
Institutional archives
- Heffter Research Institute Funds and coordinates clinical research on psilocybin, and keeps records of the studies it has supported since 1993. Sponsors the research it archives.
- Multidisciplinary Association for Psychedelic Studies (MAPS) Sponsors clinical research, chiefly on MDMA-assisted therapy, and publishes an archive of historical and contemporary documents. A sponsor and an advocacy organization, not a disinterested archive; its clinical programme has a commercial arm.
The rest of this dossier
- Affinity — 37 measurements in this archive, equilibrium constants kept apart from functional readouts.
- Toxicology — 9 published passages, plus any assay in this archive bearing on toxicity.
- Legal — DEA Schedule I, with the passage it was read from.
- Systems — where this compound’s targets are transcribed, by brain region and tissue.
Passages via PubChem descriptive sections, aggregating DrugBank, LiverTox, FDA, DEA, HSDB, EPA. Each is quoted whole and attributed to the database that published it. The only prose written here about MDMA is the history note, which says so on its face and carries a reference for every claim in it.
II · Identity
Structure and descriptors
Descriptors are computed here with RDKit from the structure PubChem returns — not from the archive's stored copy, so an edited local structure cannot reach this table.
- Formula
- C11H15NO2R
- Molecular weight
- 193.25g/molR
- Exact mass
- 193.1103DaR
- cLogP
- 1.57R
- TPSA
- 30.5ŲR
- H-bond donors
- 1R
- H-bond acceptors
- 3R
- Rotatable bonds
- 3R
- Aromatic rings
- 1R
- Heavy atoms
- 14R
- Fraction sp³
- 0.455R
- Formal charge
- 0R
Computed with RDKit 2025.09.2 from the SMILES returned by PubChem. Audit run 26/09/2026.
Bemis–Murcko scaffold
c1ccc2c(c1)OCO2
Shared with 1,3-Benzodioxolyl-N-ethylbutanamine, 1,3-Benzodioxolyl-N-ethylpentanamine, 1,3-Benzodioxolyl-N-methylpentanamine, 1,3-Benzodioxolylbutanamine, 2-Bromo-4,5-methylenedioxyamphetamine, 2,3-Dimethoxy-4,5-methylenedioxyamphetamine and 31 more. All families
III · Behavior
Behavioral summary
Class, mechanism, and the duration of acute effects — each quoted from the record or trial that publishes it. Duration of effects and plasma half-life are shown separately, because they are different quantities and diverge by a factor of three or four.
Classification
Duration of acute subjective effects
4.1 ± 0.4 h
125 mg, oral
“MDA produced stronger and longer-lasting subjective "any drug effects" compared with MDMA, with effect durations of (mean ± SEM) 6.1 ± 0.5 vs 4.1 ± 0.4 h, respectively”
4.8 h
“The average subjective effect duration of 30 mg 2C-B was 4.9 h and similar to MDMA (4.8 h) and shorter than psilocybin (6.1 h)”
Plasma elimination half-life
How fast the body clears the drug — not how long the effects last. The two diverge sharply: LSD is cleared with a half-life of about 2.6 h while its subjective effects run 8–12 h.
The present study compared the disposition and metabolism of the recreational drug (+/-) 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") in squirrel monkeys and humans because the squirrel monkey has been extensively studied for MDMA neurotoxicity. ... The elimination half-life of MDMA was considerably shorter in squirrel monkeys than…
Hazardous Substances Data Bank (HSDB)PMID 19417716Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3159867 ... In this study, we examine MDMA pharmacokinetics in rats given low (2 mg/kg) and high (10 mg/kg) doses of racemic MDMA via intraperitoneal, subcutaneous, and oral routes. Repeated blood specimens were collected from venous catheters, and plasma was assayed for MDMA and its metabolites, 4-hydroxy-3-methoxymethamphetamine (HMMA) and 3,4-…
Hazardous Substances Data Bank (HSDB)PMID 19679675Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2774984 ... Elimination half-life was 8.6 hr /(75 mg)/ and 7.7 hr /(125 mg)/ for low and high dose 3,4-methylenedioxymethamphetamine /in eight men with experience in the recreational use of 3,4-methylenedioxymethamphetamine/ ...
Hazardous Substances Data Bank (HSDB)PMID 10381769Mas M et al; J Pharmacol Exp Ther 290 (1): 136-45 (1999) 6–10 (though duration of effects is typically actually 3–5 hours)
DrugBank
Primary pharmacological drivers
Mechanism, as published
Quoted verbatim from the database named after each passage, never summarized.
