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
chemische verbinding
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 · Nederlands
De chemische stofnaam MDMA staat voor 3,4-methyleendioxymethamfetamine, een organische verbinding met als brutoformule C11H15NO2. MDMA en de verwante stoffen MDA, en MDEA zijn semisynthetische verbindingen die geclassificeerd worden als psychostimulantia en hallucinogenen. MDMA is een van de meestgebruikte synthetische drugs met name in de subcultuur van elektronische muziek (met name techno, trance, house en hardcore), maar het werd vroeger ook gebruikt bij psychotherapie. Gebruikers van MDMA ervaren geen lichamelijke verslaving en de psychisch verslavende werking is minder dan cocaine of methamfetamine. Ecstasy, xtc of X is de straatnaam voor pillen of poeders die onder meer de stof MDMA bevatten. Deze tabletten bevatten soms ook andere stoffen dan MDMA, bijvoorbeeld mCPP en PMMA. De stof MDMA staat sinds 1988 op Lijst 1 (harddrugs) van de Nederlandse Opiumwet. MDMA wordt in de scheikundig puurst mogelijke vorm verkocht in de vorm van zandkleurige kristallen. De Amerikaanse straatnaam voor MDMA (kristal) is molly. MDMA werd ontdekt en gepatenteerd door Merck in 1912 en in 1967 herontdekt door Alexander Shulgin, een scheikundige van University of California - Berkeley, die veel met het middel experimenteerde en gelijksoortige amfetaminen ontwikkelde.
Abstract from DBpedia / Wikipedia · CC BY-SA
Gallery (29)
Available in 68 languages
- Español
- Français
- Deutsch
- 中文
- 日本語
- Русский
- Português
- Italiano
- العربية
- हिन्दी
- Asturian
- azb
- Azerbaijani
- Bahasa Indonesia
- Bangla
- Basque
- Bavarian
- Bulgarian
Show 49 more
- Catalan
- Central Kurdish
- Croatian
- Czech
- Danish
- Egyptian Arabic
- Esperanto
- Estonian
- Faroese
- Finnish
- Galician
- gpe
- Greek
- Hebrew
- Hungarian
- Icelandic
- Irish
- Kashmiri
- Latin
- Latvian
- Limburgish
- Lithuanian
- Malagasy
- Malay
- Malayalam
- Nederlands
- Norwegian
- Norwegian Nynorsk
- Odia
- Polski
- Romanian
- Scots
- Serbian
- Serbian (Latin)
- simple
- Slovak
- Slovenian
- Svenska
- Swahili
- Tiếng Việt
- Türkçe
- Ukrainian
- Urdu
- Welsh
- Western Frisian
- Wu Chinese
- zh_yue
- فارسی
- 한국어
via Wikidata sitelinks · CC0