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Methylenedioxymethamphetamine

MDMA
MDMA structure
Ball-and-stick model of an MDMA molecule
Clinical data
Pronunciation methylenedioxy­methamphetamine:
/ˈmɛ.θɪ.ln.d.ˈɒk.si./
/ˌmɛθæmˈfɛtəmn/
AHFS/Drugs.com MDMA
Dependence
liability
Physical: not typical
Psychological: moderate
Addiction
liability
Low–moderate
Routes of
administration
Common: by mouth
Uncommon: snorting,inhalation (vaporization),injection,rectal
Drug class empathogen–entactogen
stimulant
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Metabolism Liver, extensively involved, including CYP2D6
Metabolites MDA, HMMA, HMA, DHA, MDP2P, MDOH
Onset of action 30–45 minutes (by mouth)
Biological half-life (R)-MDMA: 5.8 ± 2.2 hours
(S)-MDMA: 3.6 ± 0.9 hours
Duration of action 4–6 hours
Excretion Kidney
Identifiers
Synonyms 3,4-MDMA, ecstasy (E, X, XTC), molly, mandy
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
Chemical and physical data
Formula C11H15NO2
Molar mass 193.25 g·mol−1
3D model (Jmol)
Chirality Racemic mixture
Boiling point 105 °C (221 °F) at 0.4 mmHg (experimental)
  

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (E), is a psychoactive drug used primarily as a recreational drug. Desired effects include increased empathy, euphoria, and heightened sensations. When taken by mouth, effects begin after 30–45 minutes and last 3–6 hours. It is also sometimes snorted or smoked. As of 2017, MDMA has no accepted medical uses.

Adverse effects of MDMA use include addiction, memory problems, paranoia, difficulty sleeping, teeth grinding, blurred vision, sweating, and a rapid heartbeat. Use may also lead to depression and fatigue. Deaths have been reported due to increased body temperature and dehydration. MDMA increases the release and slows the reuptake of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain. It has stimulant and psychedelic effects. The initial increase is followed by a short-term decrease in the neurotransmitters. MDMA belongs to the substituted methylenedioxyphenethylamine and substituted amphetamine classes of drugs.


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