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 1430
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 8297
Serotonin 2 receptors; 5-HT2a & 5-HT2c 7 Target ID: CHEMBL2096662 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7824160	Agonist 2678
Norepinephrine transporter 191 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20466553 \| https://www.ncbi.nlm.nih.gov/pubmed/19717215	Inhibitor 8297	405.0 nM [IC50]
Serotonin transporter 178 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20466553 \| https://www.ncbi.nlm.nih.gov/pubmed/19717215	Inhibitor 8297	425.0 nM [IC50]
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.drugbank.ca/drugs/DB01454	Inhibitor 8297	1.44 µM [IC50]

PubMed

Title	Date	PubMed
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	10521585
Distinct features of seizures induced by cocaine and amphetamine analogs.	1999 Jul 21	10456426
Amphetamines induce apoptosis and regulation of bcl-x splice variants in neocortical neurons.	1999 Jun	10336889
Prior experience of morphine application alters the c-fos response to MDMA ('ecstasy') and cocaine in the rat striatum.	2000 Apr 14	10814832
Hepatorenal problems presented in an urban high dependancy unit in a user of ecstasy and cocaine.	2000 Jan	11147017
[Case report: acute poisoning with ecstasy].	2000 Oct	11144740
Reinforcing effects of MDMA ("ecstasy") in drug-naive and cocaine-trained rats.	2001	11287814
Effect of GBR 12909 and fluoxetine on the acute and long term changes induced by MDMA ('ecstasy') on the 5-HT and dopamine concentrations in mouse brain.	2001	11077072
Involvement of free radicals in MDMA-induced neurotoxicity in mice.	2001 Apr	11435997
Behavioural, hyperthermic and neurotoxic effects of 3,4-methylenedioxymethamphetamine analogues in the Wistar rat.	2001 Apr	11371001
Pneumomediastinum in association with MDMA ingestion.	2001 Apr	11303526
Intravenous administration of ecstasy (3,4-methylendioxymethamphetamine) enhances cortical and striatal acetylcholine release in vivo.	2001 Apr 27	11343691
[Complications arising from occasional consumption of ecstasy].	2001 Aug	11530758
Party-drugs: sociocultural and individual background and risks.	2001 Aug	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 Aug	11512047
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.	2001 Aug	11505218
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
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	11199950
Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model.	2001 Feb 15	11160413
Addressing the threats of MDMA (Ecstasy): implications for school health professionals, parents, and community members.	2001 Jan	11221539
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	11150898
Causes of Alzheimer's disease: paracetamol (acetaminophen) today? Amphetamines tomorrow?	2001 Jan	11133268
Acute effects of 3,4-methylenedioxymethamphetamine alone and in combination with ethanol on the immune system in humans.	2001 Jan	11123382
Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin.	2001 Jan	11071707
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	11526995
Prejunctional actions of methylenedioxymethamphetamine in vas deferens from wild-type and alpha(2A/D)-adrenoceptor knockout mice.	2001 Jul 6	11448488
Quantitation of amphetamine-type compounds for which no reference compound is available: the validation of a theoretical model.	2001 Jul-Sep	11515165
A neurotoxic dose of 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) to rats results in a long-term defect in thermoregulation.	2001 Jun	11441431
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
Subjective effects of MDMA ('Ecstasy') on human sexual function.	2001 Mar	11311178
Caveat emptor: editors beware.	2001 Mar	11256359
Functional consequences of repeated (+/-)3,4-methylenedioxymethamphetamine (MDMA) treatment in rhesus monkeys.	2001 Mar	11166514
[A case of acute psychotic episode after a single dose of ecstasy].	2001 Mar-Apr	11407274
Evaluation of Roche Abuscreen ONLINE amphetamine immunoassay for screening of new amphetamine analogues.	2001 Sep	11550823
Drug use and life style among college undergraduates: a 30-year longitudinal study.	2001 Sep	11532744
Effects of ecstasy (MDMA) on the brain in abstinent users: initial observations with diffusion and perfusion MR imaging.	2001 Sep	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 Sep	11522596

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:14:56 GMT 2023` Edited by `admin` on `Sat Dec 16 17:14:56 GMT 2023`
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