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MDMA

For other uses, see MDMA (disambiguation). Not to be confused with MDA (drug); EDMA; NMDA; or 2,3-MDMA.

MDMA
INN: Midomafetamine[1]
MDMA structure
Ball-and-stick model of an MDMA molecule
Clinical data
Pronunciationmethylenedioxy­methamphetamine:
/ˌmɛθɪliːndaɪˈɒksi/
/ˌmɛθæmˈfɛtəmiːn/
Other names3,4-MDMA; Ecstasy (E, X, XTC); Midomafetamine; Molly; Mandy;[2][3] Pingers/Pingas[4]
AHFS/Drugs.comMDMA
Dependence
liability		Physical: Not typical[5]
Psychological: Moderate[6]
Addiction
liability		Low–moderate[7][8][9]
Routes of
administration		Common: By mouth[10]
Uncommon: Insufflation,[10] inhalation,[10] injection,[10][11] rectal
Drug classEmpathogen–entactogen; Stimulant
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
BioavailabilityOral: Unknown[13]
Protein bindingUnknown[14]
MetabolismLiver, CYP450 extensively involved, including CYP2D6
MetabolitesMDA, HMMA, HMA, HHMA, HHA, THMA, THA, MDP2P, MDOH[15]
Onset of actionOral: 30–45 min[13]
Elimination half-life
  • MDMA: 8.7 (range 4.6–16) hours[16][17]
  • (S)-MDMA: 5.1 (range 3.5–7.4) hours[16]
  • (R)-MDMA: 11 (range 5.1–24) hours[16]
Duration of action4–6 hours[8][13]
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 checkY
  • Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N checkY
  (verify)

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form),[18][19] is an empathogen–entactogenic drug with stimulant and minor psychedelic properties.[17][20][21] In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder.[22][23][24] The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure.[21][25] When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.[13][26]

MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch.[27] It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s.[25][26] MDMA is commonly associated with dance parties, raves, and electronic dance music.[28] Tablets sold as ecstasy may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine.[25] In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population).[29] This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids.[29] 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.[30] 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.[31]

Short-term adverse effects include grinding of the teeth, blurred vision, sweating, and a rapid heartbeat,[25] 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.[25][32] MDMA acts primarily by increasing the release of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain.[25][26] It belongs to the substituted amphetamine classes of drugs.[10][33] MDMA is structurally similar to mescaline (a psychedelic), methamphetamine (a stimulant), as well as endogenous monoamine neurotransmitters such as serotonin, norepinephrine, and dopamine.[34]

MDMA has limited approved medical uses in a small number of countries,[35] but is illegal in most jurisdictions.[36] In the United States, the Food and Drug Administration (FDA) is evaluating the drug for clinical use as of 2021.[37] Canada has allowed limited distribution of MDMA upon application to and approval by Health Canada.[38][39] In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.[40]

