Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H15NO2 |
Molecular Weight | 193.2423 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(C)CC1=CC=C2OCOC2=C1
InChI
InChIKey=SHXWCVYOXRDMCX-UHFFFAOYSA-N
InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3
Molecular Formula | C11H15NO2 |
Molecular Weight | 193.2423 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Methylenedioxymethamphetamine (or 3,4-methylenedioxymethamphetamine (MDMA)), a synthetic, psychoactive drug also known as ecstasy that was used as a recreational drug. This drug acts as both a stimulant and psychedelic and exerts its effects in the brain on neurons that use the chemicals serotonin, dopamine and norepinephrine to communicate with other neurons. In spite of the presence of this compound in the List of control and forbidden compounds, it was studied in psychotherapy for patients with chronic, treatment-resistant posttraumatic stress disorder. Initial results showed efficacy for the treatment approach, although further studies are needed.
Originator
Sources: https://www.drugs.com/illicit/mdma.html
Curator's Comment: MDMA was first synthesized by a German company in 1912, possibly to be used as an appetite suppressant.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q96RJ0 Gene ID: 134864.0 Gene Symbol: TAAR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21073468 |
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Target ID: Q05940 Gene ID: 6571.0 Gene Symbol: SLC18A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12742084 |
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Target ID: CHEMBL2096662 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7824160 |
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Target ID: CHEMBL222 |
405.0 nM [IC50] | ||
Target ID: CHEMBL228 |
425.0 nM [IC50] | ||
Target ID: CHEMBL238 Sources: https://www.drugbank.ca/drugs/DB01454 |
1.44 µM [IC50] |
PubMed
Title | Date | PubMed |
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Acute injection of drugs with low addictive potential (delta(9)-tetrahydrocannabinol, 3,4-methylenedioxymethamphetamine, lysergic acid diamide) causes a much higher c-fos expression in limbic brain areas than highly addicting drugs (cocaine and morphine). | 1999 Aug 25 |
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Distinct features of seizures induced by cocaine and amphetamine analogs. | 1999 Jul 21 |
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Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons. | 1999 Jun |
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Prior experience of morphine application alters the c-fos response to MDMA ('ecstasy') and cocaine in the rat striatum. | 2000 Apr 14 |
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Involvement of free radicals in MDMA-induced neurotoxicity in mice. | 2001 Apr |
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Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat. | 2001 Apr |
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Caveat emptor: editors beware. | 2001 Apr |
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Ecstasy ingestion and fulminant hepatic failure: liver transplantation to be considered as a last therapeutic option. | 2001 Apr |
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Pneumomediastinum in association with MDMA ingestion. | 2001 Apr |
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Investigating the neurocognitive deficits associated with chronic drug misuse. | 2001 Apr |
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Enhancement of 3,4-methylenedioxymethamphetamine neurotoxicity by the energy inhibitor malonate. | 2001 Apr |
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Ascorbic acid prevents 3,4-methylenedioxymethamphetamine (MDMA)-induced hydroxyl radical formation and the behavioral and neurochemical consequences of the depletion of brain 5-HT. | 2001 Apr |
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Memory impairment in abstinent MDMA ("Ecstasy") users: a longitudinal investigation. | 2001 Apr 10 |
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Methylenedioxymethamphetamine-induced suppression of interleukin-1beta and tumour necrosis factor-alpha is not mediated by serotonin. | 2001 Apr 20 |
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Ecstasy crackdown. Will the feds use a 1980s anti-crack law to destroy the rave movement? | 2001 Apr 9 |
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[Complications arising from occasional consumption of ecstasy]. | 2001 Aug |
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Is hyperthermia the triggering factor for hepatotoxicity induced by 3,4-methylenedioxymethamphetamine (ecstasy)? An in vitro study using freshly isolated mouse hepatocytes. | 2001 Feb |
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No difference in brain activation during cognitive performance between ecstasy (3,4-methylenedioxymethamphetamine) users and control subjects: a [H2(15)O]-positron emission tomography study. | 2001 Feb |
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Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans. | 2001 Feb 10 |
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Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model. | 2001 Feb 15 |
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[Young woman dies of water intoxication after taking one tablet of ecstasy. Today's drug panorama calls for increased vigilance in health care]. | 2001 Feb 21 |
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Case records of the Massachusetts General Hospital. Weekly clinicopathological exercises. Case 6-2001. A 17-year-old girl with marked jaundice and weight loss. | 2001 Feb 22 |
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Cracking down on ecstasy. Law enforcement is treating the 'hug drug' as if it were the next cocaine. Is it? | 2001 Feb 5 |
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Monitoring synthetic drug markets, trends, and public health. | 2001 Jan |
