MDMA

For other uses, see MDMA (disambiguation). Not to be confused with MDA (drug); EDMA; NMDA; 2,3-MDMA; MDNA; or NDMA.

MDMA
INN: Midomafetamine

Skeletal structure of racemic MDMA
Ball-and-stick model of MDMA
Clinical data
Pronunciation	methylenedioxy­methamphetamine: /ˌmɛθɪliːndaɪˈɒksi/ /ˌmɛθæmˈfɛtəmiːn/
Other names	3,4-MDMA; Ecstasy (E, X, XTC); Midomafetamine; Molly; Mandy; Pingers/Pingas
AHFS/Drugs.com	MDMA
Dependence liability	Physical: Not typical Psychological: Moderate
Addiction liability	Low–moderate
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
ATC code	None
Legal status
Legal status	AU: S8 (PTSD) S9 (all other uses) BR: Class F2 (Prohibited psychotropics) CA: Schedule I DE: Anlage I (Authorized scientific use only) NZ: Class B UK: Class A US: Schedule I UN: Psychotropic Schedule I EU: Fully prohibited SE: Förteckning I
Pharmacokinetic data
Bioavailability	Oral: Unknown
Protein binding	Unknown
Metabolism	Liver, CYP450 extensively involved, including CYP2D6
Metabolites	MDA, HMMA, HMA, HHMA, HHA, THMA, THA, MDP2P, MDOH 3-MMOTI
Onset of action	Oral: 30–45 min
Elimination half-life	MDMA: 8.7 (range 4.6–16) hours (S)-MDMA: 5.1 (range 3.5–7.4) hours (R)-MDMA: 11 (range 5.1–24) hours
Duration of action	3–6 hours
Excretion	Kidney
Identifiers
IUPAC name (RS)-1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
CAS Number	42542-10-9 Y[TOXNET] 64057-70-1 (HCl)
PubChem CID	1615
IUPHAR/BPS	4574
DrugBank	DB01454 Y
ChemSpider	1556 Y
UNII	KE1SEN21RM
KEGG	D11172 Y
ChEBI	CHEBI:1391 Y
ChEMBL	ChEMBL43048 Y
PDB ligand	B41 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)	DTXSID90860791
Chemical and physical data
Formula	C11H15NO2
Molar mass	193.246 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
Density	1.1 g/cm3
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
(verify)

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy in tablet form, and molly in 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 used by attendees of dance parties, raves, and electronic dance music festivals. Tablets sold as ecstasy may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine.

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.

The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure. When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours. Short-term adverse effects include bruxism, blurred vision, sweating, and tachycardia, and extended use can also lead to addiction, amnesia, memory disorders, paranoia, and insomnia. Deaths have been reported due to increased body temperature and dehydration. MDMA acts primarily by increasing the release of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain. It belongs to the substituted amphetamine classes of drugs. MDMA is structurally similar to mescaline (a psychedelic), methamphetamine (a stimulant), as well as endogenous monoamine neurotransmitters such as serotonin, norepinephrine, and dopamine.

MDMA has limited approved medical uses in a small number of countries, but is illegal in most jurisdictions. MDMA-assisted psychotherapy may substantially improve PTSD symptoms, response, and remission rates compared to psychotherapy alone, but the evidence is low to very low certainty and safety data are limited, with some increased transient adverse events. In the United States, the Food and Drug Administration (FDA) has given MDMA breakthrough therapy status (though there are no current clinical indications in the US). Canada has allowed limited distribution of MDMA upon application to and approval by Health Canada. In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.