Editing MDMA (section)

{{Short description|Psychoactive drug, often called ecstasy}}
{{Hatnote group|
{{Other uses}}
{{Distinguish|MDA (drug)|EDMA|NMDA|2,3-MDMA}}
}}
{{pp-vandalism|small=yes}}
<!-- Definition and uses -->
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Use dmy dates|date=August 2017}}
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 632164040
| drug_name = MDMA
| INN = Midomafetamine<ref name=INN>{{cite news|title=FDA Substance Registration System|url=https://fdasis.nlm.nih.gov/srs/unii/KE1SEN21RM|access-date=31 August 2017|publisher=[[United States National Library of Medicine]]|archive-date=31 August 2017|archive-url=https://web.archive.org/web/20170831220013/https://fdasis.nlm.nih.gov/srs/unii/KE1SEN21RM|url-status=dead}}</ref>
| image = Midomafetamine enantiomers labelled.svg
| image_class = skin-invert-image
| width = 250px
| alt = MDMA structure
| image2 = MDMA-enantiomers-3D-balls.png
| alt2 = Ball-and-stick model of MDMA molecule enantiomers
| width2 = 250px
| caption = Skeletal structures of (''R'')-MDMA (top) and (''S'')-MDMA (bottom)
| caption2 = Ball-and-stick models of (''R'')-MDMA (top) and (''S'')-MDMA (bottom)

<!-- Clinical data -->
| pronounce = methylenedioxy{{shy}}methamphetamine:<br />{{IPAc-en|ˌ|m|ɛ|θ|ᵻ|l|iː|n|d|aɪ|ˈ|ɒ|k|s|i}}<br />{{IPAc-en|ˌ|m|ɛ|θ|æ|m|ˈ|f|ɛ|t|əm|iː|n}}
| pregnancy_category = 
| pregnancy_US = 
| licence_US = 
| class = [[Entactogen]]; [[Stimulant]]; [[Serotonergic psychedelic|Psychedelic]]; [[Serotonin–norepinephrine–dopamine releasing agent]]; [[Serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]] [[agonist]]
| routes_of_administration = Common: [[oral route|By mouth]]<ref name=EU2015 /><br /> Uncommon: [[Insufflation]],<ref name=EU2015 /> [[inhalation]],<ref name=EU2015 /> [[injection (medicine)|injection]],<ref name=EU2015>{{cite web|title=Methylenedioxymethamphetamine (MDMA or 'Ecstasy')|url=http://www.emcdda.europa.eu/publications/drug-profiles/mdma|website=EMCDDA|publisher=European Monitoring Centre for Drugs and Drug Addiction|access-date=17 October 2014|ref=EMCDDA|archive-date=1 January 2016|archive-url=https://web.archive.org/web/20160101211851/http://www.emcdda.europa.eu/publications/drug-profiles/mdma|url-status=live}}</ref><ref>{{cite web|title = Methylenedioxymethamphetamine (MDMA, ecstasy)|url = http://www.nhtsa.dot.gov/people/injury/research/job185drugs/methylenedioxymethamphetamine.htm|work = Drugs and Human Performance Fact Sheets.|publisher = [[National Highway Traffic Safety Administration]]|url-status=dead|archive-url = https://web.archive.org/web/20120503102427/http://www.nhtsa.gov/people/injury/research/job185drugs/methylenedioxymethamphetamine.htm|archive-date = 3 May 2012|df = dmy-all}}</ref> [[rectal (medicine)|rectal]]
| dependency_liability = [[Physical dependence|Physical]]: Not typical<ref name=palmer>{{cite book|vauthors=Palmer RB|title=Medical toxicology of drug abuse : synthesized chemicals and psychoactive plants|date=2012|publisher=John Wiley & Sons|location=Hoboken, N.J.|isbn=978-0-471-72760-6|page=139|url=https://books.google.com/books?id=OWFiVaDZnkQC&pg=PA139|access-date=4 September 2017|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113000533/https://books.google.com/books?id=OWFiVaDZnkQC&pg=PA139|url-status=live}}</ref><br />[[Psychological dependence|Psychological]]: Moderate<ref>{{Cite book |title=Australian Drug Guide: The Plain Language Guide to Drugs and Medicines of All Kinds |vauthors=Upfal J |publisher=Black Inc |year=2022 |isbn=9781760643195 |edition=9th |location=Melbourne |pages=319 |quote=Habit-forming potential moderate. Ecstasy may induce psychological dependence and tolerance to its effect when used frequently.}}</ref>