3,4-Methylenedioxymethamphetamine (MDMA; "ecstasy") is a potentially neurotoxic recreational drug of abuse. Though the mechanisms involved are still not completely understood, formation of reactive metabolites and mitochondrial dysfunction contribute to MDMA-related neurotoxicity. Neuronal mitochondrial trafficking, and their targeting to…
Hazardous Substances Data Bank (HSDB)PMID 24595818Barbosa DJ et al; Toxicol Sci 139 (2): 407-20 (2014) The aim of the present study was to identify the neural substrate underlying memory impairment due to a single dose of MDMA (3,4-methylenedioxymethamphetamine) by means of pharmaco-MRI. Based on previous behavioral results it was hypothesized that this deficit could be attributed to a specific influence of MDMA on encoding. Fourteen Ecsta…
Hazardous Substances Data Bank (HSDB)PMID 21616977Kuypers KP et al; J Psychopharmacol 25 (8): 1053-61 (2011) The recreational drug 3,4-methylenedioxymethamphetamine (MDMA; 'ecstasy') produces a neuro-inflammatory response in rats characterized by an increase in microglial activation and IL-1beta levels. The integrity of the blood-brain barrier (BBB) is important in preserving the homeostasis of the brain and has been shown to be affected by neur…
Hazardous Substances Data Bank (HSDB)PMID 24626059Rubio-Araiz A et al; Int J Neuropsychopharmacol 17 (8): 1243-55 (2014) It enters neurons via carriage by the monoamine transporters. Once inside, MDMA inhibits the vesicular monoamine transporter, which results in increased concentrations of serotonin, norepinephrine, and dopamine into the cytoplasm, and induces their release by reversing their respective transporters through a process known as phosphorylati…
DrugBank MDMA acts as a releasing agent of serotonin, norepinephrine, and dopamine.
DrugBank
IV · Clinical
Clinical description
Where this compound's substance class sits in ICD-11 and DSM-5-TR, and how much of the recorded literature speaks to each domain of a mental status examination.
Filed under Hallucinogens
- 6C49Disorders due to use of hallucinogens
Diagnostic and Statistical Manual of Mental Disorders, Fifth Edition, Text Revision (DSM-5-TR): Hallucinogen-Related Disorders. Category names only — the manual is in copyright and no diagnostic criterion is reproduced here.
How much has been written about each domain
The clinical domains, and how many of the records this archive holds for this compound say something under each. What the terms mean, and the word list behind every spoke, are set out in the method.
- Cognition 4
- matched on “cognitiv”, “concentrat”, “memory” · in Pharmacology: Mechanism of Action; PMID 21616977; PMID 10811690; PMID 26073279
V · Systems
Systems physiology
Where the targets this compound binds are transcribed — brain regions on the left, peripheral and autonomic tissues on the right. A join of two measurements, not a claim about what the compound does to either.
Brain
basal ganglia: drawn as the caudate nucleus, putamen and globus pallidus.
Measured but not drawn — this anatomogram has no outline for them: midbrain 92.9, retina 7.8, pituitary gland 4.7, spinal cord 1.4.
Body
Square-root ramp · shared scale across both plates
Shading is transcript level — not affinity, and not affinity combined with expression. Outlined but unshaded organs hold none of this compound’s resolved targets above the atlas’s detection threshold. Anatomy from EMBL-EBI Anatomogram (Apache License 2.0); regions identified by Uberon (uberon.org), CC BY 3.0.
Brain regions
Regions where this compound's measured targets are transcribed. Linked from the plate above.
midbrain
92.9 nTPMbasal ganglia
26.0 nTPMcerebral cortex
18.2 nTPMretina
7.8 nTPMamygdala
6.4 nTPMcerebellum
5.8 nTPMhypothalamus
5.3 nTPMpituitary gland
4.7 nTPMhippocampal formation
4.6 nTPMspinal cord
1.4 nTPM
Peripheral & autonomic
Tissues outside the CNS expressing the same targets — where a compound's bodily effects become possible.
liver
56.2 nTPMsmall intestine
38.0 nTPMkidney
33.4 nTPMpancreas
28.8 nTPMlung
27.2 nTPMspleen
20.8 nTPMadrenal gland
17.2 nTPMsmooth muscle
15.7 nTPMurinary bladder
14.8 nTPMduodenum
9.7 nTPMheart muscle
9.4 nTPMthyroid gland
8.7 nTPMcolon
8.5 nTPMsalivary gland
6.5 nTPMskeletal muscle
6.0 nTPMstomach 1
4.4 nTPM
Each row joins two published measurements and nothing else: the affinity this archive holds for the compound at that target, and the transcript level the Human Protein Atlas reports for that target’s gene in that region. Bars scale with expression only. Expression is not activation — a receptor transcribed in a region is a receptor available to be bound there, which is a weaker and more defensible claim than saying the region is affected.
