Psychoactive drug, often called ecstasy
MDMAINN : Midomafetamine[1] Pronunciation methylenedioxymethamphetamine: Other names 3,4-MDMA ; Ecstasy (E, X, XTC); midomafetamine; Molly; Mandy;[2] [3] Pingers/Pingas[4] AHFS /Drugs.com MDMA Dependence liability Physical : not typical[5] Psychological : low–moderateAddiction 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 ATC code Legal status
Bioavailability Oral : Unknown[12] Metabolism Liver , CYP450 extensively involved, including CYP2D6 Metabolites MDA , HMMA , HMA , DHA , MDP2P , MDOH [13] Onset of action 30–45 minutes (by mouth)[12] Elimination half-life (R )-MDMA: 5.8 ± 2.2 hours (variable)[14] (S )-MDMA: 3.6 ± 0.9 hours (variable)[14] Duration of action 4–6 hours[7] [12] Excretion Kidney
(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 ) Formula C 11 H 15 N O 2 Molar mass 193.246 g·mol−1 3D model (JSmol ) Chirality Racemic mixture Density 1.1 g/cm3 Boiling point 105 °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
Y Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N
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(verify)
3,4-Methyl enedioxy methamphetamine (MDMA ), commonly known as ecstasy (tablet form), and molly or mandy (crystal form),[15] [16] is a potent empathogen–entactogen with stimulant and minor psychedelic properties.[17] Investigational indications include as an adjunct to psychotherapy in the treatment of post-traumatic stress disorder (PTSD) and social anxiety in autism spectrum disorder.[18] [19] [20] The purported pharmacological effects that may be prosocial include altered sensations, increased energy, empathy, and pleasure.[17] [21] When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.[12] [22]
MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch .[23] It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s.[21] [22] MDMA is commonly associated with dance parties , raves , and electronic dance music .[24] Tablets sold as ecstasy may be mixed with other substances such as ephedrine , amphetamine , and methamphetamine .[21] In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population).[25] This was broadly similar to the percentage of people who use cocaine or amphetamines , but lower than for cannabis or opioids .[25] 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.[26] 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.[27]
Short-term adverse effects include grinding of the teeth , blurred vision , sweating and a rapid heartbeat ,[21] 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.[21] [28] MDMA acts primarily by increasing the release of the neurotransmitters serotonin , dopamine and noradrenaline in parts of the brain.[21] [22] It belongs to the substituted amphetamine classes of drugs .[9] [29] MDMA is structurally similar to mescaline (a psychedelic), methamphetamine (a stimulant), as well as endogenous monoamine neurotransmitters such as serotonin , norepinephrine , and dopamine .[30]
MDMA has limited approved medical uses in a small number of countries,[31] but is illegal in most jurisdictions.[32] In the United States, the Food and Drug Administration is evaluating the drug for clinical use as of 2021[update] .[33] Canada has allowed limited distribution of MDMA upon application to and approval by Health Canada .[34] [35] In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.[36]
^ "FDA Substance Registration System" . United States National Library of Medicine. Archived from the original on 31 August 2017. Retrieved 31 August 2017 .
^ 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 .
^ "DrugFacts: MDMA (Ecstasy or Molly)" . National Institute on Drug Abuse. Archived from the original on 3 December 2014. Retrieved 2 December 2014 .
^ "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.
^ 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 .
^ 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 .
^ 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.
^ 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.
^ 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 .
^ "Methylenedioxymethamphetamine (MDMA, ecstasy)" . Drugs and Human Performance Fact Sheets . National Highway Traffic Safety Administration . Archived from the original on 3 May 2012.
^ 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 .
^ 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 .
^ 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. doi :10.1007/s00204-012-0815-5 . PMID 22392347 . S2CID 2873101 .
^ 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 .
^ 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 .
^ Håvard Atle Skaug, ed. (14 December 2020). "Hva er tryggest av molly og 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.
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ a b c d e f Anderson L, ed. (18 May 2014). "MDMA" . Drugs.com . Drugsite Trust. Archived from the original on 23 March 2016. Retrieved 30 March 2016 .
^ 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 .
^ 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 . Archived (PDF) from the original on 22 September 2020. Retrieved 23 May 2019 . 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.
^ 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.
^ a b World Drug Report 2018 (PDF) . United Nations. June 2018. p. 7. ISBN 978-92-1-148304-8 . Archived (PDF) from the original on 27 July 2018. Retrieved 14 July 2018 .
^ "MDMA (Ecstasy/Molly)" . National Institute on Drug Abuse . Archived from the original on 15 July 2018. Retrieved 14 July 2018 .
^ 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 .
^ 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 .
^ 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 . Archived from the original on 13 January 2023. Retrieved 12 May 2020 .
^ Lyles J, Cadet JL (May 2003). "Methylenedioxymethamphetamine (MDMA, Ecstasy) neurotoxicity: cellular and molecular mechanisms". Brain Research. Brain Research Reviews . 42 (2): 155–168. doi :10.1016/S0165-0173(03)00173-5 . PMID 12738056 . S2CID 45330713 .
^ 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 .
^ 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.
^ Nuwer R (3 May 2021). "A Psychedelic Drug Passes a Big Test for PTSD Treatment" . The New York Times . Archived from the original on 5 June 2021. Retrieved 5 June 2021 .
^ "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 .
^ "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 .
^ "Change to classification of psilocybin and MDMA to enable prescribing by authorised psychiatrists" . 3 February 2023. Archived from the original on 4 February 2024. Retrieved 4 February 2024 .