| addiction_liability = Low–moderate<ref name="NHM-MDMA">{{cite book |vauthors=Malenka RC, Nestler EJ, Hyman SE |veditors=Sydor A, Brown RY | title = Molecular Neuropharmacology: A Foundation for Clinical Neuroscience | year = 2009 | publisher = McGraw-Hill Medical | location = New York | isbn = 978-0-07-148127-4 | pages = 375 | edition = 2nd | chapter = Chapter 15: Reinforcement and Addictive Disorders}}</ref><ref name=Betzler2017>{{cite journal | vauthors = Betzler F, Viohl L, Romanczuk-Seiferth N | title = Decision-making in chronic ecstasy users: a systematic review | journal = The European Journal of Neuroscience | volume = 45 | issue = 1 | pages = 34–44 | date = January 2017 | pmid = 27859780 | doi = 10.1111/ejn.13480 | s2cid = 31694072 | quote = ...the addictive potential of MDMA itself is relatively small.| doi-access = free }}</ref><ref name="Substance abuse">{{cite journal | vauthors = Jerome L, Schuster S, Yazar-Klosinski BB | title = Can MDMA play a role in the treatment of substance abuse? | journal = Current Drug Abuse Reviews | volume = 6 | issue = 1 | pages = 54–62 | date = March 2013 | pmid = 23627786 | doi = 10.2174/18744737112059990005 | s2cid = 9327169 | quote = Animal and human studies demonstrate moderate abuse liability for MDMA, and this effect may be of most concern to those treating substance abuse disorders. | url = http://pdfs.semanticscholar.org/33fd/4f5decd405dee8d4f280a9158bfb16ae6e27.pdf | archive-url = https://web.archive.org/web/20200803194522/http://pdfs.semanticscholar.org/33fd/4f5decd405dee8d4f280a9158bfb16ae6e27.pdf | url-status = dead | archive-date = 2020-08-03}}</ref>

<!-- Legal status -->
| legal_AU = {{unbulleted list
|S8 (PTSD)
|S9 (all other uses)
}}
| legal_BR = F2
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>
| legal_CA = Schedule I
| legal_DE = Anlage I
| legal_NZ = Class B
| legal_UK = Class A
| legal_US = Schedule I
| legal_UN = Psychotropic Schedule I
| legal_status =

<!-- Pharmacokinetic data -->
| bioavailability = [[Oral administration|Oral]]: Unknown<ref name="Freye2009"/>
| protein_bound = Unknown<ref name="DrugBank">{{cite web | title=Midomafetamine: Uses, Interactions, Mechanism of Action | website=DrugBank Online | date=31 July 2007 | url=https://go.drugbank.com/drugs/DB01454 | access-date=11 December 2024}}</ref>
| onset = [[Oral administration|Oral]]: 30–45{{nbsp}}min<ref name=Freye2009/>
| metabolism = [[Liver]], [[Cytochrome P450 oxidase|CYP450]] extensively involved, including [[CYP2D6]]
| metabolites = [[3,4-methylenedioxyamphetamine|MDA]], [[4-Hydroxy-3-methoxymethamphetamine|HMMA]], [[4-Hydroxy-3-methoxyamphetamine|HMA]], [[3,4-Dihydroxymethamphetamine|HHMA]], [[Alpha-Methyldopamine|HHA]], [[2,4,5-Trihydroxymethamphetamine|THMA]], [[2,4,5-Trihydroxyamphetamine|THA]], [[MDP2P]], [[Methylenedioxyhydroxyamphetamine|MDOH]]<ref name="pmid22392347">{{cite journal | vauthors = Carvalho M, Carmo H, Costa VM, Capela JP, Pontes H, Remião F, Carvalho F, Bastos M | title = Toxicity of amphetamines: an update | journal = Archives of Toxicology | volume = 86 | issue = 8 | pages = 1167–231 | date = August 2012 | pmid = 22392347 | doi = 10.1007/s00204-012-0815-5 | bibcode = 2012ArTox..86.1167C | s2cid = 2873101}}</ref>