Expression data from Human Protein Atlas (CC BY-SA 3.0), RNA expression, nTPM (normalized transcripts per million), consensus tissue dataset. Uhlén M, et al. Tissue-based map of the human proteome. Science. 2015;347(6220):1260419.
VI · Profile
Affinity rosette
The strongest measurement at each of 10 molecular targets. Cell-line and whole-organism screens are excluded here — they carry no affinity — and appear in the table below.
VII · Toxicology
Toxicological profile
What has been measured, and what has been published — kept apart, and neither scored. There is no risk rating on this page; the archive once carried one, identical for every compound, produced by a stub.
Measured in this archive
Assays that bear on toxicity, drawn from the same ChEMBL records as everything else on this page. They are measurements of what a compound binds or does to cells — not verdicts about what it does to a person.
No hERG, cytochrome, cytotoxicity or transport measurement exists for MDMA in this archive.
Lethal-dose values — animal studies
These are not human doses. An LD50 is the dose killing half of a group of animals of one species by one route, and it is a poor predictor of human risk for these compounds. Each value is printed whole, with the species and route it was measured in, because a lethal dose separated from those two facts is worse than no figure at all. Nothing here supports inferring a safe dose for anyone.
LD50 Mouse ip 97 mg/kg /MDMA hydrochloride/
Hazardous Substances Data Bank (HSDB)O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1071
LD50 Rat ip 49 mg/kg /MDMA hydrochloride/
Hazardous Substances Data Bank (HSDB)O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1071
LD50 Guinea pig ip 98 mg/kg /MDMA hydrochloride/
Hazardous Substances Data Bank (HSDB)O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1071
As published
Quoted verbatim from the database named after each passage, never summarized — a summary of a toxicology statement is a new claim.
Toxicity Summary
IDENTIFICATION AND USE: 3,4-Methylenedioxymethamphetamine (MDMA) is a schedule I controlled substance. Ecstasy is the popular name for the illicit drug MDMA and is widely used at dance parties. It is usually consumed orally in tablet or capsule form. MDMA acts as both a stimulant and psychedelic, producing an energizing effect, as well as distortions in time and perception and enhanced enjoyment from tactile experien…
Human Toxicity Excerpts
/HUMAN EXPOSURE STUDIES/ A comprehensive cognitive test battery was administered to 28 abstinent ecstasy users with concomitant use of cannabis only and to two equally sized matched groups of cannabis users and non-users. The sample consisted of ecstasy users with a typical recreational use pattern and did not include very heavy users. Ecstasy users were unimpaired in simple tests of attention (alertness). However, t…
Hazardous Substances Data Bank (HSDB)PMID 10811690Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1736965
/HUMAN EXPOSURE STUDIES/ 3,4-Methylenedioxymethamphetamine (MDMA, ecstasy) is a popular psychostimulant, frequently associated with multiple administrations over a short period of time. Repeated administration of MDMA in experimental settings induces tolerance and metabolic inhibition. The aim is to determine the acute pharmacological effects and pharmacokinetics resulting from two consecutive 100 mg doses of MDMA se…
Hazardous Substances Data Bank (HSDB)PMID 26073279Farre M et al; Eur Neuropsychopharmacol 25 (10): 1637-49 (2015)
/HUMAN EXPOSURE STUDIES/ The synthetic psychostimulant MDMA (+/- 3,4-methylenedioxymethamphetamine, ecstasy) acts as an indirect serotonin, dopamine, and norepinephrine agonist and as a mechanism-based inhibitor of the cytochrome P-450 2D6 (CYP2D6). It has been suggested that women are more sensitive to MDMA effects than men but no clinical experimental studies have satisfactorily evaluated the factors contributing t…
Hazardous Substances Data Bank (HSDB)PMID 23112822Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3480420
/HUMAN EXPOSURE STUDIES/ 3-4-Methylenedioxymethamphetamine (MDMA) increases self-reported positive social feelings and decreases the ability to detect social threat in faces, but its effects on experiences of social acceptance and rejection have not been determined. We examined how an acute dose of MDMA affects subjective and autonomic responses to simulated social acceptance and rejection. We predicted that MDMA wou…
Hazardous Substances Data Bank (HSDB)PMID 24316346Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3910346
For more Human Toxicity Excerpts (Complete) data for 3,4-Methylenedioxymethamphetamine (64 total), please visit the HSDB record page.
