MDMA

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

• 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

via Wikidata · CC0