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]
MetabolismLiver, CYP450 extensively involved, including CYP2D6
MetabolitesMDA, HMMA, HMA, DHA, MDP2P, MDOH[14]
Onset of action30–45 minutes (by mouth)[13]
Elimination half-life(R)-MDMA: 5.8 ± 2.2 hours (variable)[15]
(S)-MDMA: 3.6 ± 0.9 hours (variable)[15]
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-Methyl​enedioxy​methamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form),[16][17] is an empathogen–entactogenic drug with stimulant and minor psychedelic properties.[18] In studies, it has been used alongside psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder.[19][20][21] The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure.[18][22] When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.[13][23]

MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch.[24] It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s.[22][23] MDMA is commonly associated with dance parties, raves, and electronic dance music.[25] Tablets sold as ecstasy may be mixed with other substances such as ephedrine, amphetamine, and methamphetamine.[22] In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population).[26] This was broadly similar to the percentage of people who use cocaine or amphetamines, but lower than for cannabis or opioids.[26] 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.[27] 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.[28]

Short-term adverse effects include grinding of the teeth, blurred vision, sweating, and a rapid heartbeat,[22] 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.[22][29] MDMA acts primarily by increasing the release of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain.[22][23] It belongs to the substituted amphetamine classes of drugs.[10][30] MDMA is structurally similar to mescaline (a psychedelic), methamphetamine (a stimulant), as well as endogenous monoamine neurotransmitters such as serotonin, norepinephrine, and dopamine.[31]

MDMA has limited approved medical uses in a small number of countries,[32] but is illegal in most jurisdictions.[33] In the United States, the Food and Drug Administration (FDA) is evaluating the drug for clinical use as of 2021.[34] Canada has allowed limited distribution of MDMA upon application to and approval by Health Canada.[35][36] In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.[37]

  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.
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  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.
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  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.
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  15. ^ a b "3,4-Methylenedioxymethamphetamine". Hazardous Substances Data Bank. National Library of Medicine. 28 August 2008. Archived from the original on 4 April 2019. Retrieved 22 August 2014.
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  18. ^ 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.
  19. ^ 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.
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