Published passages via PubChem toxicology sections, aggregating Hazardous Substances Data Bank (HSDB), RTECS, LiverTox. No figure on this page is scored, ranked or combined into a risk level.
VIII · Evidence
Every measurement
One row per published value. The identifier in the last column resolves to the ChEMBL assay record it was read from.
Equilibrium binding constants 31
Ki and Kd — a concentration at equilibrium. Directly comparable across rows at the same target.
| Target | Class | Type | Value (nM) | pX | Organism | Assay |
|---|---|---|---|---|---|---|
| SERT | Monoamine transporters | Ki | 0.730 | 9.14 | HUMAN | PMID 18487050 |
| SERT | Monoamine transporters | Ki | 2.03 | 8.69 | HUMAN | PMID 18487050 |
| SERT | Monoamine transporters | Ki | 72.00 | 7.14 | RAT | PMID 12761331 |
| NET | Monoamine transporters | Ki | 110 | 6.96 | RAT | PMID 12761331 |
| SERT | Monoamine transporters | Ki | 238 | 6.62 | RAT | PMID 11071707 |
| DAT | Monoamine transporters | Ki | 278 | 6.56 | RAT | PMID 12761331 |
| D1 | Dopamine receptors | Ki | 370 | 6.43 | RAT | PMID 22897747 |
| NET | Monoamine transporters | Ki | 462 | 6.34 | RAT | PMID 11071707 |
| 5-HT2B | Serotonin receptors | Ki | 500 | 6.30 | HUMAN | PMID 12761331 |
| 5-HT2B | Serotonin receptors | Ki | 700 | 6.15 | HUMAN | PDSP |
| Alpha2C | Adrenergic receptors | Ki | 1,123 | 5.95 | HUMAN | PMID 12761331 |
| Alpha2C | Adrenergic receptors | Ki | 1,123 | 5.95 | HUMAN | PDSP |
| DAT | Monoamine transporters | Ki | 1,572 | 5.80 | RAT | PMID 11071707 |
| Alpha2B | Adrenergic receptors | Ki | 1,785 | 5.75 | HUMAN | PMID 12761331 |
| Alpha2B | Adrenergic receptors | Ki | 1,785 | 5.75 | HUMAN | PDSP |
| M3 | Unclassified | Ki | 1,851 | 5.73 | HUMAN | PMID 12761331 |
| M3 | Unclassified | Ki | 1,851 | 5.73 | HUMAN | PDSP |
| 5-HT2B | Serotonin receptors | Ki | 2,000 | 5.70 | HUMAN | PMID 12761331 |
| H1 | Unclassified | Ki | 2,138 | 5.67 | HUMAN | PDSP |
| H1 | Unclassified | Ki | 2,138 | 5.67 | HUMAN | PMID 12761331 |
| D1 | Dopamine receptors | Ki | 2,400 | 5.62 | MOUSE | PMID 22897747 |
| Alpha2A | Adrenergic receptors | Ki | 2,532 | 5.60 | HUMAN | PMID 12761331 |
| Alpha2A | Adrenergic receptors | Ki | 2,532 | 5.60 | HUMAN | PDSP |
| Alpha1A | Adrenergic receptors | Ki | 6,000 | 5.22 | HUMAN | PMID 22897747 |
| M5 | Unclassified | Ki | 6,339 | 5.20 | HUMAN | PMID 12761331 |
| M5 | Unclassified | Ki | 6,339 | 5.20 | HUMAN | PDSP |
| DAT | Monoamine transporters | Ki | 6,500 | 5.19 | HUMAN | PMID 22897747 |
| 5-HT2A | Serotonin receptors | Ki | 7,800 | 5.11 | HUMAN | PMID 22897747 |
| M4 | Unclassified | Ki | 8,245 | 5.08 | HUMAN | PMID 12761331 |
| M4 | Unclassified | Ki | 8,245 | 5.08 | HUMAN | PDSP |
| 5-HT2A | Serotonin receptors | Ki | 8,300 | 5.08 | RAT | PDSP |
Functional readouts 6
IC₅₀, EC₅₀, AC₅₀ and potency. Assay-dependent, and not interchangeable with a binding constant.
