File:MDMA_structure.svg · Wikimedia Commons · See Wikimedia Commons
MDMA
Sign in to saveAlso known as 3,4-methylenedioxymethamphetamine, N,alpha-dimethyl-1,3-benzodioxole-5-ethanamine, (RS)-3,4-(methylenedioxy)methamphetamine, DL-(3,4-Methylenedioxy)methamphetamine, ecstasy, Molly, Mandy, Adam
molécule psychostimulante de la classe des amphétamines
OverviewAI-generated
MDMA is a chemical compound with the formula C₁₁H₁₅NO₂. Its IUPAC name is 1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine. The substance has a boiling point of 155 and a mass of 193.110279.
Chemical properties include a weight of 193.24, an xlogp of 2.2, and a tpsa of 30.5. The molecule contains one hydrogen bond donor and three hydrogen bond acceptors, with a charge of 0. It is referenced by 4,321 other encyclopedia articles.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 632164040
- Drug.drug_name
- MDMA
- Drug.INN
- Midomafetamine
- Drug.image
- MDMA structure.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 235px
- Drug.alt
- MDMA structure
- Drug.caption
- Skeletal structure of racemic MDMA
- Drug.image2
- MDMA molecule from xtal ball.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of MDMA molecule enantiomers
- Drug.width2
- 225px
- Drug.caption2
- Ball-and-stick model of MDMA
- Drug.pronounce
- methylenedioxymethamphetamine:
- Drug.routes_of_administration
- Common: By mouth Uncommon: Insufflation, inhalation, injection, rectal
- Drug.class
- Entactogen; Stimulant; Psychedelic; Serotonin–norepinephrine–dopamine releasing agent; 5-HT2 receptor agonist
- Drug.dependency_liability
- Physical: Not typicalPsychological: Moderate
via Wikipedia infobox
Chemical data
- Formula
- C11H15NO2
- Molecular weight
- 193.24 g/mol
- IUPAC name
- 1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
- SMILES
- CC(CC1=CC2=C(C=C1)OCO2)NC
- InChIKey
- SHXWCVYOXRDMCX-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 30.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- post-traumatic stress disorder, drug dependence, liver disease, autism spectrum disorder
via ChEMBL · EBI
Research
6,654 papers- Neurotoxicity of MDMA: Main effects and mechanisms.Experimental neurology · 2022
- MDMA interactions with pharmaceuticals and drugs of abuse.Expert opinion on drug metabolism & toxicology · 2020
- [MDMA-assisted therapy for PTSD].Laeknabladid · 2024
- MDMA-Assisted Psychotherapy for Treatment of Posttraumatic Stress Disorder: A Systematic Review With Meta-Analysis.Journal of clinical pharmacology · 2022
- MDMA related neuro-inflammation and adenosine receptors.Neurochemistry international · 2022
via PubMed
Wikidata facts
- Subclass of
- amphetamines
- Has part
- oxygen
- Mass
- 193.110279
- Image
- Ecstasy-02.jpg
Show 11 more facts
- short name
- MDMA
- Commons category
- MDMA
- chemical formula
- C₁₁H₁₅NO₂
- physically interacts with
- Solute carrier family 18 member A2
- boiling point
- 115
- subject has role
- stimulant
- canonical SMILES
- CC(CC1=CC2=C(C=C1)OCO2)NC
- discoverer or inventor
- Anton Köllisch
- route of administration
- insufflation
- found in taxon
- Caenorhabditis elegans
- described by source
- Phenethylamines I Have Known And Loved
Sources (10)
via Wikidata · CC0
Article · Français
La MDMA (pour 3,4-méthylènedioxy-N-méthylamphétamine) est une amine sympathicomimétique, molécule psychostimulante de la classe des amphétamines. Puissant sympathicomimétique et sérotoninergique, la MDMA est souvent utilisée comme drogue, vendue alors sous forme de cristaux (souvent impurs) ou de pilules sous le nom d'ecstasy (de teneur variable en principe actif). Ces produits ne contiennent souvent pas que de la MDMA mais aussi des molécules proches telles que des sous-produits de synthèse (MDA ou MBDB) ou des analogues de synthèse comme la méthylone. La MDMA est un stimulant du système nerveux central qui possède des caractéristiques psychotropes particulières, qualifiées par certains auteurs d'entactogènes. C'est également un puissant sérotoninergique, ce qui le transforme à fortes doses, ou en cas d'usage régulier, en un neurotoxique. Elle est particulièrement répandue dans le milieu festif, fréquemment associée au mouvement techno, aux rave parties et à la musique électronique. La MDMA est classée comme stupéfiant en France, et listée sur la convention sur les substances psychotropes de 1971.
Abstract from DBpedia / Wikipedia · CC BY-SA
Gallery (29)
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