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MDMA information

INN: Midomafetamine[1]
MDMA structure
Ball-and-stick model of an MDMA molecule
Clinical data
Other names3,4-MDMA; Ecstasy (E, X, XTC); Molly; Mandy;[2][3] Pingers/Pingas[4]
Physical: not typical[5]
Psychological: moderate
Routes of
Common: by mouth[9]
Uncommon: snorting,[9] inhalation (vaporization),[9] injection,[9][10] rectal
Drug classEmpathogen–entactogen
ATC code
  • None
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F (Prohibited substances)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • NZ: Class B
  • UK: Class A
  • US: Schedule I
  • UN: Psychotropic Schedule I
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]
IUPAC name
  • (RS)-1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine
CAS Number
  • 42542-10-9 checkY[TOXNET]
PubChem CID
  • 1615
  • 4574
  • DB01454 checkY
  • 1556 checkY
  • KE1SEN21RM
  • D11172 checkY
  • CHEBI:1391 checkY
  • ChEMBL43048 checkY
PDB ligand
  • B41 (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID90860791 Edit this at Wikidata
Chemical and physical data
Molar mass193.246 g·mol−1
3D model (JSmol)
  • Interactive image
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 checkY

3,4-Methyl​enedioxy​methamphetamine (MDMA), commonly known as ecstasy (tablet form); and molly or mandy (crystal form),[14][15] is a potent empathogen–entactogen with stimulant properties 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 three to six hours.[12][18]

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, although this effect does not appear in clinical use, suggesting that it is not a direct result of MDMA administration.[17] [23] 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.[9][24]

MDMA is illegal in most countries[17][25] and has limited approved medical uses in a small number of countries.[9][26] In the United States, the Food and Drug Administration is currently evaluating the drug for clinical use.[27] Canada has allowed limited distribution of MDMA and other psychedelics such as psilocybin upon application to and approval by Health Canada.[28][29]

