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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=CC=C2OCOC2=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 ( + / - )

Description

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

German company
2
Curator's Comment: MDMA was first synthesized by a German company in 1912, possibly to be used as an appetite suppressant.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Trace amine-associated receptor 1
48
Target ID: Q96RJ0
Gene ID: 134864.0
Gene Symbol: TAAR1
Target Organism: Homo sapiens (Human)
Activator
1447
Synaptic vesicular amine transporter
57
Target ID: Q05940
Gene ID: 6571.0
Gene Symbol: SLC18A2
Target Organism: Homo sapiens (Human)
Inhibitor
8504
Agonist
2752
Inhibitor
8504
 405.0 nM [IC50]
Inhibitor
8504
 425.0 nM [IC50]
Inhibitor
8504
 1.44 µM [IC50]
PubMed

PubMed

TitleDatePubMed
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
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
Prior experience of morphine application alters the c-fos response to MDMA ('ecstasy') and cocaine in the rat striatum.
2000 Apr 14
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
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
Ascorbic acid prevents 3,4-methylenedioxymethamphetamine (MDMA)-induced hydroxyl radical formation and the behavioral and neurochemical consequences of the depletion of brain 5-HT.
2001 Apr
Memory impairment in abstinent MDMA ("Ecstasy") users: a longitudinal investigation.
2001 Apr 10
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
[Complications arising from occasional consumption of ecstasy].
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
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
Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans.
2001 Feb 10
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.
2001 Feb 15
[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
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
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
Addressing the threats of MDMA (Ecstasy): implications for school health professionals, parents, and community members.
2001 Jan
Cognitive performance and serotonergic function in users of ecstasy.
2001 Jan 1
Dextromethorphan and ecstasy pills.
2001 Jan 24-31
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
Rave on. Ecstasy use continues to grow & present new problems for EMS.
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
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
Caveat emptor: editors beware.
2001 Mar
Long-term impairment of anterograde axonal transport along fiber projections originating in the rostral raphe nuclei after treatment with fenfluramine or methylenedioxymethamphetamine.
2001 May
PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA.
2001 May-Jun
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
Patents

Patents

JP2009526755A
475
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:52:19 GMT 2025
Edited
by admin
on Wed Apr 02 08:52:19 GMT 2025
Record UNII
KE1SEN21RM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MDMA
MI  
Preferred Name English
MIDOMAFETAMINE
INN   USAN  
USAN   INN  
Official Name English
midomafetamine [INN]
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 Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
NCI_THESAURUS C47795
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
DEA NO. 7405
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
LIVERTOX AMPHETAMINES
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C61081
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
INCB IDS CODE
PM 011
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
DRUG BANK
DB01454
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
HSDB
6929
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
PUBCHEM
1615
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
EPA CompTox
DTXSID90860791
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
CHEBI
1391
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
SMS_ID
100000175884
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
USAN
CD-122
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
FDA UNII
KE1SEN21RM
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
INN
10442
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
CAS
54946-52-0
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
SUPERSEDED
EVMPD
SUB20716
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
WIKIPEDIA
MDMA
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
CAS
69610-10-2
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
SUPERSEDED
CAS
42542-10-9
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY
MERCK INDEX
m7106
Created by admin on Wed Apr 02 08:52:19 GMT 2025 , Edited by admin on Wed Apr 02 08:52:19 GMT 2025
PRIMARY Merck Index
Related Record Type Details
ISOSAFROLE
PRECURSOR->PARENT
CYTOCHROME P450 2B6
METABOLIC ENZYME -> SUBSTRATE
MAJOR
SODIUM-DEPENDENT DOPAMINE TRANSPORTER
TARGET -> INHIBITOR
Inhibition of [3H]Neurotransmitter Uptake
IC50
SODIUM-DEPENDENT NORADRENALINE TRANSPORTER
TARGET -> INHIBITOR
Inhibition of [3H]Neurotransmitter Uptake
IC50
OCT-1
TRANSPORTER -> INHIBITOR
Chromaffin granule amine transporter
TRANSPORTER -> INHIBITOR
IC50
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
Structure of PMK METHYL GLYCIDATE
PRECURSOR->PARENT
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
IN-VIVO
Structure of 6-CHLORO-MDMA
DERIVATIVE -> PARENT
Structure of Methylamine
PRECURSOR->PARENT
Structure of MIDOMAFETAMINE, (N-METHYL-D3)-
LABELED -> NON-LABELED
OCT-3
TRANSPORTER -> INHIBITOR
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Structure of 3,4-METHYLENEDIOXYPHENYL-2-PROPANONE
PRECURSOR->PARENT
Structure of Midomafetamine Hydrochloride
SALT/SOLVATE -> PARENT
Structure of MIDOMAFETAMINE, (R)-
ENANTIOMER -> RACEMATE
OCT-2
TRANSPORTER -> INHIBITOR
SODIUM-DEPENDENT SEROTONIN TRANSPORTER
TARGET -> INHIBITOR
Inhibition of [3H]Neurotransmitter Uptake. May reverse flow of serotonin leading to release.
IC50
Structure of MIDOMAFETAMINE, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of 4-HYDROXY-3-METHOXYMETHAMPHETAMINE-4-O-SULFATE
METABOLITE -> PARENT
PLASMA
Structure of 3,4-DIHYDROXYMETHAMPHETAMINE-3-O-SULFATE
METABOLITE -> PARENT
PLASMA
Structure of 3,4-DIHYDROXYMETHAMPHETAMINE-4-O-SULFATE
METABOLITE -> PARENT
PLASMA
Structure of 3,4-DIHYDROXYMETHAMPHETAMINE
METABOLITE -> PARENT
Structure of 4-HYDROXY-3-METHOXYMETHAMPHETAMINE
METABOLITE -> PARENT
Structure of TENAMFETAMINE
METABOLITE -> PARENT
PLASMA
Structure of 4-HYDROXY-3-METHOXYMETHAMPHETAMINE-4-BETA-D-GLUCURONIDE
METABOLITE -> PARENT
PLASMA
Related Record Type Details
Structure of MIDOMAFETAMINE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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