MIDOMAFETAMINE

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=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	( + / - )

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 47 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 1404
Synaptic vesicular amine transporter 53 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 8146
Serotonin 2 receptors; 5-HT2a & 5-HT2c 7 Target ID: CHEMBL2096662 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7824160	Agonist 2637
Norepinephrine transporter 183 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20466553 \| https://www.ncbi.nlm.nih.gov/pubmed/19717215	Inhibitor 8146	405.0 nM [IC50]
Serotonin transporter 172 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20466553 \| https://www.ncbi.nlm.nih.gov/pubmed/19717215	Inhibitor 8146	425.0 nM [IC50]
Dopamine transporter 172 Target ID: CHEMBL238 Sources: https://www.drugbank.ca/drugs/DB01454	Inhibitor 8146	1.44 µM [IC50]

PubMed

Title	Date	PubMed
Reinforcing effects of MDMA ("ecstasy") in drug-naive and cocaine-trained rats.	2001	11287814
The many faces of ecstasy.	2001 Apr	11317061
Caveat emptor: editors beware.	2001 Apr	11310414
Ecstasy ingestion and fulminant hepatic failure: liver transplantation to be considered as a last therapeutic option.	2001 Apr	11308131
Pneumomediastinum in association with MDMA ingestion.	2001 Apr	11303526
Investigating the neurocognitive deficits associated with chronic drug misuse.	2001 Apr	11301247
Memory impairment in abstinent MDMA ("Ecstasy") users: a longitudinal investigation.	2001 Apr 10	11294938
Methylenedioxymethamphetamine-induced suppression of interleukin-1beta and tumour necrosis factor-alpha is not mediated by serotonin.	2001 Apr 20	11334877
Intravenous administration of ecstasy (3,4-methylendioxymethamphetamine) enhances cortical and striatal acetylcholine release in vivo.	2001 Apr 27	11343691
Ecstasy crackdown. Will the feds use a 1980s anti-crack law to destroy the rave movement?	2001 Apr 9	11301990
Rhabdomyolysis and 3,4 methylenedioxymethamphetamine in rheumatological practice.	2001 Aug	11508609
Long-term effects of 'ecstasy' abuse on the human brain studied by FDG PET.	2001 Aug	11473208
Pre-exposure to (+/-)3,4-methylenedioxy-methamphetamine (MDMA) facilitates acquisition of intravenous cocaine self-administration in rats.	2001 Aug	11425503
Ecstasy experts want realistic messages.	2001 Aug 15	11497515
Changes in serotonin, dopamine and noradrenaline levels in striatum and nucleus accumbens after repeated administration of the abused drug MDMA in rats.	2001 Aug 3	11457569
The road to rave.	2001 Aug 6	11499276
[Multiple organ failure associated with use of ecstasy].	2001 Feb	11345602
Is hyperthermia the triggering factor for hepatotoxicity induced by 3,4-methylenedioxymethamphetamine (ecstasy)? An in vitro study using freshly isolated mouse hepatocytes.	2001 Feb	11305782
Stereospecific analysis of ecstasy-like N-ethyl-3,4-methylenedioxyamphetamine and its metabolites in humans.	2001 Feb 10	11232860
[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	11265566
Cracking down on ecstasy. Law enforcement is treating the 'hug drug' as if it were the next cocaine. Is it?	2001 Feb 5	11211524
Prior exposure to methylenedioxyamphetamine (MDA) induces serotonergic loss and changes in spontaneous exploratory and amphetamine-induced behaviors in rats.	2001 Feb 9	11388689
Monitoring synthetic drug markets, trends, and public health.	2001 Jan	11305353
Fact, fiction, and function: mythmaking and the social construction of ecstasy use.	2001 Jan	11305347
The relative contributions of ecstasy and cannabis to cognitive impairment.	2001 Jan	11271410
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.	2001 Jan	11271404
Addressing the threats of MDMA (Ecstasy): implications for school health professionals, parents, and community members.	2001 Jan	11221539
Dextromethorphan and ecstasy pills.	2001 Jan 24-31	11242417
An "accidental" acute psychosis with ecstasy use.	2001 Jan-Mar	11333007
MDMA.	2001 Jul	11511457
Analysis of 4-methylthioamphetamine in clinical specimens.	2001 Jul	11471875
Serotonergic neurotoxicity of 3,4-(+/-)-methylenedioxyamphetamine and 3,4-(+/-)-methylendioxymethamphetamine (ecstasy) is potentiated by inhibition of gamma-glutamyl transpeptidase.	2001 Jul	11453733
[Fatal brain edema after ingestion of ecstasy and benzylpiperazine].	2001 Jul 13	11499262
Rave on. Ecstasy use continues to grow & present new problems for EMS.	2001 Jun	11452955
A neurotoxic dose of 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) to rats results in a long-term defect in thermoregulation.	2001 Jun	11441431
Vascular actions of MDMA involve alpha1 and alpha2-adrenoceptors in the anaesthetized rat.	2001 Jun	11375260
A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone.	2001 Jun 15	11376983
The effect of (R)-HA966 or ACEA 1021 on dexfenfluramine or (S)-MDMA-induced changes in temperature, activity, and neurotoxicity.	2001 Mar	11325413
The use of drugs within the techno party scene in European metropolitan cities.	2001 Mar	11316921
Subjective effects of MDMA ('Ecstasy') on human sexual function.	2001 Mar	11311178
Analysis of amphetamine and congeners in illicit samples by liquid chromatography and capillary electrophoresis.	2001 Mar	11300514
Sweat testing of MDMA with the Drugwipe analytical device: a controlled study with two volunteers.	2001 Mar	11300507
Development of a capillary electrophoresis-77 K luminescence detection system for online spectral identification.	2001 Mar	11284330
Caveat emptor: editors beware.	2001 Mar	11256359
Gender differences in the subjective effects of MDMA.	2001 Mar 1	11314678
Sensitive determination of methylenedioxylated amphetamines by liquid chromatography.	2001 May	11394297
Long-term impairment of anterograde axonal transport along fiber projections originating in the rostral raphe nuclei after treatment with fenfluramine or methylenedioxymethamphetamine.	2001 May	11252022
3,4-methylenedioxymethamphetamine (ecstasy)-induced learning and memory impairments depend on the age of exposure during early development.	2001 May 1	11312307
Poisoning with the recreational drug paramethoxyamphetamine ("death").	2001 May 7	11386590
Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS.	2001 May-Jun	11386639

Patents

Substance Class	Chemical Created by `admin` on `Sun Dec 18 19:59:00 UTC 2022` Edited by `admin` on `Sun Dec 18 19:59:00 UTC 2022`
Record UNII	KE1SEN21RM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MIDOMAFETAMINE

Official Name

English

midomafetamine [INN]

Common Name

English

MDMA	Locators: MI Sources:

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