MDMA

3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in tablet form (ecstasy) and crystal form (molly),[14][15] is a psychoactive drug primarily used for recreational purposes.[16] The desired effects include altered sensations, increased energy, empathy, and pleasure.[16][17] When taken by mouth, effects begin in 30 to 45 minutes and last 3 to 6 hours.[12][18]

MDMA
INN: Midomafetamine[1]
Clinical data
Pronunciationmethylenedioxy­methamphetamine:
/ˌmɛθɪlndˈɒksi/
/ˌmɛθæmˈfɛtəmn/
Other names3,4-MDMA; Ecstasy (E, X, XTC); Molly; Mandy;[2][3] Pingers/Pingas[4]
AHFS/Drugs.comMDMA
Dependence
liability
Physical: not typical[5]
Psychological: moderate
Addiction
liability
Low–moderate[6][7][8]
Routes of
administration
Common: by mouth[9]
Uncommon: snorting,[9] inhalation (vaporization),[9] injection,[9][10] rectal
Drug classempathogen–entactogen
stimulant
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver, CYP450 extensively involved, including CYP2D6
MetabolitesMDA, HMMA, HMA, DHA, MDP2P, MDOH[11]
Onset of action30–45 minutes (by mouth)[12]
Elimination half-life(R)-MDMA: 5.8 ± 2.2 hours (variable)[13]
(S)-MDMA: 3.6 ± 0.9 hours (variable)[13]
Duration of action4–6 hours[7][12]
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
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)

MDMA was first developed in 1912 by Merck.[19] It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s.[17][18] MDMA is commonly associated with dance parties, raves, and electronic dance music.[20] It may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine.[17] In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population).[21] This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids.[21] 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.[22]

Short-term adverse effects include grinding of the teeth, blurred vision, sweating and a rapid heartbeat,[17] 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.[17] MDMA acts primarily by increasing the activity of the neurotransmitters serotonin, dopamine and noradrenaline in parts of the brain.[17][18] It belongs to the substituted amphetamine classes of drugs and has stimulant and hallucinogenic effects.[9][23]

MDMA is illegal in most countries[17][24] and has limited approved medical uses in a small number of countries.[9][25] In the United States, the Food and Drug Administration is currently evaluating the drug for clinical use.[26] Canada has allowed limited distribution of MDMA and other psychedelics such as psilocybin upon application to and approval by Health Canada.[27][28]


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