  1. ^ "FDA Substance Registration System". United States National Library of Medicine. Retrieved 31 August 2017.
  2. ^ Luciano RL, Perazella MA (June 2014). "Nephrotoxic effects of designer drugs: synthetic is not better!". Nature Reviews. Nephrology. 10 (6): 314–24. doi:10.1038/nrneph.2014.44. PMID 24662435. S2CID 9817771.
  3. ^ "DrugFacts: MDMA (Ecstasy or Molly)". National Institute on Drug Abuse. Archived from the original on 3 December 2014. Retrieved 2 December 2014.
  4. ^ "Pingers, pingas, pingaz: how drug slang affects the way we use and understand drugs". The Conversation. 8 January 2020. Archived from the original on 2021.
  5. ^ Palmer RB (2012). Medical toxicology of drug abuse : synthesized chemicals and psychoactive plants. Hoboken, N.J.: John Wiley & Sons. p. 139. ISBN 978-0-471-72760-6.
  6. ^ Malenka RC, Nestler EJ, Hyman SE (2009). "Chapter 15: Reinforcement and Addictive Disorders". In Sydor A, Brown RY (eds.). Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2nd ed.). New York: McGraw-Hill Medical. p. 375. ISBN 978-0-07-148127-4.
  7. ^ a b Betzler F, Viohl L, Romanczuk-Seiferth N (January 2017). "Decision-making in chronic ecstasy users: a systematic review". The European Journal of Neuroscience. 45 (1): 34–44. doi:10.1111/ejn.13480. PMID 27859780. S2CID 31694072. ...the addictive potential of MDMA itself is relatively small.
  8. ^ Jerome L, Schuster S, Yazar-Klosinski BB (March 2013). "Can MDMA play a role in the treatment of substance abuse?" (PDF). Current Drug Abuse Reviews. 6 (1): 54–62. doi:10.2174/18744737112059990005. PMID 23627786. S2CID 9327169. Archived from the original (PDF) on 3 August 2020. Animal and human studies demonstrate moderate abuse liability for MDMA, and this effect may be of most concern to those treating substance abuse disorders.
  9. ^ a b c d e f "Methylenedioxymethamphetamine (MDMA or 'Ecstasy')". EMCDDA. European Monitoring Centre for Drugs and Drug Addiction. Retrieved 17 October 2014.
  10. ^ "Methylenedioxymethamphetamine (MDMA, ecstasy)". Drugs and Human Performance Fact Sheets. National Highway Traffic Safety Administration. Archived from the original on 3 May 2012.
  11. ^ Carvalho M, Carmo H, Costa VM, Capela JP, Pontes H, Remião F, Carvalho F, Bastos M (August 2012). "Toxicity of amphetamines: an update". Archives of Toxicology. 86 (8): 1167–231. doi:10.1007/s00204-012-0815-5. PMID 22392347. S2CID 2873101.
  12. ^ a b c Freye E (28 July 2009). "Pharmacological Effects of MDMA in Man". Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs. Springer Netherlands. pp. 151–160. doi:10.1007/978-90-481-2448-0_24. ISBN 978-90-481-2448-0.
  13. ^ a b "3,4-Methylenedioxymethamphetamine". Hazardous Substances Data Bank. National Library of Medicine. 28 August 2008. Retrieved 22 August 2014.
  14. ^ Palamar JJ (7 December 2016). "There's Something About Molly: The Under-Researched yet Popular Powder Form of Ecstasy in the United States". The Center for Drug Use and HIV Research. 38, 1 (Substance abuse): 15–17. doi:10.1080/08897077.2016.1267070. PMC 5578728. PMID 27925866.
  15. ^ Håvard Atle Skaug, ed. (14 December 2020). "Hva er tryggest av molly og ecstasy?". (in Norwegian). Norwegian Directorate for Children, Youth and Family Affairs. Retrieved 20 June 2022. MDMA er virkestoffet i både Molly-krystaller og Ecstasy-tabletter.
  16. ^ a b Meyer JS (2013). "3,4-methylenedioxymethamphetamine (MDMA): current perspectives". Substance Abuse and Rehabilitation. 4: 83–99. doi:10.2147/SAR.S37258. PMC 3931692. PMID 24648791.
  17. ^ a b c d e f g Anderson L, ed. (18 May 2014). "MDMA". Drugsite Trust. Archived from the original on 23 March 2016. Retrieved 30 March 2016.
  18. ^ a b c "DrugFacts: MDMA (Ecstasy/Molly)". National Institute on Drug Abuse. February 2016. Archived from the original on 23 March 2016. Retrieved 30 March 2016.
  19. ^ Freudenmann RW, Öxler F, Bernschneider-Reif S (August 2006). "The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents" (PDF). Addiction. 101 (9): 1241–1245. doi:10.1111/j.1360-0443.2006.01511.x. PMID 16911722. Although MDMA was, in fact, first synthesized at Merck in 1912, it was not tested pharmacologically because it was only an unimportant precursor in a new synthesis for haemostatic substances.
  20. ^ World Health Organization (2004). Neuroscience of Psychoactive Substance Use and Dependence. World Health Organization. pp. 97–. ISBN 978-92-4-156235-5. Archived from the original on 28 April 2016.
  21. ^ a b World Drug Report 2018 (PDF). United Nations. June 2018. p. 7. ISBN 978-92-1-148304-8. Retrieved 14 July 2018.
  22. ^ "MDMA (Ecstasy/Molly)". National Institute on Drug Abuse. Retrieved 14 July 2018.
  23. ^ Sessa, Ben (2022). "Dr". Journal of Psychopharmacology. 36 (3): 360–367. doi:10.1177/02698811211055809. PMID 34894842. S2CID 245184699.
  24. ^ Freye E (2009). Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs: A comprehensive review on their mode of action, treatment of abuse and intoxication. Springer Science & Business Media. p. 147. ISBN 978-90-481-2448-0.
  25. ^ Patel V (2010). Mental and neurological public health a global perspective (1st ed.). San Diego, CA: Academic Press/Elsevier. p. 57. ISBN 978-0-12-381527-9. Archived from the original on 10 September 2017.
  26. ^ Philipps D (1 May 2018). "Ecstasy as a Remedy for PTSD? You Probably Have Some Questions". The New York Times. Archived from the original on 1 January 2022. Retrieved 14 July 2018.
  27. ^ Nuwer R (3 May 2021). "A Psychedelic Drug Passes a Big Test for PTSD Treatment". The New York Times.
  28. ^ Health Canada (5 January 2022). "Subsection 56(1) class exemption for practitioners, agents, pharmacists, persons in charge of a hospital, hospital employees, and licensed dealers to conduct activities with psilocybin and MDMA in relation to a special access program authorization". Retrieved 20 February 2022.
  29. ^ "Canada approving psychedelics for therapy is a positive step, experts say - National |". Global News. Retrieved 20 February 2022.

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