U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C11H15NO2
Molecular Weight 193.2427
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIDOMAFETAMINE

SMILES

CC(Cc1ccc2c(c1)OCO2)NC

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

HIDE SMILES / InChI

Molecular Formula C11H15NO2
Molecular Weight 193.2427
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

Curator's Comment:: MDMA was first synthesized by a German company in 1912, possibly to be used as an appetite suppressant.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q96RJ0
Gene ID: 134864
Gene Symbol: TAAR1
Target Organism: Homo sapiens (Human)
Target ID: Q05940
Gene ID: 6571
Gene Symbol: SLC18A2
Target Organism: Homo sapiens (Human)
405 nM [IC50]
425 nM [IC50]
1.43999999999999995 µM [IC50]
PubMed

PubMed

TitleDatePubMed
Reinforcing effects of MDMA ("ecstasy") in drug-naive and cocaine-trained rats.
2001
Involvement of free radicals in MDMA-induced neurotoxicity in mice.
2001 Apr
Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat.
2001 Apr
The many faces of ecstasy.
2001 Apr
Caveat emptor: editors beware.
2001 Apr
Ecstasy ingestion and fulminant hepatic failure: liver transplantation to be considered as a last therapeutic option.
2001 Apr
Pneumomediastinum in association with MDMA ingestion.
2001 Apr
Investigating the neurocognitive deficits associated with chronic drug misuse.
2001 Apr
Enhancement of 3,4-methylenedioxymethamphetamine neurotoxicity by the energy inhibitor malonate.
2001 Apr
Memory impairment in abstinent MDMA ("Ecstasy") users: a longitudinal investigation.
2001 Apr 10
[Fatal ecstasy intoxication].
2001 Apr 16
Methylenedioxymethamphetamine-induced suppression of interleukin-1beta and tumour necrosis factor-alpha is not mediated by serotonin.
2001 Apr 20
Intravenous administration of ecstasy (3,4-methylendioxymethamphetamine) enhances cortical and striatal acetylcholine release in vivo.
2001 Apr 27
Ecstasy crackdown. Will the feds use a 1980s anti-crack law to destroy the rave movement?
2001 Apr 9
[Complications arising from occasional consumption of ecstasy].
2001 Aug
Party-drugs: sociocultural and individual background and risks.
2001 Aug
Liver transplantation for ecstasy-induced fulminant hepatic failure.
2001 Aug
Long-term effects of 'ecstasy' abuse on the human brain studied by FDG PET.
2001 Aug
Is hyperthermia the triggering factor for hepatotoxicity induced by 3,4-methylenedioxymethamphetamine (ecstasy)? An in vitro study using freshly isolated mouse hepatocytes.
2001 Feb
Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans.
2001 Feb 10
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
Cracking down on ecstasy. Law enforcement is treating the 'hug drug' as if it were the next cocaine. Is it?
2001 Feb 5
Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats.
2001 Feb 9
Monitoring synthetic drug markets, trends, and public health.
2001 Jan
The relative contributions of ecstasy and cannabis to cognitive impairment.
2001 Jan
Addressing the threats of MDMA (Ecstasy): implications for school health professionals, parents, and community members.
2001 Jan
Dextromethorphan and ecstasy pills.
2001 Jan 24-31
An "accidental" acute psychosis with ecstasy use.
2001 Jan-Mar
Analysis of 4-methylthioamphetamine in clinical specimens.
2001 Jul
MDMA ("ecstasy") exhibits an anxiogenic-like activity in social encounters between male mice.
2001 Jul
Prejunctional actions of methylenedioxymethamphetamine in vas deferens from wild-type and alpha(2A/D)-adrenoceptor knockout mice.
2001 Jul 6
Quantitation of amphetamine-type compounds for which no reference compound is available: the validation of a theoretical model.
2001 Jul-Sep
Rave on. Ecstasy use continues to grow & present new problems for EMS.
2001 Jun
A neurotoxic dose of 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) to rats results in a long-term defect in thermoregulation.
2001 Jun
Ecstasy induced acute myocardial infarction.
2001 Jun
3,4-Methylenedioxymethamphetamine (MDMA) as a unique model of serotonin receptor function and serotonin-dopamine interactions.
