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=CC2=C(OCO2)C=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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Reinforcing effects of MDMA ("ecstasy") in drug-naive and cocaine-trained rats. | 2001 |
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The many faces of ecstasy. | 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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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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Intravenous administration of ecstasy (3,4-methylendioxymethamphetamine) enhances cortical and striatal acetylcholine release in vivo. | 2001 Apr 27 |
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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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Rhabdomyolysis and 3,4 methylenedioxymethamphetamine in rheumatological practice. | 2001 Aug |
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Long-term effects of 'ecstasy' abuse on the human brain studied by FDG PET. | 2001 Aug |
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Pre-exposure to (+/-)3,4-methylenedioxy-methamphetamine (MDMA) facilitates acquisition of intravenous cocaine self-administration in rats. | 2001 Aug |
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Ecstasy experts want realistic messages. | 2001 Aug 15 |
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Changes in serotonin, dopamine and noradrenaline levels in striatum and nucleus accumbens after repeated administration of the abused drug MDMA in rats. | 2001 Aug 3 |
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The road to rave. | 2001 Aug 6 |
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[Multiple organ failure associated with use of ecstasy]. | 2001 Feb |
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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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Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans. | 2001 Feb 10 |
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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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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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Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats. | 2001 Feb 9 |
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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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The relative contributions of ecstasy and cannabis to cognitive impairment. | 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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Dextromethorphan and ecstasy pills. | 2001 Jan 24-31 |
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An "accidental" acute psychosis with ecstasy use. | 2001 Jan-Mar |
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MDMA. | 2001 Jul |
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Analysis of 4-methylthioamphetamine in clinical specimens. | 2001 Jul |
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Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase. | 2001 Jul |
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[Fatal brain edema after ingestion of ecstasy and benzylpiperazine]. | 2001 Jul 13 |
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Rave on. Ecstasy use continues to grow & present new problems for EMS. | 2001 Jun |
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A neurotoxic dose of 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) to rats results in a long-term defect in thermoregulation. | 2001 Jun |
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Vascular actions of MDMA involve alpha1 and alpha2-adrenoceptors in the anaesthetized rat. | 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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The effect of (R)-HA966 or ACEA 1021 on dexfenfluramine or (S)-MDMA-induced changes in temperature, activity, and neurotoxicity. | 2001 Mar |
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The use of drugs within the techno party scene in European metropolitan cities. | 2001 Mar |
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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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Development of a capillary electrophoresis-77 K luminescence detection system for online spectral identification. | 2001 Mar |
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Caveat emptor: editors beware. | 2001 Mar |
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Gender differences in the subjective effects of MDMA. | 2001 Mar 1 |
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Sensitive determination of methylenedioxylated amphetamines by liquid chromatography. | 2001 May |
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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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3,4-methylenedioxymethamphetamine (ecstasy)-induced learning and memory impairments depend on the age of exposure during early development. | 2001 May 1 |
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Poisoning with the recreational drug paramethoxyamphetamine ("death"). | 2001 May 7 |
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Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS. | 2001 May-Jun |
Patents
Substance Class |
Chemical
Created
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Sun Dec 18 19:59:00 UTC 2022
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Record UNII |
KE1SEN21RM
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WIKIPEDIA |
PiHKAL
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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
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PM 011
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DB01454
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PRIMARY | |||
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6929
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1615
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DTXSID90860791
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1391
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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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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET -> INHIBITOR |
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TARGET -> INHIBITOR |
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
IN-VIVO
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DERIVATIVE -> PARENT |
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LABELED -> NON-LABELED |
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE |
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TARGET -> INHIBITOR |
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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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