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MDMA

File:MDMA_structure.svg · Wikimedia Commons · See Wikimedia Commons

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MDMA

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Also 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

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an entactogen with stimulant and minor psychedelic properties.

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

Research

6,654 papers

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

~63 min read

Encyclopedic overview

51 sections
Contents
  • Uses
  • Recreational
  • Medical
  • Others
  • Forms
  • Effects
  • Side effects
  • Short-term
  • Long-term
  • Reinforcement disorders
  • During pregnancy
  • Overdose
  • Interactions
  • Pharmacology
  • Pharmacodynamics
  • Pharmacokinetics
  • Absorption
  • Distribution
  • Metabolism
  • Elimination
  • Chemistry
  • Properties
  • Synthesis
  • Detection in body fluids
  • Analogues
  • History
  • Early research and use
  • Shulgin's research
  • Rising recreational use
  • Media attention and scheduling
  • United States
  • United Nations
  • Post-scheduling
  • Society and culture
  • Legal status
  • Australia
  • Canada
  • Finland
  • Netherlands
  • United Kingdom
  • United States
  • Demographics
  • Economics
  • Europe
  • North America
  • Australia
  • Corporate logos on pills
  • Research
  • See also
  • References
  • External links

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an entactogen with stimulant and minor psychedelic properties.

MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch. It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s. MDMA is commonly associated with dance parties, raves, and electronic dance music. Tablets sold as ecstasy may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine. In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population). In the United States, as of 2017, about 7% of people have used MDMA at some point in their lives and 0.9% have used it in the last year. The lethal risk from one dose of MDMA is estimated to be from 1 death in 20,000 instances to 1 death in 50,000 instances.

Excerpted from Wikipedia’s “MDMA” article, available under the CC BY-SA 4.0 licence.

Gallery (29)

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via Wikidata sitelinks · CC0