| elimination_half-life = {{Bulleted list | MDMA: 8.7 (range 4.6–16) hours<ref name="StraumannAvedisianKlaiber2024" /><ref name="DunlapAndrewsOlson2018" /> | (''S'')-MDMA: 5.1 (range 3.5–7.4) hours<ref name="StraumannAvedisianKlaiber2024">{{cite journal | vauthors = Straumann I, Avedisian I, Klaiber A, Varghese N, Eckert A, Rudin D, Luethi D, Liechti ME | title = Acute effects of R-MDMA, S-MDMA, and racemic MDMA in a randomized double-blind cross-over trial in healthy participants | journal = Neuropsychopharmacology | volume = 50| issue = 2| date = August 2024 | pages = 362–371 | pmid = 39179638 | doi = 10.1038/s41386-024-01972-6 | doi-access = free | pmc = 11631982 }}</ref> | [[(R)-MDMA|(''R'')-MDMA]]: 11 (range 5.1–24) hours<ref name="StraumannAvedisianKlaiber2024" />}}
| duration_of_action = 3–6{{nbsp}}hours<ref name="Oeri2021" /><ref name="Betzler2017" /><ref name="Freye2009" />
| excretion = [[Kidney]]

<!-- Identifiers -->
| ATC_prefix = None
| Drugs.com = {{Drugs.com|parent|MDMA}}
| CAS_number_Ref = {{cascite|correct|TOXNET}}
| CAS_number = 42542-10-9
|CAS_supplemental=<br/>{{CAS|64057-70-1}} [[Hydrochloride|(HCl)]]
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 1556
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KE1SEN21RM
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01454
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 1391
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 43048
| PubChem = 1615
| IUPHAR_ligand = 4574
| KEGG = D11172
| KEGG_Ref = {{keggcite|correct|kegg}}
| PDB_ligand = B41
| synonyms = {{abbr|3,4-MDMA|3,4-Methylenedioxymethamphetamine}}; Ecstasy (E, X, XTC); Midomafetamine; Molly; Mandy;<ref name="nature.com">{{cite journal | vauthors = Luciano RL, Perazella MA | title = Nephrotoxic effects of designer drugs: synthetic is not better! | journal = Nature Reviews. Nephrology | volume = 10 | issue = 6 | pages = 314–24 | date = June 2014 | pmid = 24662435 | doi = 10.1038/nrneph.2014.44 | s2cid = 9817771|issn=1759-5061}}</ref><ref name="DrugFacts">{{cite web|title=DrugFacts: MDMA (Ecstasy or Molly)|url=http://www.drugabuse.gov/publications/drugfacts/mdma-ecstasy-or-molly|publisher=National Institute on Drug Abuse|access-date=2 December 2014|url-status=dead|archive-url=https://web.archive.org/web/20141203115531/http://www.drugabuse.gov/publications/drugfacts/mdma-ecstasy-or-molly|archive-date=3 December 2014|df=dmy-all}}</ref> Pingers/Pingas<ref>{{cite web|url=https://theconversation.com/pingers-pingas-pingaz-how-drug-slang-affects-the-way-we-use-and-understand-drugs-129452|title=Pingers, pingas, pingaz: how drug slang affects the way we use and understand drugs|publisher=[[The Conversation (website)|The Conversation]]|date=2020-01-08|archive-url=https://web.archive.org/web/20210115205246/https://theconversation.com/pingers-pingas-pingaz-how-drug-slang-affects-the-way-we-use-and-understand-drugs-129452|archive-date=2021-01-15|url-status=live}}</ref>

<!-- Chemical data -->
| IUPAC_name = (''RS'')-1-(1,3-Benzodioxol-5-yl)-''N''-methylpropan-2-amine<!--From PubChem-->
| C=11 | H=15 | N=1 | O=2
| chirality = [[Racemic mixture]]
| SMILES = CC(NC)CC1=CC=C(OCO2)C2=C1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SHXWCVYOXRDMCX-UHFFFAOYSA-N

<!-- Physical data -->
| density = 1.1
| melting_point = 
| melting_notes = 
| boiling_point = 105
| boiling_notes = at 0.4{{nbsp}}mmHg (experimental)<!--Pubchem-->
}}