  1. ^ "FDA Substance Registration System". United States National Library of Medicine. Archived from the original on 31 August 2017. 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. ISSN 1759-5061. 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 15 January 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. Archived from the original on 13 January 2023. Retrieved 4 September 2017.
  6. ^ Upfal J (2022). Australian Drug Guide: The Plain Language Guide to Drugs and Medicines of All Kinds (9th ed.). Melbourne: Black Inc. p. 319. ISBN 9781760643195. Habit-forming potential moderate. Ecstasy may induce psychological dependence and tolerance to its effect when used frequently.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ a b c d e "Methylenedioxymethamphetamine (MDMA or 'Ecstasy')". EMCDDA. European Monitoring Centre for Drugs and Drug Addiction. Archived from the original on 1 January 2016. Retrieved 17 October 2014.
  11. ^ "Methylenedioxymethamphetamine (MDMA, ecstasy)". Drugs and Human Performance Fact Sheets. National Highway Traffic Safety Administration. Archived from the original on 3 May 2012.
  12. ^ Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  13. ^ a b c d 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.
  14. ^ "Midomafetamine: Uses, Interactions, Mechanism of Action". DrugBank Online. 31 July 2007. Retrieved 11 December 2024.
  15. ^ Carvalho M, Carmo H, Costa VM, Capela JP, Pontes H, Remião F, et al. (August 2012). "Toxicity of amphetamines: an update". Archives of Toxicology. 86 (8): 1167–231. Bibcode:2012ArTox..86.1167C. doi:10.1007/s00204-012-0815-5. PMID 22392347. S2CID 2873101.
  16. ^ a b c Straumann I, Avedisian I, Klaiber A, Varghese N, Eckert A, Rudin D, et al. (August 2024). "Acute effects of R-MDMA, S-MDMA, and racemic MDMA in a randomized double-blind cross-over trial in healthy participants". Neuropsychopharmacology. 50 (2): 362–371. doi:10.1038/s41386-024-01972-6. PMC 11631982. PMID 39179638.{{cite journal}}: CS1 maint: overridden setting (link)
  17. ^ a b Dunlap LE, Andrews AM, Olson DE (October 2018). "Dark Classics in Chemical Neuroscience: 3,4-Methylenedioxymethamphetamine" (PDF). ACS Chem Neurosci. 9 (10): 2408–2427. doi:10.1021/acschemneuro.8b00155. PMC 6197894. PMID 30001118.
  18. ^ Palamar JJ (7 December 2016). "There's something about Molly: The underresearched yet popular powder form of ecstasy in the United States". Substance Abuse. 38 (1): 15–17. doi:10.1080/08897077.2016.1267070. PMC 5578728. PMID 27925866.
  19. ^ Skaug HA, ed. (14 December 2020). "Hva er tryggest av molly og ecstasy?" [What is safer: molly or ecstasy?]. Ung.no (in Norwegian). Norwegian Directorate for Children, Youth and Family Affairs. Archived from the original on 11 August 2022. Retrieved 20 June 2022. MDMA er virkestoffet i både Molly-krystaller og Ecstasy-tabletter. (MDMA is the active substance in both Molly crystals and Ecstasy tablets)
  20. ^ Green AR, Mechan AO, Elliott JM, O'Shea E, Colado MI (September 2003). "The pharmacology and clinical pharmacology of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy")". Pharmacol Rev. 55 (3): 463–508. doi:10.1124/pr.55.3.3. PMID 12869661.
  21. ^ 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.
  22. ^ Mitchell JM, Bogenschutz M, Lilienstein A, Harrison C, Kleiman S, Parker-Guilbert K, et al. (July 2023). "MDMA-Assisted Therapy for Severe PTSD: A Randomized, Double-Blind, Placebo-Controlled Phase 3 Study". Focus. 21 (3): 315–328. doi:10.1176/appi.focus.23021011. PMC 10316215. PMID 37404971.
  23. ^ Danforth AL, Struble CM, Yazar-Klosinski B, Grob CS (January 2016). "MDMA-assisted therapy: A new treatment model for social anxiety in autistic adults". Progress in Neuro-Psychopharmacology & Biological Psychiatry. 64: 237–249. doi:10.1016/j.pnpbp.2015.03.011. PMID 25818246.
  24. ^ Danforth AL, Grob CS, Struble C, Feduccia AA, Walker N, Jerome L, et al. (November 2018). "Reduction in social anxiety after MDMA-assisted psychotherapy with autistic adults: a randomized, double-blind, placebo-controlled pilot study". Psychopharmacology. 235 (11): 3137–3148. doi:10.1007/s00213-018-5010-9. PMC 6208958. PMID 30196397.
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  28. ^ 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.
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  31. ^ White CM (March 2014). "How MDMA's pharmacology and pharmacokinetics drive desired effects and harms". Journal of Clinical Pharmacology. 54 (3): 245–252. doi:10.1002/jcph.266. PMID 24431106. S2CID 6223741.
  32. ^ Sessa B, Aday JS, O'Brien S, Curran HV, Measham F, Higbed L, et al. (March 2022). "Debunking the myth of 'Blue Mondays': No evidence of affect drop after taking clinical MDMA". Journal of Psychopharmacology. 36 (3): 360–367. doi:10.1177/02698811211055809. PMID 34894842. S2CID 245184699.
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  38. ^ "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". Health Canada. 5 January 2022. Archived from the original on 11 February 2022. Retrieved 20 February 2022.
  39. ^ "Canada approving psychedelics for therapy is a positive step, experts say - National". Globalnews.ca. Archived from the original on 20 February 2022. Retrieved 20 February 2022.
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MDMA

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