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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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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Involvement of free radicals in MDMA-induced neurotoxicity in mice. | 2001 Apr |
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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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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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Memory impairment in abstinent MDMA ("Ecstasy") users: a longitudinal investigation. | 2001 Apr 10 |
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Ecstasy pill testing: harm minimization gone too far? | 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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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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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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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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Acute effects of 3,4-methylenedioxymethamphetamine alone and in combination with ethanol on the immune system in humans. | 2001 Jan |
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Repeated intermittent administration of psychomotor stimulant drugs alters the acquisition of Pavlovian approach behavior in rats: differential effects of cocaine, d-amphetamine and 3,4- methylenedioxymethamphetamine ("Ecstasy"). | 2001 Jul 15 |
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Ecstasy induced acute myocardial infarction. | 2001 Jun |
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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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The use of drugs within the techno party scene in European metropolitan cities. | 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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Gender differences in the subjective effects of MDMA. | 2001 Mar 1 |
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[A case of acute psychotic episode after a single dose of ecstasy]. | 2001 Mar-Apr |
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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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Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS. | 2001 May-Jun |
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Effects of ecstasy (MDMA) on the brain in abstinent users: initial observations with diffusion and perfusion MR imaging. | 2001 Sep |
Patents
Substance Class |
Chemical
Created
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Thu Jul 06 22:39:03 UTC 2023
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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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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 |
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLIC ENZYME -> SUBSTRATE |
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PRECURSOR->PARENT |
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TRANSPORTER -> INHIBITOR | |||
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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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TRANSPORTER -> INHIBITOR | |||
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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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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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