MIDOMAFETAMINE

Investigational

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24648791 | https://www.drugs.com/illicit/mdma.html

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Trace amine-associated receptor 1 48 Target ID: Q96RJ0 Gene ID: 134864.0 Gene Symbol: TAAR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21073468	Activator 1447
Synaptic vesicular amine transporter 57 Target ID: Q05940 Gene ID: 6571.0 Gene Symbol: SLC18A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12742084	Inhibitor 8504
Serotonin 2 receptors; 5-HT2a & 5-HT2c 7 Target ID: CHEMBL2096662 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7824160	Agonist 2752
Norepinephrine transporter 197 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20466553 \| https://www.ncbi.nlm.nih.gov/pubmed/19717215	Inhibitor 8504	405.0 nM [IC50]
Serotonin transporter 183 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20466553 \| https://www.ncbi.nlm.nih.gov/pubmed/19717215	Inhibitor 8504	425.0 nM [IC50]
Dopamine transporter 183 Target ID: CHEMBL238 Sources: https://www.drugbank.ca/drugs/DB01454	Inhibitor 8504	1.44 µM [IC50]

PubMed

Title	Date	PubMed
Application of solvent microextraction to the analysis of amphetamines and phencyclidine in urine.	2001-09-01	11473798
Evaluation of Roche Abuscreen ONLINE amphetamine immunoassay for screening of new amphetamine analogues.	2001-09	11550823
Drug use and life style among college undergraduates: a 30-year longitudinal study.	2001-09	11532744
Effects of ecstasy (MDMA) on the brain in abstinent users: initial observations with diffusion and perfusion MR imaging.	2001-09	11526257
The mechanisms involved in the long-lasting neuroprotective effect of fluoxetine against MDMA ('ecstasy')-induced degeneration of 5-HT nerve endings in rat brain.	2001-09	11522596
Quantitation of amphetamine-type compounds for which no reference compound is available: the validation of a theoretical model.	2001-08-23	11515165
On-line identification of 3,4-methylenedioxymethamphetamine in human urine by non-aqueous capillary electrophoresis-fluorescence spectroscopy at 77 K.	2001-08-15	11499475
Ecstasy experts want realistic messages.	2001-08-15	11497515
The road to rave.	2001-08-06	11499276
Changes in serotonin, dopamine and noradrenaline levels in striatum and nucleus accumbens after repeated administration of the abused drug MDMA in rats.	2001-08-03	11457569
[Complications arising from occasional consumption of ecstasy].	2001-08	11530758
Party-drugs: sociocultural and individual background and risks.	2001-08	11515712
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.	2001-08	11512047
Rhabdomyolysis and 3,4 methylenedioxymethamphetamine in rheumatological practice.	2001-08	11508609
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.	2001-08	11505218
Liver transplantation for ecstasy-induced fulminant hepatic failure.	2001-08	11498145
Ecstasy pill testing: harm minimization gone too far?	2001-08	11487420
Long-term effects of 'ecstasy' abuse on the human brain studied by FDG PET.	2001-08	11473208
Pre-exposure to (+/-)3,4-methylenedioxy-methamphetamine (MDMA) facilitates acquisition of intravenous cocaine self-administration in rats.	2001-08	11425503
3,4-Methylenedioxymethamphetamine (ecstasy)-induced hepatotoxicity: multidetector CT and pathology findings.	2001-07-27	11473199
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").	2001-07-15	11526995
[Fatal brain edema after ingestion of ecstasy and benzylpiperazine].	2001-07-13	11499262
Prejunctional actions of methylenedioxymethamphetamine in vas deferens from wild-type and alpha(2A/D)-adrenoceptor knockout mice.	2001-07-06	11448488
MDMA.	2001-07	11511457
Analysis of 4-methylthioamphetamine in clinical specimens.	2001-07	11471875
Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase.	2001-07	11453733
MDMA ("ecstasy") exhibits an anxiogenic-like activity in social encounters between male mice.	2001-07	11428907
PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA.	2001-06-23	11420094
Effects of methylenedioxymethamphetamine on noradrenaline-evoked contractions of rat right ventricle and small mesenteric artery.	2001-06-22	11430927
[A case of acute psychotic episode after a single dose of ecstasy].	2001-06-16	11407274
A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone.	2001-06-15	11376983
Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS.	2001-06-02	11386639
Ecstasy is a dangerous drug.	2001-06	11508041
Rave on. Ecstasy use continues to grow & present new problems for EMS.	2001-06	11452955
A neurotoxic dose of 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) to rats results in a long-term defect in thermoregulation.	2001-06	11441431
Designer drugs. Assess & manage patients intoxicated with ecstasy, GHB or rohypnol--the three most commonly abused designer drugs.	2001-06	11409205
Vascular actions of MDMA involve alpha1 and alpha2-adrenoceptors in the anaesthetized rat.	2001-06	11375260
Ecstasy induced acute myocardial infarction.	2001-06	11359764
3,4-Methylenedioxymethamphetamine (MDMA) as a unique model of serotonin receptor function and serotonin-dopamine interactions.	2001-06	11356903
Poisoning with the recreational drug paramethoxyamphetamine ("death").	2001-05-07	11386590
Sensitive determination of methylenedioxylated amphetamines by liquid chromatography.	2001-05	11394297
Recreational use of 3,4-methylenedioxymethamphetamine (MDMA) or 'ecstasy': evidence for cognitive impairment.	2001-05	11352367
Intravenous administration of ecstasy (3,4-methylendioxymethamphetamine) enhances cortical and striatal acetylcholine release in vivo.	2001-04-27	11343691
[Fatal ecstasy intoxication].	2001-04-16	11344662
Involvement of free radicals in MDMA-induced neurotoxicity in mice.	2001-04	11435997
Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat.	2001-04	11371001
Spontaneous pneumomediastinum, pneumothorax and ecstasy abuse.	2001-03	11476403
3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose.	2001-03	11351932
Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats.	2001-02-09	11388689
[Multiple organ failure associated with use of ecstasy].	2001-02	11345602

Patents

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

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Name

Type

Language

MDMA	Locators: MI Sources:

Preferred Name

English

MIDOMAFETAMINE

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

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

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