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| Clinical data | |
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| Pronunciation | methylenedioxymethamphetamine: /ˌmɛθɪliːndaɪˈɒksi/ /ˌmɛθæmˈfɛtəmiːn/ |
| Other names | 3,4-MDMA; Ecstasy (E, X, XTC); Molly; Mandy[2][3] |
| AHFS/Drugs.com | MDMA |
| Dependence liability | Physical: not typical[4] Psychological: moderate |
| Addiction liability | Low–moderate[5][6][7] |
| Routes of administration | Common: by mouth[8] Uncommon: snorting,[8] inhalation (vaporization),[8] injection,[8][9] rectal |
| Drug class | empathogen–entactogen stimulant |
| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Metabolism | Liver, CYP450 extensively involved, including CYP2D6 |
| Metabolites | MDA, HMMA, HMA, DHA, MDP2P, MDOH[10] |
| Onset of action | 30–45 minutes (by mouth)[11] |
| Elimination half-life | (R)-MDMA: 5.8 ± 2.2 hours (variable)[12] (S)-MDMA: 3.6 ± 0.9 hours (variable)[12] |
| Duration of action | 4–6 hours[6][11] |
| Excretion | Kidney |
| Identifiers | |
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| Chemical and physical data | |
| Formula | C11H15NO2 |
| Molar mass | 193.246 g·mol−1 |
| 3D model (JSmol) | |
| Chirality | Racemic mixture |
| Boiling point | 105 °C (221 °F) at 0.4 mmHg (experimental) |
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3,4-Methyl
Adverse effects include addiction, memory problems, paranoia, difficulty sleeping, teeth grinding, blurred vision, sweating and a rapid heartbeat.[15] Deaths have been reported due to increased body temperature and dehydration.[15] Following use people often feel depressed and tired.[15] MDMA acts primarily by increasing the activity of the neurotransmitters serotonin, dopamine and noradrenaline in parts of the brain.[15][16] It belongs to the substituted amphetamine classes of drugs and has stimulant and hallucinogenic effects.[8][17]
MDMA is illegal in most countries[15][18] and, as of 2018, has no approved medical uses.[8][19] Limited exceptions are sometimes made for research.[16] Researchers are investigating whether MDMA may assist in treating severe, treatment-resistant posttraumatic stress disorder (PTSD) with phase 3 clinical trials to look at effectiveness and safety expected to begin in 2018.[20] In 2017, the FDA granted MDMA a breakthrough therapy designation[note 2] for PTSD, meaning that if studies show promise, a review for potential medical use could occur more quickly.[24]
MDMA was first developed in 1912 by Merck.[25] It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s.[15][16] MDMA is commonly associated with dance parties, raves, and electronic dance music.[26] It may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine.[15] In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population).[27] This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids.[27] 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.[28]
References
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