2001 Jun
A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone.
2001 Jun 15
3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose.
2001 Mar
The use of drugs within the techno party scene in European metropolitan cities.
2001 Mar
Subjective effects of MDMA ('Ecstasy') on human sexual function.
2001 Mar
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.
2001 Mar
Sweat testing of MDMA with the Drugwipe analytical device: a controlled study with two volunteers.
2001 Mar
Development of a capillary electrophoresis-77 K luminescence detection system for online spectral identification.
2001 Mar
Sensitive determination of methylenedioxylated amphetamines by liquid chromatography.
2001 May
Recreational use of 3,4-methylenedioxymethamphetamine (MDMA) or 'ecstasy': evidence for cognitive impairment.
2001 May
Long-term impairment of anterograde axonal transport along fiber projections originating in the rostral raphe nuclei after treatment with fenfluramine or methylenedioxymethamphetamine.
2001 May
Poisoning with the recreational drug paramethoxyamphetamine ("death").
2001 May 7
Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS.
2001 May-Jun
Evaluation of Roche Abuscreen ONLINE amphetamine immunoassay for screening of new amphetamine analogues.
2001 Sep
Drug use and life style among college undergraduates: a 30-year longitudinal study.
2001 Sep
Patents
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:25:53 UTC 2021
Edited
by admin
on Sat Jun 26 03:25:53 UTC 2021
Record UNII
KE1SEN21RM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MIDOMAFETAMINE
INN   USAN  
USAN   INN  
Official Name English
MIDOMAFETAMINE [INN]
Common Name English
METHYLENEDIOXYMETHAMPHETAMINE [WHO-DD]
Common Name English
MDMA
MI  
Common Name English
3,4-METHYLENEDIOXYMETHAMPHETAMINE
Common Name English
(+/-)-N-METHYL-1-(3,4-METHYLENEDIOXYPHENYL)-2-AMINOPROPANE
Systematic Name English
(+/-)-(3,4-METHYLENEDIOXY)METHAMPHETAMINE
Common Name English
(RS)-1-(BENZO(D)(1,3)DIOXOL-5-YL)-N-METHYLPROPAN-2-AMINE
Systematic Name English
N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE [HSDB]
Common Name English
3,4-METHYLENEDIOXYMETAMPHETAMINE
Common Name English
METHYLENEDIOXYMETHAMFETAMINE
MART.  
Common Name English
METHYLENEDIOXYMETHAMFETAMINE [MART.]
Common Name English
D,L-3,4-METHYLENEDIOXYMETHAMPHETAMINE
Common Name English
XTC
Common Name English
METHYLENEDIOXYMETAMPHETAMINE
Common Name English
ECSTASY
Common Name English
1,3-BENZODIOXOLE-5-ETHANAMINE, N,.ALPHA.-DIMETHYL-
Systematic Name English
DL-(3,4-METHYLENEDIOXY)METHAMPHETAMINE
Common Name English
PHENETHYLAMINE, N,.ALPHA.-DIMETHYL-3,4-METHYLENEDIOXY-
Systematic Name English
MDMA [MI]
Common Name English
METHYLENEDIOXYMETHAMPHETAMINE
WHO-DD  
Common Name English
(+/-)-N,.ALPHA.-DIMETHYL-3,4-(METHYLENEDIOXY)PHENETHYLAMINE
Systematic Name English
MIDOMAFETAMINE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
DEA NO. 7405
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
LIVERTOX AMPHETAMINES
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C61081
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
INCB IDS CODE
PM 011
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
DRUG BANK
DB01454
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
HSDB
6929
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
PUBCHEM
1615
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
FDA UNII
KE1SEN21RM
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
INN
10442
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
CAS
54946-52-0
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
SUPERSEDED
EVMPD
SUB20716
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
WIKIPEDIA
MDMA
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
CAS
69610-10-2
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
SUPERSEDED
CAS
42542-10-9
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY
MERCK INDEX
M7106
Created by admin on Sat Jun 26 03:25:53 UTC 2021 , Edited by admin on Sat Jun 26 03:25:53 UTC 2021
PRIMARY Merck Index
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