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Details

Stereochemistry RACEMIC
Molecular Formula C11H15NO2.ClH
Molecular Weight 229.7036
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MIDOMAFETAMINE HYDROCHLORIDE

SMILES

CC(Cc1ccc2c(c1)OCO2)NC.Cl

InChI

InChIKey=LUWHVONVCYWRMZ-UHFFFAOYSA-N
InChI=1S/C11H15NO2.ClH/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;1H

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 ( + / - )

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Reinforcing effects of MDMA ("ecstasy") in drug-naive and cocaine-trained rats.
2001
Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat.
2001 Apr
The many faces of ecstasy.
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
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
Rhabdomyolysis and 3,4 methylenedioxymethamphetamine in rheumatological practice.
2001 Aug
Ecstasy pill testing: harm minimization gone too far?
2001 Aug
Pre-exposure to (+/-)3,4-methylenedioxy-methamphetamine (MDMA) facilitates acquisition of intravenous cocaine self-administration in rats.
2001 Aug
On-line identification of 3,4-methylenedioxymethamphetamine in human urine by non-aqueous capillary electrophoresis-fluorescence spectroscopy at 77 K.
2001 Aug 15
The road to rave.
2001 Aug 6
[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
The relative contributions of ecstasy and cannabis to cognitive impairment.
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
MDMA.
2001 Jul
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
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
3,4-Methylenedioxymethamphetamine (ecstasy)-induced hepatotoxicity: multidetector CT and pathology findings.
2001 Jul-Aug
Rave on. Ecstasy use continues to grow & present new problems for EMS.
2001 Jun
Designer drugs. Assess & manage patients intoxicated with ecstasy, GHB or rohypnol--the three most commonly abused designer drugs.
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
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
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
Caveat emptor: editors beware.
2001 Mar
[A case of acute psychotic episode after a single dose of ecstasy].
2001 Mar-Apr
Sensitive determination of methylenedioxylated amphetamines by liquid chromatography.
2001 May
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
Effects of ecstasy (MDMA) on the brain in abstinent users: initial observations with diffusion and perfusion MR imaging.
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 Fri Jun 25 22:08:21 UTC 2021
Edited
by admin
on Fri Jun 25 22:08:21 UTC 2021
Record UNII
KNB4E1K0AV
Record Status Validated (UNII)
Record Version
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Name Type Language
MIDOMAFETAMINE HYDROCHLORIDE
Common Name English
NSC-168383
Code English
MDMA HYDROCHLORIDE [INCB:GREEN LIST]
Common Name English
METHYLENEDIOXYMETHAMPHETAMINE HYDROCHLORIDE
Common Name English
3,4-METHYLENEDIOXY-N,.ALPHA.-DIMETHYL-.BETA.-PHENYLETHYLAMINE HYDROCHLORIDE
Systematic Name English
MDMA HYDROCHLORIDE [MI]
Common Name English
MDMA HYDROCHLORIDE
INCB:GREEN LIST   MI  
Common Name English
1,3-BENZODIOXOLE-5-ETHANAMINE, N,.ALPHA.-DIMETHYL-, HYDROCHLORIDE
Systematic Name English
3,4-METHYLENEDIOXYMETHAMPHETAMINE HYDROCHLORIDE
Common Name English
PHENETHYLAMINE, N,.ALPHA.-DIMETHYL-3,4-METHYLENEDIOXY-, HYDROCHLORIDE
Systematic Name English
MDMA HCL
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT002574
Created by admin on Fri Jun 25 22:08:21 UTC 2021 , Edited by admin on Fri Jun 25 22:08:21 UTC 2021
PRIMARY
CAS
64057-70-1
Created by admin on Fri Jun 25 22:08:21 UTC 2021 , Edited by admin on Fri Jun 25 22:08:21 UTC 2021
PRIMARY
PUBCHEM
71285
Created by admin on Fri Jun 25 22:08:21 UTC 2021 , Edited by admin on Fri Jun 25 22:08:21 UTC 2021
PRIMARY
EPA CompTox
64057-70-1
Created by admin on Fri Jun 25 22:08:21 UTC 2021 , Edited by admin on Fri Jun 25 22:08:21 UTC 2021
PRIMARY
MERCK INDEX
M7106
Created by admin on Fri Jun 25 22:08:21 UTC 2021 , Edited by admin on Fri Jun 25 22:08:21 UTC 2021
PRIMARY Merck Index
EVMPD
SUB127825
Created by admin on Fri Jun 25 22:08:21 UTC 2021 , Edited by admin on Fri Jun 25 22:08:21 UTC 2021
PRIMARY
FDA UNII
KNB4E1K0AV
Created by admin on Fri Jun 25 22:08:21 UTC 2021 , Edited by admin on Fri Jun 25 22:08:21 UTC 2021
PRIMARY
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