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=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 1410
Synaptic vesicular amine transporter 56 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 8228
Serotonin 2 receptors; 5-HT2a & 5-HT2c 7 Target ID: CHEMBL2096662 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7824160	Agonist 2662
Norepinephrine transporter 190 Target ID: CHEMBL222 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20466553 \| https://www.ncbi.nlm.nih.gov/pubmed/19717215	Inhibitor 8228	405.0 nM [IC50]
Serotonin transporter 177 Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20466553 \| https://www.ncbi.nlm.nih.gov/pubmed/19717215	Inhibitor 8228	425.0 nM [IC50]
Dopamine transporter 179 Target ID: CHEMBL238 Sources: https://www.drugbank.ca/drugs/DB01454	Inhibitor 8228	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
Involvement of free radicals in MDMA-induced neurotoxicity in mice.	2001 Apr	11435997
The many faces of ecstasy.	2001 Apr	11317061
Caveat emptor: editors beware.	2001 Apr	11310414
Pneumomediastinum in association with MDMA ingestion.	2001 Apr	11303526
Investigating the neurocognitive deficits associated with chronic drug misuse.	2001 Apr	11301247
Enhancement of 3,4-methylenedioxymethamphetamine neurotoxicity by the energy inhibitor malonate.	2001 Apr	11299327
Memory impairment in abstinent MDMA ("Ecstasy") users: a longitudinal investigation.	2001 Apr 10	11294938
Ecstasy pill testing: harm minimization gone too far?	2001 Aug	11487420
Long-term effects of 'ecstasy' abuse on the human brain studied by FDG PET.	2001 Aug	11473208
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
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	11207356
Alterations in diurnal and nocturnal locomotor activity in rats treated with a monoamine-depleting regimen of methamphetamine or 3,4-methylenedioxymethamphetamine.	2001 Jan	11271404
Acute effects of 3,4-methylenedioxymethamphetamine alone and in combination with ethanol on the immune system in humans.	2001 Jan	11123382
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
Ecstasy induced acute myocardial infarction.	2001 Jun	11359764
Effects of methylenedioxymethamphetamine on noradrenaline-evoked contractions of rat right ventricle and small mesenteric artery.	2001 Jun 22	11430927
The use of drugs within the techno party scene in European metropolitan cities.	2001 Mar	11316921
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
Gender differences in the subjective effects of MDMA.	2001 Mar 1	11314678
[A case of acute psychotic episode after a single dose of ecstasy].	2001 Mar-Apr	11407274
3,4-methylenedioxymethamphetamine (ecstasy)-induced learning and memory impairments depend on the age of exposure during early development.	2001 May 1	11312307
Profiles of urine samples taken from Ecstasy users at Rave parties: analysis by immunoassays, HPLC, and GC-MS.	2001 May-Jun	11386639
Effects of ecstasy (MDMA) on the brain in abstinent users: initial observations with diffusion and perfusion MR imaging.	2001 Sep	11526257

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

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

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

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METABOLIC ENZYME -> SUBSTRATE

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SODIUM-DEPENDENT NORADRENALINE TRANSPORTER

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TRANSPORTER -> INHIBITOR


					8E4LAA4357

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METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

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Amount:


					6G65JU3BBZ

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DERIVATIVE -> PARENT

Amount:


					BSF23SJ79E

METHYLAMINE

PRECURSOR->PARENT

Amount:


					482M00274D

OCT-2

TRANSPORTER -> INHIBITOR


					6AK7RRC64B

MIDOMAFETAMINE, (N-METHYL-D3)-

LABELED -> NON-LABELED

Amount:


					ONY583280Z

OCT-1

TRANSPORTER -> INHIBITOR


					VK4SQL11C0

CYTOCHROME P450 1A2

METABOLIC ENZYME -> SUBSTRATE

Interaction Type:

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Amount:


					PNA80F81BT

3,4-METHYLENEDIOXYPHENYL-2-PROPANONE

PRECURSOR->PARENT

Amount:


					KNB4E1K0AV

MIDOMAFETAMINE HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Amount:


					3947754WXW

MIDOMAFETAMINE, (R)-

ENANTIOMER -> RACEMATE

Amount:


					CJZ26L1EGI

SODIUM-DEPENDENT SEROTONIN TRANSPORTER

TARGET -> INHIBITOR

Amount:


					9B6GK297FN

MIDOMAFETAMINE, (S)-

ENANTIOMER -> RACEMATE

Amount:

Related Record Type Details


					FI7RY2GH5X

4-HYDROXY-3-METHOXYMETHAMPHETAMINE-4-O-SULFATE

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:


					T0X1I0QX62

3,4-DIHYDROXYMETHAMPHETAMINE-3-O-SULFATE

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:


					CQZ6LFU8HQ

3,4-DIHYDROXYMETHAMPHETAMINE-4-O-SULFATE

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:


					VFV03WN1VN

3,4-DIHYDROXYMETHAMPHETAMINE

METABOLITE -> PARENT

Amount:


					RBY3J6H4JW

4-HYDROXY-3-METHOXYMETHAMPHETAMINE

METABOLITE -> PARENT

Amount:


					XJZ28FJ27W

TENAMFETAMINE

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:


					WPP3V4F887

4-HYDROXY-3-METHOXYMETHAMPHETAMINE-4-BETA-D-GLUCURONIDE

METABOLITE -> PARENT

Qualification:

PLASMA

Amount:

Related Record Type Details


					KE1SEN21RM

MIDOMAFETAMINE

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

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

Originator

Approval Year

Targets

PubMed

Patents

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