| Target | Class | Type | Value (nM) | pX | Organism | Assay |
|---|---|---|---|---|---|---|
| NET | Monoamine transporters | IC50 | 405 | 6.39 | Homo sapiens | CHEMBL1116588 |
| NET | Monoamine transporters | IC50 | 405 | 6.39 | Homo sapiens | CHEMBL1169103 |
| SERT | Monoamine transporters | IC50 | 425 | 6.37 | Homo sapiens | CHEMBL1116587 |
| SERT | Monoamine transporters | IC50 | 425 | 6.37 | Homo sapiens | CHEMBL1169102 |
| DAT | Monoamine transporters | IC50 | 1,442 | 5.84 | Homo sapiens | CHEMBL1116589 |
| DAT | Monoamine transporters | IC50 | 1,442 | 5.84 | Homo sapiens | CHEMBL1169104 |
- P
- PubChem
- C
- ChEMBL
- R
- Computed here with RDKit
- D
- Derived here from the stored measurement
IX · Trials
Registered clinical trials
Studies filed with ClinicalTrials.gov that name this compound as an intervention. A registered trial is a protocol, not a result — status and enrollment are printed beside every row, and withdrawn studies are counted rather than hidden.
107T
Registered studies
33T
Open or ongoing
104T
With a phase recorded
By phase
A study may carry two phase codes at once, so these count studies bearing each phase and do not sum to the total.
- Early phase 110
- Phase 136
- Phase 245
- Phase 38
- Not applicable9
By status
The registry’s own status for each record. Withdrawn and terminated studies are counted here rather than hidden — a stopped trial is part of what is known.
- Completed60
- Recruiting23
- Withdrawn6
- Not yet recruiting4
- Terminated4
- Active, not recruiting3
- Enrolling by invitation3
- Unknown status3
- No longer available1
The 25 most recently started, of 107
Newest first by start date. Each identifier opens the registry record it came from; the title is the sponsor’s own, quoted.
- NCT07765693Not yet recruiting · Phase 2
MDMA-AT for PTSD in Young Adults With Childhood Trauma
- Enrollment
- 15Testimated
- Started
- 2026-10-31
- Sponsor
- Jenna M. Traynor
Conditions Posttraumatic Stress Disorder (PTSD)
Matched “MDMA” in the study’s intervention “MDMA assisted psychotherapy”
- NCT05455996Not yet recruiting · Phase 2
MDMA-Assisted Therapy for Stress Disorders in Healthcare Workers and First Responders
- Enrollment
- 30Testimated
- Started
- 2026-10
- Sponsor
- Nautilus Sanctuary
Conditions Post-Traumatic Stress Disorder · Adjustment Disorders
Matched “MDMA” in the study’s intervention “MDMA”
- NCT06066853Recruiting · Early phase 1
MDMA-assisted Therapy for Fibromyalgia
- Enrollment
- 20Testimated
- Started
- 2026-09-15
- Sponsor
- Spaulding Rehabilitation Hospital
Conditions Fibromyalgia
Matched “MDMA” in the study’s intervention “MDMA”
- NCT07288151Recruiting · Phase 2
MDMA-Assisted Massed Exposure Therapy for PTSD
- Enrollment
- 200Testimated
- Started
- 2026-07
- Sponsor
- Emory University
Conditions Post Traumatic Stress Disorder
Matched “3,4-Methylenedioxymethamphetamine” in the study’s intervention “3,4-Methylenedioxymethamphetamine (MDMA)”
- NCT07569159Recruiting · Phase 2
MDMA Therapy in Veterans With PTSD
- Enrollment
- 52Testimated
- Started
- 2026-06-30
- Sponsor
- Sunstone Medical
Conditions Post Traumatic Stress Disorder
Matched “MDMA” in the study’s intervention “MDMA”
- NCT07555132Not yet recruiting · Not applicable
