MDMA

MDMA
INN: Midomafetamine
Skeletal structures of (R)-MDMA (top) and (S)-MDMA (bottom)
Ball-and-stick models of (R)-MDMA (top) and (S)-MDMA (bottom)
Clinical data
Pronunciationmethylenedioxy­methamphetamine:
/ˌmɛθɪlndˈɒksi/
/ˌmɛθæmˈfɛtəmn/
Other names3,4-MDMA; Ecstasy (E, X, XTC); Midomafetamine; Molly; Mandy; Pingers/Pingas
AHFS/Drugs.comMDMA
Dependence
liability
Physical: Not typical
Psychological: Moderate
Addiction
liability
Low–moderate
Routes of
administration
Common: By mouth
Uncommon: Insufflation, inhalation, injection, rectal
Drug classEntactogen; Stimulant; Psychedelic; Serotonin–norepinephrine–dopamine releasing agent; Serotonin 5-HT2 receptor agonist
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: Unknown
Protein bindingUnknown
MetabolismLiver, CYP450 extensively involved, including CYP2D6
MetabolitesMDA, HMMA, HMA, HHMA, HHA, THMA, THA, MDP2P, MDOH
Onset of actionOral: 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 action3–6 hours
ExcretionKidney
Identifiers
  • (RS)-1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H15NO2
Molar mass193.246 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Density1.1 g/cm3
Boiling point105 °C (221 °F) at 0.4 mmHg (experimental)
  • CC(NC)CC1=CC=C(OCO2)C2=C1
  • 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 (tablet form), and molly (crystal form), is an empathogen–entactogenic drug with stimulant and minor psychedelic properties. In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder. 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.

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). This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids. 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.

Short-term adverse effects include grinding of the teeth, blurred vision, sweating, and a rapid heartbeat, and extended use can also lead to addiction, memory problems, paranoia, and difficulty sleeping. Deaths have been reported due to increased body temperature and dehydration. Following use, people often feel depressed and tired, although this effect does not appear in clinical use, suggesting that it is not a direct result of MDMA administration. 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. In the United States, the Food and Drug Administration (FDA) is evaluating the drug for clinical use as of 2021. 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.