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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: 134864.0
Gene Symbol: TAAR1
Target Organism: Homo sapiens (Human)
Target ID: Q05940
Gene ID: 6571.0
Gene Symbol: SLC18A2
Target Organism: Homo sapiens (Human)
405.0 nM [IC50]
425.0 nM [IC50]
1.44 µM [IC50]
PubMed

PubMed

TitleDatePubMed
Distinct features of seizures induced by cocaine and amphetamine analogs.
1999 Jul 21
Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons.
1999 Jun
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
Ecstasy ingestion and fulminant hepatic failure: liver transplantation to be considered as a last therapeutic option.
2001 Apr
Methylenedioxymethamphetamine-induced suppression of interleukin-1beta and tumour necrosis factor-alpha is not mediated by serotonin.
2001 Apr 20
[Complications arising from occasional consumption of ecstasy].
2001 Aug
Party-drugs: sociocultural and individual background and risks.
2001 Aug
Studies on the neuroprotective effect of the enantiomers of AR-A008055, a compound structurally related to clomethiazole, on MDMA ("ecstasy")-induced neurodegeneration in rat brain.
2001 Aug
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.
2001 Aug
Liver transplantation for ecstasy-induced fulminant hepatic failure.
2001 Aug
Ecstasy pill testing: harm minimization gone too far?
2001 Aug
Ecstasy experts want realistic messages.
2001 Aug 15
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
Fact, fiction, and function: mythmaking and the social construction of ecstasy use.
2001 Jan
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.
2001 Jan
Cognitive performance and serotonergic function in users of ecstasy.
2001 Jan 1
Recreational pharmaceuticals.
2001 Jan 15
MDMA.
2001 Jul
Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase.
2001 Jul
[Fatal brain edema after ingestion of ecstasy and benzylpiperazine].
2001 Jul 13
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
Prejunctional actions of methylenedioxymethamphetamine in vas deferens from wild-type and alpha(2A/D)-adrenoceptor knockout mice.
2001 Jul 6
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
A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone.
2001 Jun 15
Effects of methylenedioxymethamphetamine on noradrenaline-evoked contractions of rat right ventricle and small mesenteric artery.
2001 Jun 22
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
Caveat emptor: editors beware.
2001 Mar
Effects of MDMA (ecstasy) on prepulse inhibition and habituation of startle in humans after pretreatment with citalopram, haloperidol, or ketanserin.
2001 Mar
Biochemical effects of the monoamine neurotoxins DSP-4 and MDMA in specific brain regions of MAO-B-deficient mice.
2001 Mar 1
[A case of acute psychotic episode after a single dose of ecstasy].
2001 Mar-Apr
Recreational use of 3,4-methylenedioxymethamphetamine (MDMA) or 'ecstasy': evidence for cognitive impairment.
2001 May
Poisoning with the recreational drug paramethoxyamphetamine ("death").
2001 May 7
Application of solvent microextraction to the analysis of amphetamines and phencyclidine in urine.
2001 Sep 1
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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