Circulating Oxytocin Changes in Response to MDMA vs. Placebo in Adult Patients With Autism Spectrum Disorder and Matched Healthy Controls
- Enrollment
- 40Testimated
- Started
- 2026-06
- Sponsor
- University Hospital, Basel, Switzerland
Conditions Autism Spectrum Disorder
Matched “MDMA” in the study’s intervention “MDMA”
- NCT07542145Recruiting · Phase 1
MDMA Assisted Therapy for BN
- Enrollment
- 40Testimated
- Started
- 2026-05-22
- Sponsor
- Icahn School of Medicine at Mount Sinai
Conditions Bulimia Nervosa
Matched “MDMA” in the study’s intervention “MDMA-AT”
- NCT07118839Recruiting · Phase 2 / Phase 3
MDMA-Assisted Therapy for Veterans With PTSD and Alcohol Use Disorder
- Enrollment
- 80Testimated
- Started
- 2026-05-18
- Sponsor
- VA Office of Research and Development
Conditions Post Traumatic Stress Disorder · Alcohol Use Disorder
Matched “MDMA” in the study’s intervention “Full Dose MDMA”
- NCT07584720Active, not recruiting · Phase 1
Study of Midomafetamine in Healthy Adults
- Enrollment
- 32Testimated
- Started
- 2026-04-23
- Sponsor
- Resilient Pharmaceuticals
Conditions Healthy Volunteers
Matched “Midomafetamine” in the study’s intervention “Midomafetamine HCl”
- NCT03606538Not yet recruiting · Phase 1
MDMA in Subjects With Moderate Hepatic Impairment and Subjects With Normal Hepatic Function
- Enrollment
- 16Testimated
- Started
- 2026-03-29
- Sponsor
- Resilient Pharmaceuticals
Conditions Pharmacokinetics · Hepatic Impairment
Matched “Midomafetamine” in the study’s intervention “Midomafetamine HCl”
- NCT07494214Recruiting · Phase 1
Acute Analgesic Effects of MDMA on Experimentally Induced Acute Pain, Hyperalgesia and Allodynia in Healthy Participants
- Enrollment
- 20Testimated
- Started
- 2026-03-09
- Sponsor
- University Hospital, Basel, Switzerland
Conditions Healhty
Matched “MDMA” in the study’s intervention “MDMA 25 mg”
- NCT07102576Recruiting · Phase 1
MDMA-Assisted Therapy for Mental Healthcare Providers
- Enrollment
- 30Testimated
- Started
- 2026-02-11
- Sponsor
- Rachel Yehuda
Conditions Mental Wellbeing
Matched “MDMA” in the study’s intervention “MDMA Hydrochloride”
- NCT04454684Withdrawn · Phase 2
A Multi-Site Study of MDMA-Assisted Psychotherapy for Eating Disorders
- Enrollment
- 0Tactual
- Started
- 2026-02
- Sponsor
- Resilient Pharmaceuticals
Conditions Anorexia Nervosa Restricting Type · Binge-Eating Disorder
Matched “Midomafetamine” in the study’s intervention “Midomafetamine”
- NCT07301632Recruiting · Phase 2
Ecstasy to Alleviate SEvere Chronic Neuropathic Pain Trial
- Enrollment
- 50Testimated
- Started
- 2026-01-30
- Sponsor
- Unity Health Toronto
Conditions Chronic Neuropathic Pain
Matched “3,4-Methylenedioxymethamphetamine” in the study’s intervention “3,4-Methylenedioxymethamphetamine”
- NCT07469098Recruiting · Phase 2
Group vs Individual MDMA-Assisted Therapy for PTSD After the October 7, 2023 Events
- Enrollment
- 168Testimated
- Started
- 2025-12-24
- Sponsor
- Sheba Medical Center
Conditions PTSD
Matched “MDMA” in the study’s intervention “MDMA HCl”
- NCT07303907Recruiting · Phase 2
A Phase 2A Trial of DT402 for Autism Spectrum Disorder
- Enrollment
- 20Testimated
- Started
- 2025-12-03
- Sponsor
- Definium Therapeutics US, Inc.
