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

Details

Stereochemistry RACEMIC
Molecular Formula C11H15NO2
Molecular Weight 193.2423
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIDOMAFETAMINE

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

HIDE SMILES / InChI

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

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
Involvement of free radicals in MDMA-induced neurotoxicity in mice.
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
[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
Ecstasy crackdown. Will the feds use a 1980s anti-crack law to destroy the rave movement?
2001 Apr 9
Party-drugs: sociocultural and individual background and risks.
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
Long-term effects of 'ecstasy' abuse on the human brain studied by FDG PET.
2001 Aug
Pre-exposure to (+/-)3,4-methylenedioxy-methamphetamine (MDMA) facilitates acquisition of intravenous cocaine self-administration in rats.
2001 Aug
Ecstasy experts want realistic messages.
2001 Aug 15
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
[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
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
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
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
Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase.
2001 Jul
MDMA ("ecstasy") exhibits an anxiogenic-like activity in social encounters between male mice.
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
3,4-Methylenedioxymethamphetamine (ecstasy)-induced hepatotoxicity: multidetector CT and pathology findings.
2001 Jul-Aug
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
Designer drugs. Assess & manage patients intoxicated with ecstasy, GHB or rohypnol--the three most commonly abused designer drugs.
2001 Jun
Effects of methylenedioxymethamphetamine on noradrenaline-evoked contractions of rat right ventricle and small mesenteric artery.
2001 Jun 22
Spontaneous pneumomediastinum, pneumothorax and ecstasy abuse.
2001 Mar
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 effect of (R)-HA966 or ACEA 1021 on dexfenfluramine or (S)-MDMA-induced changes in temperature, activity, and neurotoxicity.
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
Gender differences in the subjective effects of MDMA.
2001 Mar 1
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
3,4-methylenedioxymethamphetamine (ecstasy)-induced learning and memory impairments depend on the age of exposure during early development.
2001 May 1
Poisoning with the recreational drug paramethoxyamphetamine ("death").
2001 May 7
PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA.
2001 May-Jun
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
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
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 Dec 16 17:14:56 GMT 2023
Edited
by admin
on Sat Dec 16 17:14:56 GMT 2023
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
MDMA
MI  
Common Name English
3,4-METHYLENEDIOXYMETHAMPHETAMINE
Common Name English
(±)-N-METHYL-1-(3,4-METHYLENEDIOXYPHENYL)-2-AMINOPROPANE
Systematic Name English
MANDY
Common 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
Midomafetamine [WHO-DD]
Common Name English
3,4-METHYLENEDIOXYMETAMPHETAMINE
Common Name English
METHYLENEDIOXYMETHAMFETAMINE
MART.  
Common Name English
METHYLENEDIOXYMETHAMFETAMINE [MART.]
Common Name English
MOLLY
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
WIKIPEDIA PiHKAL
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
NCI_THESAURUS C47795
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
DEA NO. 7405
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
LIVERTOX AMPHETAMINES
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C61081
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
INCB IDS CODE
PM 011
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
DRUG BANK
DB01454
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
HSDB
6929
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
PUBCHEM
1615
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID90860791
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
CHEBI
1391
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
SMS_ID
100000175884
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
USAN
CD-122
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
FDA UNII
KE1SEN21RM
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
INN
10442
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
CAS
54946-52-0
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
SUPERSEDED
EVMPD
SUB20716
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
WIKIPEDIA
MDMA
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
CAS
69610-10-2
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
SUPERSEDED
CAS
42542-10-9
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY
MERCK INDEX
m7106
Created by admin on Sat Dec 16 17:14:59 GMT 2023 , Edited by admin on Sat Dec 16 17:14:59 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PRECURSOR->PARENT
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
PRECURSOR->PARENT
METABOLIC ENZYME -> SUBSTRATE
IN-VIVO
DERIVATIVE -> PARENT
PRECURSOR->PARENT
TRANSPORTER -> INHIBITOR
LABELED -> NON-LABELED
METABOLIC ENZYME -> SUBSTRATE
MAJOR
PRECURSOR->PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
ENANTIOMER -> RACEMATE
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
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METABOLITE -> PARENT
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METABOLITE -> PARENT
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METABOLITE -> PARENT
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METABOLITE -> PARENT
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ACTIVE MOIETY