'''3,4-Methylenedioxymethamphetamine''' ('''MDMA'''), commonly known as '''ecstasy''' (tablet form), and '''molly''' (crystal form),<ref>{{cite journal | vauthors = Palamar JJ | title = There's something about Molly: The underresearched yet popular powder form of ecstasy in the United States | journal = Substance Abuse | volume = 38 | issue = 1 | pages = 15–17 | date = 2016-12-07 | pmid = 27925866 | pmc = 5578728 | doi = 10.1080/08897077.2016.1267070 }}</ref><ref>{{Cite web | veditors = Skaug HA |title=Hva er tryggest av molly og ecstasy? | trans-title = What is safer: molly or ecstasy? |url=https://www.ung.no/oss/rusmidler/462397.html |access-date=2022-06-20 |publisher=Norwegian Directorate for Children, Youth and Family Affairs |website=Ung.no |language=no |publication-date=2020-12-14 |quote=MDMA er virkestoffet i både Molly-krystaller og Ecstasy-tabletter. (MDMA is the active substance in both Molly crystals and Ecstasy tablets) |archive-date=11 August 2022 |archive-url=https://web.archive.org/web/20220811145918/https://www.ung.no/oss/rusmidler/462397.html |url-status=live }}</ref> is an [[empathogen–entactogen]]ic drug with [[stimulant]] and minor [[Psychedelic drug|psychedelic]] properties.<ref name="DunlapAndrewsOlson2018">{{cite journal | vauthors = Dunlap LE, Andrews AM, Olson DE | title = Dark Classics in Chemical Neuroscience: 3,4-Methylenedioxymethamphetamine | journal = ACS Chem Neurosci | volume = 9 | issue = 10 | pages = 2408–2427 | date = October 2018 | pmid = 30001118 | pmc = 6197894 | doi = 10.1021/acschemneuro.8b00155 | url = https://shaunlacob.com/wp-content/uploads/2020/12/DC-MDMA.pdf}}</ref><ref name="GreenMechanElliott2003">{{cite journal | vauthors = Green AR, Mechan AO, Elliott JM, O'Shea E, Colado MI | title = The pharmacology and clinical pharmacology of 3,4-methylenedioxymethamphetamine (MDMA, "ecstasy") | journal = Pharmacol Rev | volume = 55 | issue = 3 | pages = 463–508 | date = September 2003 | pmid = 12869661 | doi = 10.1124/pr.55.3.3 | url = }}</ref><ref name="Current2013">{{cite journal | vauthors = Meyer JS | title = 3,4-methylenedioxymethamphetamine (MDMA): current perspectives | journal = Substance Abuse and Rehabilitation | volume = 4 | pages = 83–99 | year = 2013 | pmid = 24648791 | pmc = 3931692 | doi = 10.2147/SAR.S37258 | doi-access = free }}</ref> In studies, it has been used alongside [[psychotherapy]] in the treatment of [[post-traumatic stress disorder]] (PTSD) and [[social anxiety]] in [[Autism|autism spectrum disorder]].<ref>{{cite journal | vauthors = Mitchell JM, Bogenschutz M, Lilienstein A, Harrison C, Kleiman S, Parker-Guilbert K, Ot'alora GM, Garas W, Paleos C, Gorman I, Nicholas C, Mithoefer M, Carlin S, Poulter B, Mithoefer A, Quevedo S, Wells G, Klaire SS, van der Kolk B, Tzarfaty K, Amiaz R, Worthy R, Shannon S, Woolley JD, Marta C, Gelfand Y, Hapke E, Amar S, Wallach Y, Brown R, Hamilton S, Wang JB, Coker A, Matthews R, de Boer A, Yazar-Klosinski B, Emerson A, Doblin R | title = MDMA-Assisted Therapy for Severe PTSD: A Randomized, Double-Blind, Placebo-Controlled Phase 3 Study | journal = Focus | volume = 21 | issue = 3 | pages = 315–328 | date = July 2023 | pmid = 37404971 | pmc = 10316215 | doi = 10.1176/appi.focus.23021011 }}</ref><ref name=":1">{{cite journal | vauthors = Danforth AL, Struble CM, Yazar-Klosinski B, Grob CS | title = MDMA-assisted therapy: A new treatment model for social anxiety in autistic adults | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 64 | pages = 237–249 | date = January 2016 | pmid = 25818246 | doi = 10.1016/j.pnpbp.2015.03.011 | doi-access = free }}</ref><ref name=":2">{{cite journal | vauthors = Danforth AL, Grob CS, Struble C, Feduccia AA, Walker N, Jerome L, Yazar-Klosinski B, Emerson A | title = Reduction in social anxiety after MDMA-assisted psychotherapy with autistic adults: a randomized, double-blind, placebo-controlled pilot study | journal = Psychopharmacology | volume = 235 | issue = 11 | pages = 3137–3148 | date = November 2018 | pmid = 30196397 | doi = 10.1007/s00213-018-5010-9 | pmc = 6208958 }}</ref> The purported pharmacological effects that may be [[Prosocial behavior|prosocial]] include altered sensations, increased energy, empathy, and pleasure.