Conditions Autism Spectrum Disorder · ASD
Matched “3,4-Methylenedioxymethamphetamine” in the study’s intervention “DT402 (R-enantiomer of 3,4-methylenedioxymethamphetamine (MDMA))”
- NCT06989957Recruiting · Phase 1
Psilocybin and Methylenedioxymethamphetamine (MDMA) for Post-traumatic Stress Disorder (PTSD)
- Enrollment
- 40Testimated
- Started
- 2025-09-17
- Sponsor
- Johns Hopkins University
Conditions Posttraumatic Stress Disorder
Matched “MDMA” in the study’s intervention “MDMA”
- NCT06683014Recruiting · Phase 2
MDMA in Borderline Personality Disorder
- Enrollment
- 10Testimated
- Started
- 2025-09-05
- Sponsor
- Yale University
Conditions Borderline Personality Disorder
Matched “MDMA” in the study’s intervention “MDMA”
- NCT06905652Completed · Phase 1
Comparative Acute Effects of R-MDMA and S-MDMA in Healthy Participants
- Enrollment
- 26Tactual
- Started
- 2025-07-29
- Sponsor
- University Hospital, Basel, Switzerland
Conditions Healthy
Matched “3,4-Methylenedioxymethamphetamine” in the study’s intervention “R-3,4-methylenedioxymethamphetamine”
- NCT06353282Withdrawn · Phase 2
MDMA-Assisted Psychotherapy for Treatment Resistant PTSD in Adolescents
- Enrollment
- 0Tactual
- Started
- 2025-07-01
- Sponsor
- University of California, Los Angeles
Conditions PTSD, Post Traumatic Stress Disorder · Adolescents · Psychotherapy
Matched “MDMA” in the study’s intervention “MDMA”
- NCT06418178Recruiting · Phase 2
Dose Optimization of MDMA-Assisted Therapy for PTSD
- Enrollment
- 60Testimated
- Started
- 2025-06-03
- Sponsor
- Bronx VA Medical Center
Conditions Posttraumatic Stress Disorder
Matched “Midomafetamine” in the study’s intervention “Midomafetamine”
- NCT06954025Enrolling by invitation · Phase 2
High-Intensity Inpatient MDMA-Assisted Psychotherapy for PTSD
- Enrollment
- 20Testimated
- Started
- 2025-05-16
- Sponsor
- ARQ National Psychotrauma Centre
Conditions Posttraumatic Stress Disorder (PTSD)
Matched “MDMA” in the study’s intervention “High-intensity inpatient MDMA-assisted psychotherapy”
- NCT06884514Completed · Phase 1
Acute Effects of MDMA Co-administration on the Response to Psilocybin in Healthy Subjects
- Enrollment
- 24Tactual
- Started
- 2025-04-03
- Sponsor
- University Hospital, Basel, Switzerland
Conditions Healthy
Matched “3,4-Methylenedioxymethamphetamine” in the study’s intervention “3,4-Methylenedioxymethamphetamine”
- NCT05790239Recruiting · Phase 2
MDMA-Assisted Therapy for Veterans With Moderate to Severe Post Traumatic Stress Disorder
- Enrollment
- 40Testimated
- Started
- 2025-03-01
- Sponsor
- Stephen Robert Marder
Conditions Post Traumatic Stress Disorder
Matched “3,4-Methylenedioxymethamphetamine” in the study’s intervention “3,4-methylenedioxymethamphetamine”
- NCT05837845Recruiting · Phase 2
MDMA-assisted Cognitive Processing Therapy Versus Cognitive Processing Therapy for Veterans With Severe Posttraumatic Stress Disorder
- Enrollment
- 30Testimated
- Started
- 2025-02-10
- Sponsor
- Patricia Suppes
Conditions PTSD
Matched “MDMA” in the study’s intervention “MDMA”
Records from ClinicalTrials.gov (U.S. National Library of Medicine, NIH), API v2. A study is listed against a compound only when a verified name for that compound appears as a whole word in one of the study's own intervention names. A short code must appear as written, and a name the registry uses for something else (Aleph, a vaccine maker) is not matched. Title matches are not accepted. The matched name and the intervention text it matched are shown with every row.
Searched as MDMA · 3,4-Methylenedioxymethamphetamine · Midomafetamine. Run this search at the registry — it returns the unfiltered result, including studies this page rejected as belonging to a different molecule.
A registered trial is a protocol somebody filed with the registry. It is not a result, and nothing on this plate says whether MDMA worked.
X · Legal
Controlled-substance status
United States federal scheduling, read from the DEA records this archive holds and shown with the passage each was read from. Not legal advice, and not necessarily current.
As the DEA states it
Quoted whole. The badge above is a reading of these passages and adds nothing to them.
Schedule I - Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse.
Other regulatory records
Registers outside the DEA that hold an entry for MDMA — chemical-safety and national inventories, each naming itself. They are not scheduling decisions.