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Fact, fiction, and function: mythmaking and the social construction of ecstasy use. | 2001 Jan |
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Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine. | 2001 Jan |
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Addressing the threats of MDMA (Ecstasy): implications for school health professionals, parents, and community members. | 2001 Jan |
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Cognitive performance and serotonergic function in users of ecstasy. | 2001 Jan 1 |
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Dextromethorphan and ecstasy pills. | 2001 Jan 24-31 |
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MDMA ("ecstasy") exhibits an anxiogenic-like activity in social encounters between male mice. | 2001 Jul |
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Prejunctional actions of methylenedioxymethamphetamine in vas deferens from wild-type and alpha(2A/D)-adrenoceptor knockout mice. | 2001 Jul 6 |
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Rave on. Ecstasy use continues to grow & present new problems for EMS. | 2001 Jun |
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A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone. | 2001 Jun 15 |
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Effects of methylenedioxymethamphetamine on noradrenaline-evoked contractions of rat right ventricle and small mesenteric artery. | 2001 Jun 22 |
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Subjective effects of MDMA ('Ecstasy') on human sexual function. | 2001 Mar |
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Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis. | 2001 Mar |
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Sweat testing of MDMA with the Drugwipe analytical device: a controlled study with two volunteers. | 2001 Mar |
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Caveat emptor: editors beware. | 2001 Mar |
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Long-term impairment of anterograde axonal transport along fiber projections originating in the rostral raphe nuclei after treatment with fenfluramine or methylenedioxymethamphetamine. | 2001 May |
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PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA. | 2001 May-Jun |
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The mechanisms involved in the long-lasting neuroprotective effect of fluoxetine against MDMA ('ecstasy')-induced degeneration of 5-HT nerve endings in rat brain. | 2001 Sep |
Patents
Substance Class |
Chemical
Created
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Wed Apr 02 08:52:19 GMT 2025
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KE1SEN21RM
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Validated (UNII)
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Classification Tree | Code System | Code | ||
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WIKIPEDIA |
PiHKAL
Created by
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NCI_THESAURUS |
C47795
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DEA NO. |
7405
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LIVERTOX |
AMPHETAMINES
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Code System | Code | Type | Description | ||
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C61081
Created by
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PM 011
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DB01454
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6929
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1615
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DTXSID90860791
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1391
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100000175884
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CD-122
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KE1SEN21RM
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10442
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54946-52-0
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SUB20716
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MDMA
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69610-10-2
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42542-10-9
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m7106
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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PRECURSOR->PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET -> INHIBITOR |
Inhibition of [3H]Neurotransmitter Uptake
IC50
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TARGET -> INHIBITOR |
Inhibition of [3H]Neurotransmitter Uptake
IC50
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
IC50
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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PRECURSOR->PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
IN-VIVO
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DERIVATIVE -> PARENT |
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PRECURSOR->PARENT |
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LABELED -> NON-LABELED |
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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PRECURSOR->PARENT |
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SALT/SOLVATE -> PARENT |
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ENANTIOMER -> RACEMATE |
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR |
Inhibition of [3H]Neurotransmitter Uptake. May reverse flow of serotonin leading to release.
IC50
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ENANTIOMER -> RACEMATE |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
PLASMA
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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