User:Mr. Ibrahem/MDMA

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Not to be confused with MDA, EDMA 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); Molly; Mandy[2][3]
AHFS/Drugs.comMDMA
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 classempathogen–entactogen
stimulant
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver, CYP450 extensively involved, including CYP2D6
MetabolitesMDA, HMMA, HMA, DHA, MDP2P, MDOH[10]
Onset of action30–45 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 action4–6 hours[6][11]
ExcretionKidney
Identifiers
  • (RS)-1-(1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine
Chemical and physical data
FormulaC11H15NO2
Molar mass193.246 g·mol−1
3D model (JSmol)
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
  • Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N checkY
  (verify)

3,4-Methyl​enedioxy​methamphetamine (MDMA),[note 1] commonly known as ecstasy (E) or molly, is a psychoactive drug primarily used for recreational purposes.[14] The desired effects include altered sensations, increased energy, empathy, as well as pleasure.[14][15] When taken by mouth, effects begin in 30 to 45 minutes and last 3 to 6 hours.[11][16]

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[edit]

  1. ^ "FDA Substance Registration System". United States National Library of Medicine. Archived from the original on 31 August 2017. Retrieved 31 August 2017.
  2. ^ a b 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.
  3. ^ a b "DrugFacts: MDMA (Ecstasy or Molly)". National Institute on Drug Abuse. Archived from the original on 3 December 2014. Retrieved 2 December 2014.
  4. ^ Palmer, Robert B. (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 22 December 2020. Retrieved 30 July 2020.
  5. ^ 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.
  6. ^ 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. ...the addictive potential of MDMA itself is relatively small.
  7. ^ 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. Archived from the original (PDF) on 3 August 2020. Retrieved 30 July 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.
  8. ^ a b c d e f "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.
  9. ^ "Methylenedioxymethamphetamine (MDMA, ecstasy)". Drugs and Human Performance Fact Sheets. National Highway Traffic Safety Administration. Archived from the original on 3 May 2012.
  10. ^ 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.
  11. ^ a b c Freye, Enno (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.
  12. ^ 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.
  13. ^ "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 1 July 2021. Retrieved 9 September 2020.
  14. ^ 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  15. ^ a b c d e f g h Anderson, Leigh, ed. (18 May 2014). "MDMA". Drugs.com. Drugsite Trust. Archived from the original on 23 March 2016. Retrieved 30 March 2016.
  16. ^ a b c d "DrugFacts: MDMA (Ecstasy/Molly)". National Institute on Drug Abuse. February 2016. Archived from the original on 23 March 2016. Retrieved 30 March 2016.
  17. ^ Freye, Enno (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 5 August 2020. Retrieved 30 July 2020.
  18. ^ Patel, Vikram (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.
  19. ^ Philipps, Dave (1 May 2018). "Ecstasy as a Remedy for PTSD? You Probably Have Some Questions". The New York Times. Archived from the original on 15 July 2018. Retrieved 14 July 2018.
  20. ^ Feduccia AA, Holland J, Mithoefer MC (February 2018). "Progress and promise for the MDMA drug development program". Psychopharmacology. 235 (2): 561–571. doi:10.1007/s00213-017-4779-2. PMID 29152674.
  21. ^ Schwitzer G (13 May 2016). "CBS proclaims 'cancer breakthrough' – doesn't explain what FDA means by that term". Health News Review. Archived from the original on 8 December 2020. Retrieved 9 October 2017.
  22. ^ a b Kepplinger EE (February 2015). "FDA's Expedited Approval Mechanisms for New Drug Products". Biotechnology Law Report. 34 (1): 15–37. doi:10.1089/blr.2015.9999. PMC 4326266. PMID 25713472.
  23. ^ "Fact Sheet: Breakthrough Therapies". United States Food and Drug Administration. 10 December 2014. Archived from the original on 9 October 2017. Retrieved 9 October 2017. A breakthrough therapy is a drug:
     • intended alone or in combination with one or more other drugs to treat a serious or life-threatening disease or condition and
     • preliminary clinical evidence indicates that the drug may demonstrate substantial improvement over existing therapies on one or more clinically significant endpoints, such as substantial treatment effects observed early in clinical development.
  24. ^ Wan, William (26 August 2017). "Ecstasy could be 'breakthrough' therapy for soldiers, others suffering from PTSD". Washington Post. Archived from the original on 29 August 2017. Retrieved 29 August 2017.
  25. ^ 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 30 July 2020. 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.
  26. ^ 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.
  27. ^ 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.
  28. ^ "MDMA (Ecstasy/Molly)". National Institute on Drug Abuse. Archived from the original on 15 July 2018. Retrieved 14 July 2018.


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