Schedule I shall consist of the drugs and other substances, by whatever official name, common or usual name, chemical name, or brand name designated, listed in this section. Each drug or substance has been assigned the DEA Controlled Substances Code Number set forth opposite it. ... Unless specifically excepted or unless listed in another schedule, any material, compound, mixture, or preparation, which contains any quantity of the following hallucinogenic substances, or which contains any of its salts, isomers, and salts of isomers whenever the existence of such salts, isomers, and salts of isomers is possible within the specific chemical designation (for purposes of this paragraph only, the…
Hazardous Substances Data Bank (HSDB)21 CFR 1308.11(d) (USDEA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 19, 2017: https://www.ecfr.gov
United States federal status only. State law differs, and so does the law of every other country — none of it is represented here. Scheduling changes, and this reflects the DEA records held by PubChem descriptive sections when the monograph was last harvested, not necessarily today. This is a record of what a database publishes, not legal advice.
XI · Literature
Sources behind this dossier
The papers this compound's values were read from, ranked by what each contributed. Not a review of the field.
Every paper below is one some value on this page came from — a binding constant, a passage of pharmacology or toxicology, or a measured duration. Each entry says what this archive took from it. Nothing else is claimed about any of them: the title is the study’s own account of itself, and a summary written here would be an assertion with no source behind it.
- 01
Setola V, Hufeisen SJ, Grande-Allen KJ et al. · Molecular pharmacology 2003
- · 12 measurements at 11 targets (Ki), strongest SERT at 7.14 pX
- 02
Pharmacological characterization of designer cathinones in vitro
Simmler LD, Buser TA, Donzelli M et al. · British journal of pharmacology 2013
- · 5 measurements at 4 targets (Ki), strongest D1 at 6.43 pX
- 03
Rothman RB, Baumann MH, Dersch CM et al. · Synapse (New York, N.Y.) 2001
- · 3 measurements at 3 targets (Ki), strongest SERT at 6.62 pX
- 04
Ben-Daniel R, Deuther-Conrad W, Scheunemann M et al. · Bioorganic & medicinal chemistry 2008
- · 2 measurements at 1 target (Ki), strongest SERT at 9.14 pX
- 05
Arikci D, Borgulya J, Straumann I et al. · Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 2026
- · 4.8 h
- 06
Straumann I, Vizeli P, Avedisian I et al. · Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 2026
- · Duration of acute subjective effects
- 07
Safety pharmacology of acute MDMA administration in healthy subjects
Vizeli P, Liechti ME · Journal of psychopharmacology (Oxford, England) 2017
- · 2 timed observations on the simulation plate
- 08
Farré M, Tomillero A, Pérez-Mañá C et al. · European neuropsychopharmacology : the journal of the European College of Neuropsychopharmacology 2015
- · Human Toxicity Excerpts
- 09
Rubio-Araiz A, Perez-Hernandez M, Urrutia A et al. · The international journal of neuropsychopharmacology 2014
- · Mechanism of Action
- 10
MDMA decreases the effects of simulated social rejection
Frye CG, Wardle MC, Norman GJ et al. · Pharmacology, biochemistry, and behavior 2014
- · Human Toxicity Excerpts
- 11
Barbosa DJ, Serrat R, Mirra S et al. · Toxicological sciences : an official journal of the Society of Toxicology 2014
- · Mechanism of Action
- 12
Pardo-Lozano R, Farré M, Yubero-Lahoz S et al. · PloS one 2012
- · Human Toxicity Excerpts
- 13
MDMA intoxication and verbal memory performance: a placebo-controlled pharmaco-MRI study
Kuypers KP, Wingen M, Heinecke A et al. · Journal of psychopharmacology (Oxford, England) 2011
- · Mechanism of Action
- 14
Mueller M, Kolbrich EA, Peters FT et al. · Therapeutic drug monitoring 2009
- · Biological Half-Life
- 15
Baumann MH, Zolkowska D, Kim I et al. · Drug metabolism and disposition: the biological fate of chemicals 2009
- · Biological Half-Life
- 16
Impaired cognitive performance in drug free users of recreational ecstasy (MDMA)
Kelly PA · Journal of neurology, neurosurgery, and psychiatry 2000
- · Human Toxicity Excerpts
- 17
Mas M, Farré M, de la Torre R et al. · The Journal of pharmacology and experimental therapeutics 1999
- · Biological Half-Life