<ref name=Current2013/><!-- quote = desire to experience an altered state of consciousness --><ref name=Drugs2014>{{cite web |title=MDMA|url=https://www.drugs.com/illicit/mdma.html|access-date=30 March 2016| veditors=Anderson L |website=Drugs.com|publisher=Drugsite Trust|date=18 May 2014|url-status=live |archive-url=https://web.archive.org/web/20160323161153/http://www.drugs.com/illicit/mdma.html |archive-date=23 March 2016}}</ref><!-- Quote = producing an energizing effect, as well as distortions in time and perception and enhanced enjoyment from tactile experiences --> When taken by mouth, effects begin in 30 to 45 minutes and last three to six hours.<ref name=Freye2009>{{cite book| vauthors = Freye E |title=Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs|date=28 July 2009|publisher=Springer Netherlands|isbn=978-90-481-2448-0|pages=151–160|chapter=Pharmacological Effects of MDMA in Man|doi=10.1007/978-90-481-2448-0_24}}</ref><ref name=NIH2016/>

<!-- Usage and history -->
MDMA was first synthesized in 1912 by [[Merck Group|Merck]] chemist [[Anton Köllisch]].<ref name="FreudenmannÖxlerBernschneider-Reif2006">{{cite journal | vauthors = Freudenmann RW, Öxler F, Bernschneider-Reif S | title = The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents | url = http://www.thedea.org/docs/2006_Freudenmann_22846_1.pdf | journal = Addiction | volume = 101 | issue = 9 | pages = 1241–1245 | date = August 2006 | pmid = 16911722 | doi = 10.1111/j.1360-0443.2006.01511.x | quote = 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. | access-date = 23 May 2019 | archive-date = 22 September 2020 | archive-url = https://web.archive.org/web/20200922140222/http://www.thedea.org/docs/2006_Freudenmann_22846_1.pdf | url-status = live }}</ref> It was used to enhance psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s.<ref name=Drugs2014/><ref name=NIH2016/> MDMA is commonly associated with [[dance party|dance parties]], [[rave]]s, and [[electronic dance music]].<ref name=WHO2004>{{cite book|author=World Health Organization|title=Neuroscience of Psychoactive Substance Use and Dependence|url=https://books.google.com/books?id=G9OhG-dZdAwC&pg=PA97|year=2004|publisher=World Health Organization|isbn=978-92-4-156235-5|pages=97–|url-status=live|archive-url=https://web.archive.org/web/20160428231233/https://books.google.com/books?id=G9OhG-dZdAwC&pg=PA97|archive-date=28 April 2016|df=dmy-all}}</ref> Tablets sold as ecstasy may be [[Cutting agent|mixed]] with other substances such as [[ephedrine]], [[amphetamine]], and [[methamphetamine]].<ref name=Drugs2014/> In 2016, about 21 million people between the ages of 15 and 64 used ecstasy (0.3% of the world population).<ref name=UN2018>{{cite book |title=World Drug Report 2018 |date=June 2018 |publisher=United Nations |isbn=978-92-1-148304-8 |page=7 |access-date=14 July 2018 |url=https://www.unodc.org/wdr2018/prelaunch/WDR18_Booklet_1_EXSUM.pdf |archive-date=27 July 2018 |archive-url=https://web.archive.org/web/20180727030037/http://www.unodc.org/wdr2018/prelaunch/WDR18_Booklet_1_EXSUM.pdf |url-status=live }}</ref> This was broadly similar to the percentage of people who use [[cocaine]] or [[substituted amphetamine|amphetamine]]s, but lower than for [[Cannabis (drug)|cannabis]] or [[opioid]]s.<ref name=UN2018/> 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.