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
Hepatorenal problems presented in an urban high dependancy unit in a user of ecstasy and cocaine.
2000 Jan
Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat.
2001 Apr
Ecstasy ingestion and fulminant hepatic failure: liver transplantation to be considered as a last therapeutic option.
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
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
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
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.
2001 Aug
Ecstasy experts want realistic messages.
2001 Aug 15
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.
2001 Feb 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
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
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.
2001 Jan
Effect of the repeated administration of (+/-)-3,4-methylenedioxymethamphetamine on the behavioral response of rats to the 5-HT1A receptor agonist (+/-)-8-hydroxy-(di-n-propylamino)tetralin.
2001 Jan
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.
2001 Jan
Cognitive performance and serotonergic function in users of ecstasy.
2001 Jan 1
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
Designer drugs. Assess & manage patients intoxicated with ecstasy, GHB or rohypnol--the three most commonly abused designer drugs.
2001 Jun
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
Development of a capillary electrophoresis-77 K luminescence detection system for online spectral identification.
2001 Mar
Functional consequences of repeated (+/-)3,4-methylenedioxymethamphetamine (MDMA) treatment in rhesus monkeys.
2001 Mar
[A case of acute psychotic episode after a single dose of ecstasy].
2001 Mar-Apr
Patents
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:39:03 UTC 2023
Edited
by admin
on Thu Jul 06 22:39:03 UTC 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 Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
NCI_THESAURUS C47795
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
DEA NO. 7405
Created by admin on Thu Jul 06 22:39:06 UTC 2023 , Edited by admin on Thu Jul 06 22:39:06 UTC 2023
LIVERTOX AMPHETAMINES
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C61081
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
INCB IDS CODE
PM 011
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
DRUG BANK
DB01454
Created by admin on Thu Jul 06 22:39:06 UTC 2023 , Edited by admin on Thu Jul 06 22:39:06 UTC 2023
PRIMARY
HSDB
6929
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
PUBCHEM
1615
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
EPA CompTox
DTXSID90860791
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
CHEBI
1391
Created by admin on Thu Jul 06 22:39:06 UTC 2023 , Edited by admin on Thu Jul 06 22:39:06 UTC 2023
PRIMARY
SMS_ID
100000175884
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
USAN
CD-122
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
FDA UNII
KE1SEN21RM
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
INN
10442
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
CAS
54946-52-0
Created by admin on Thu Jul 06 22:39:06 UTC 2023 , Edited by admin on Thu Jul 06 22:39:06 UTC 2023
SUPERSEDED
EVMPD
SUB20716
Created by admin on Thu Jul 06 22:39:06 UTC 2023 , Edited by admin on Thu Jul 06 22:39:06 UTC 2023
PRIMARY
WIKIPEDIA
MDMA
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY
CAS
69610-10-2
Created by admin on Thu Jul 06 22:39:06 UTC 2023 , Edited by admin on Thu Jul 06 22:39:06 UTC 2023
SUPERSEDED
CAS
42542-10-9
Created by admin on Thu Jul 06 22:39:06 UTC 2023 , Edited by admin on Thu Jul 06 22:39:06 UTC 2023
PRIMARY
MERCK INDEX
M7106
Created by admin on Thu Jul 06 22:39:07 UTC 2023 , Edited by admin on Thu Jul 06 22:39:07 UTC 2023
PRIMARY Merck Index
Related Record Type Details
PRECURSOR->PARENT
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
PRECURSOR->PARENT
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
IN-VIVO
DERIVATIVE -> PARENT
PRECURSOR->PARENT
TRANSPORTER -> INHIBITOR
LABELED -> NON-LABELED
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
MAJOR
PRECURSOR->PARENT
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
TARGET -> INHIBITOR
ENANTIOMER -> RACEMATE
Related Record Type Details
METABOLITE -> PARENT
PLASMA
METABOLITE -> PARENT
PLASMA
METABOLITE -> PARENT
PLASMA
METABOLITE -> PARENT
METABOLITE -> PARENT
METABOLITE -> PARENT
PLASMA
METABOLITE -> PARENT
PLASMA
Related Record Type Details
ACTIVE MOIETY