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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=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

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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Trace amine-associated receptor 1
47
Target ID: Q96RJ0
Gene ID: 134864.0
Gene Symbol: TAAR1
Target Organism: Homo sapiens (Human)
Activator
1430
Synaptic vesicular amine transporter
57
Target ID: Q05940
Gene ID: 6571.0
Gene Symbol: SLC18A2
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Agonist
2678
Inhibitor
8297
 405.0 nM [IC50]
Inhibitor
8297
 425.0 nM [IC50]
Inhibitor
8297
 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
Reinforcing effects of MDMA ("ecstasy") in drug-naive and cocaine-trained rats.
2001
Caveat emptor: editors beware.
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
Intravenous administration of ecstasy (3,4-methylendioxymethamphetamine) enhances cortical and striatal acetylcholine release in vivo.
2001 Apr 27
[Complications arising from occasional consumption of ecstasy].
2001 Aug
Party-drugs: sociocultural and individual background and risks.
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
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
[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
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
Causes of Alzheimer's disease: paracetamol (acetaminophen) today? Amphetamines tomorrow?
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
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
Ecstasy is a dangerous drug.
2001 Jun
Rave on. Ecstasy use continues to grow & present new problems for EMS.
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
Subjective effects of MDMA ('Ecstasy') on human sexual function.
2001 Mar
Sweat testing of MDMA with the Drugwipe analytical device: a controlled study with two volunteers.
2001 Mar
Effects of MDMA (ecstasy) on prepulse inhibition and habituation of startle in humans after pretreatment with citalopram, haloperidol, or ketanserin.
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
Long-term impairment of anterograde axonal transport along fiber projections originating in the rostral raphe nuclei after treatment with fenfluramine or methylenedioxymethamphetamine.
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
Application of solvent microextraction to the analysis of amphetamines and phencyclidine in urine.
2001 Sep 1
Patents

Patents

JP2009526755A
447
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
ACTIVE MOIETY
Structure of MIDOMAFETAMINE
METABOLITE (PARENT)
Structure of TENAMFETAMINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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