<ref>{{cite web |title=MDMA (Ecstasy/Molly) |url=https://www.drugabuse.gov/drugs-abuse/mdma-ecstasymolly |website=National Institute on Drug Abuse |access-date=14 July 2018 |archive-date=15 July 2018 |archive-url=https://web.archive.org/web/20180715011009/https://www.drugabuse.gov/drugs-abuse/mdma-ecstasymolly |url-status=live }}</ref> 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.<ref>{{cite journal | vauthors = White CM | title = How MDMA's pharmacology and pharmacokinetics drive desired effects and harms | journal = Journal of Clinical Pharmacology | volume = 54 | issue = 3 | pages = 245–252 | date = March 2014 | pmid = 24431106 | doi = 10.1002/jcph.266 | s2cid = 6223741 }}</ref>

<!-- Side effects, chemistry and mechanism -->
Short-term adverse effects include [[Bruxism|grinding of the teeth]], [[blurred vision]], [[sweating]], and a [[Tachycardia|rapid heartbeat]],<ref name="Drugs2014" /> and extended use can also lead to addiction, [[Amnesia|memory problems]], [[paranoia]], and [[Insomnia|difficulty sleeping]]. Deaths have been reported due to increased body temperature and dehydration. Following use, people often feel [[Depression (mood)|depressed]] and tired, although this effect does not appear in clinical use, suggesting that it is not a direct result of MDMA administration.<ref name=Drugs2014/><ref>{{cite journal | vauthors = Sessa B, Aday JS, O'Brien S, Curran HV, Measham F, Higbed L, Nutt DJ | title = Debunking the myth of 'Blue Mondays': No evidence of affect drop after taking clinical MDMA | journal = Journal of Psychopharmacology | volume = 36 | issue = 3 | pages = 360–367 | date = March 2022 | pmid = 34894842 | doi = 10.1177/02698811211055809 | s2cid = 245184699 }}</ref> MDMA acts primarily by increasing the release of the [[neurotransmitters]] [[serotonin]], [[dopamine]], and [[norepinephrine]] in parts of the brain.<ref name=Drugs2014/><ref name=NIH2016>{{cite web|title=DrugFacts: MDMA (Ecstasy/Molly)|url=https://www.drugabuse.gov/publications/drugfacts/mdma-ecstasymolly|website=National Institute on Drug Abuse|access-date=30 March 2016|date=February 2016|url-status=live|archive-url=https://web.archive.org/web/20160323164024/https://www.drugabuse.gov/publications/drugfacts/mdma-ecstasymolly|archive-date=23 March 2016|df=dmy-all}}</ref> It belongs to the [[substituted amphetamine]] [[chemical classification|classes of drugs]].<ref name=EU2015/><ref>{{cite book |vauthors=Freye E |title=Pharmacology and Abuse of Cocaine, Amphetamines, Ecstasy and Related Designer Drugs: A comprehensive review on their mode of action, treatment of abuse and intoxication |date=2009 |publisher=Springer Science & Business Media |isbn=978-90-481-2448-0 |page=147 |url=https://books.google.com/books?id=OTAlolM3XlwC&pg=PA147 |language=en |access-date=12 May 2020 |archive-date=13 January 2023 |archive-url=https://web.archive.org/web/20230113000534/https://books.google.com/books?id=OTAlolM3XlwC&pg=PA147 |url-status=live }}</ref> MDMA is structurally similar to [[mescaline]] (a psychedelic), methamphetamine (a stimulant), as well as [[Endogeny (biology)|endogenous]] [[monoamine neurotransmitter]]s such as serotonin, norepinephrine, and dopamine.<ref>{{cite journal | vauthors = Lyles J, Cadet JL | title = Methylenedioxymethamphetamine (MDMA, Ecstasy) neurotoxicity: cellular and molecular mechanisms | journal = Brain Research. Brain Research Reviews | volume = 42 | issue = 2 | pages = 155–168 | date = May 2003 | pmid = 12738056 | doi = 10.1016/S0165-0173(03)00173-5 | s2cid = 45330713 }}</ref>

<!-- Laws and research -->
