MDMA
Psychoactive drug / From Wikipedia, the free encyclopedia
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3,4-Methyl
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| Pronunciation | methylenedioxymethamphetamine: /ˌmɛθɪliːndaɪˈɒksi/ /ˌmɛθæmˈfɛtəmiːn/ |
| Other names | 3,4-MDMA; Ecstasy (E, X, XTC); Molly; Mandy;[2][3] Pingers/Pingas[4] |
| AHFS/Drugs.com | MDMA |
| 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 class | Empathogen–entactogen stimulant |
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| Bioavailability | Oral: Unknown[11] |
| Metabolism | Liver, CYP450 extensively involved, including CYP2D6 |
| Metabolites | MDA, HMMA, HMA, DHA, MDP2P, MDOH[12] |
| Onset of action | 30–45 minutes (by mouth)[11] |
| Elimination half-life | (R)-MDMA: 5.8 ± 2.2 hours (variable)[13] (S)-MDMA: 3.6 ± 0.9 hours (variable)[13] |
| Duration of action | 4–6 hours[7][11] |
| Excretion | Kidney |
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| Formula | C11H15NO2 |
| Molar mass | 193.246 g·mol−1 |
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| Chirality | Racemic mixture |
| Boiling point | 105 °C (221 °F) at 0.4 mmHg (experimental) |
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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] Tablets sold as ecstasy 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] 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.[23]
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, although this effect does not appear in clinical use, suggesting that it is not a direct result of MDMA administration.[17][24] MDMA acts primarily by increasing the release of the neurotransmitters serotonin, dopamine and noradrenaline in parts of the brain.[17][18] It belongs to the substituted amphetamine classes of drugs.[9][25] MDMA is structurally similar to mescaline (a hallucinogen), methamphetamine (a stimulant), as well as endogenous monoamine neurotransmitters such as serotonin, norepinephrine, and dopamine.[26]
MDMA is illegal in most countries[17][27] and has limited approved medical uses in a small number of countries.[9][28] In the United States, the Food and Drug Administration is currently evaluating the drug for clinical use.[29] Canada has allowed limited distribution of MDMA and other psychedelics such as psilocybin upon application to and approval by Health Canada.[30][31]