Methylenedioxymethamphetamine

MDMA

Clinical data
Pronunciation	methylenedioxy­methamphetamine: /ˈmɛ.θɪ.liːn.daɪ.ˈɒk.si./ /ˌmɛθæmˈfɛtəmiːn/
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	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) NZ: Class B UK: Class A US: Schedule I UN: Psychotropic Schedule I
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
IUPAC name (RS)-1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
Synonyms	3,4-MDMA, ecstasy (E, X, XTC), molly, mandy
CAS Number	42542-10-9 Y[TOXNET]
PubChem CID	1615
IUPHAR/BPS	4574
DrugBank	DB01454 Y
ChemSpider	1556 Y
UNII	KE1SEN21RM
KEGG	C07577 Y
ChEBI	CHEBI:1391 Y
ChEMBL	CHEMBL43048 Y
PDB ligand	B41 (PDBe, RCSB PDB)
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.25 g·mol−1
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
Boiling point	105 °C (221 °F) at 0.4 mmHg (experimental)
SMILES CC(NC)CC1=CC=C(OCO2)C2=C1
InChI InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3 Y Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N Y

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^[update], 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.