MDMA has limited approved medical uses in a small number of countries,<ref>{{cite news |date=1 May 2018 |title=Ecstasy as a Remedy for PTSD? You Probably Have Some Questions. |url=https://www.nytimes.com/2018/05/01/us/ecstasy-molly-ptsd-mdma.html |url-access=limited |archive-url=https://ghostarchive.org/archive/20220101/https://www.nytimes.com/2018/05/01/us/ecstasy-molly-ptsd-mdma.html |archive-date=2022-01-01 |access-date=14 July 2018 |newspaper=The New York Times |language=en |vauthors=Philipps D}}{{cbignore}}</ref> but is illegal in most jurisdictions.<ref>{{cite book |url=https://books.google.com/books?id=8fihf3VWbcIC&pg=PA57 |title=Mental and neurological public health a global perspective |vauthors=Patel V |date=2010 |publisher=Academic Press/Elsevier |isbn=978-0-12-381527-9 |edition=1st |location=San Diego, CA |page=57 |archive-url=https://web.archive.org/web/20170910234523/https://books.google.com/books?id=8fihf3VWbcIC&pg=PA57 |archive-date=10 September 2017 |url-status=live |df=dmy-all}}</ref> In the United States, the [[Food and Drug Administration]] (FDA) is evaluating the drug for clinical use {{as of|2021|lc=y}}.<ref>{{cite web | title = A Psychedelic Drug Passes a Big Test for PTSD Treatment | work = The New York Times | vauthors = Nuwer R | author-link = Rachel Nuwer | date = 3 May 2021 | url = https://www.nytimes.com/2021/05/03/health/mdma-approval.html | access-date = 5 June 2021 | archive-date = 5 June 2021 | archive-url = https://web.archive.org/web/20210605190721/https://www.nytimes.com/2021/05/03/health/mdma-approval.html | url-status = live }}</ref> Canada has allowed limited distribution of MDMA upon application to and approval by [[Health Canada]].<ref>{{Cite web|work=Health Canada|date=2022-01-05|title=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|url=https://www.canada.ca/en/health-canada/services/health-concerns/controlled-substances-precursor-chemicals/policy-regulations/policy-documents/subsection-56-1-class-exemption-conducting-activities-psilocybin-mdma-special-access-program-authorization.html|access-date=2022-02-20|archive-date=11 February 2022|archive-url=https://web.archive.org/web/20220211203137/https://www.canada.ca/en/health-canada/services/health-concerns/controlled-substances-precursor-chemicals/policy-regulations/policy-documents/subsection-56-1-class-exemption-conducting-activities-psilocybin-mdma-special-access-program-authorization.html|url-status=live}}</ref><ref>{{Cite web |title=Canada approving psychedelics for therapy is a positive step, experts say - National |work=Globalnews.ca |url=https://globalnews.ca/news/8514429/psychedelic-drugs-therapy-canada/ |access-date=2022-02-20 |language=en-US |archive-date=20 February 2022 |archive-url=https://web.archive.org/web/20220220162212/https://globalnews.ca/news/8514429/psychedelic-drugs-therapy-canada/ |url-status=live }}</ref> In Australia, it may be prescribed in the treatment of PTSD by specifically authorised psychiatrists.<ref>{{Cite web |date=3 February 2023 |title=Change to classification of psilocybin and MDMA to enable prescribing by authorised psychiatrists |url=https://www.tga.gov.au/news/media-releases/change-classification-psilocybin-and-mdma-enable-prescribing-authorised-psychiatrists |access-date=4 February 2024 |archive-date=4 February 2024 |archive-url=https://web.archive.org/web/20240204024230/https://www.tga.gov.au/news/media-releases/change-classification-psilocybin-and-mdma-enable-prescribing-authorised-psychiatrists |url-status=live }}</ref>

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