Editing MDMA (section)

==Chemistry==
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| caption = MDMA is a [[racemic mixture]] and exists as two [[enantiomers]]: [[(R)-MDMA|(''R'')-MDMA]] and (''S'')-MDMA.
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| alt = Racemic MDMA structure diagram
| image = (±)-MDMA-Formel Structural Formulae.svg
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{{Annotation|60|70|(''R'')-MDMA}}
{{Annotation|60|175|(''S'')-MDMA}}
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| image1 = White MDMA salt in a bag.jpg
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| alt1 = A powdered salt of MDMA
| caption1 = A powdered salt of MDMA

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| image2 = MDMAjakarta.jpg
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| alt2 = Reactors used in synthesis
| caption2 = Reactors used to synthesize MDMA on an industrial scale in a [[clandestine chemistry|clandestine chemical factory]] in Cikande, [[Indonesia]]
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MDMA is in the [[substituted methylenedioxyphenethylamine]] and [[substituted amphetamine]] [[chemical classification|classes of chemicals]]. As a [[free base]], MDMA is a colorless oil insoluble in water.<ref name=EU2015 /> The most common salt of MDMA is the hydrochloride salt;<ref name=EU2015 /> pure MDMA hydrochloride is water-soluble and appears as a white or off-white powder or crystal.<ref name=EU2015 />

===Synthesis===
There are numerous methods available to synthesize MDMA via different intermediates.<ref>{{cite journal | vauthors = Milhazes N, Martins P, Uriarte E, Garrido J, Calheiros R, Marques MP, Borges F | title = Electrochemical and spectroscopic characterisation of amphetamine-like drugs: application to the screening of 3,4-methylenedioxymethamphetamine (MDMA) and its synthetic precursors | journal = Analytica Chimica Acta | volume = 596 | issue = 2 | pages = 231–41 | date = July 2007 | pmid = 17631101 | doi = 10.1016/j.aca.2007.06.027 | bibcode = 2007AcAC..596..231M | hdl = 10316/45124 | hdl-access = free }}</ref><ref>{{cite journal | vauthors = Milhazes N, Cunha-Oliveira T, Martins P, Garrido J, Oliveira C, Rego AC, Borges F | title = Synthesis and cytotoxic profile of 3,4-methylenedioxymethamphetamine ("ecstasy") and its metabolites on undifferentiated PC12 cells: A putative structure-toxicity relationship | journal = Chemical Research in Toxicology | volume = 19 | issue = 10 | pages = 1294–304 | date = October 2006 | pmid = 17040098 | doi = 10.1021/tx060123i | hdl = 10316/12872 | url = https://estudogeral.sib.uc.pt/bitstream/10316/12872/1/Synthesis%20and%20Cytotoxic%20Profile.pdf | hdl-access = free | access-date = 24 September 2019 | archive-date = 28 June 2021 | archive-url = https://web.archive.org/web/20210628070418/https://estudogeral.sib.uc.pt/bitstream/10316/12872/1/Synthesis%20and%20Cytotoxic%20Profile.pdf | url-status = live }}</ref><ref>{{cite journal | vauthors = Baxter EW, Reitz AB |title = Reductive aminations of carbonyl compounds with borohydride and borane reducing agents. | journal = Organic Reactions | date = April 2004 | volume = 59 | page = 59 | location = Hoboken, New Jersey, United States | doi = 10.1002/0471264180.or059.01 |isbn = 0471264180 }}</ref><ref>{{cite journal | vauthors = Gimeno P, Besacier F, Bottex M, Dujourdy L, Chaudron-Thozet H | title = A study of impurities in intermediates and 3,4-methylenedioxymethamphetamine (MDMA) samples produced via reductive amination routes | journal = Forensic Science International | volume = 155 | issue = 2–3 | pages = 141–57 | date = December 2005 | pmid = 16226151 | doi = 10.1016/j.forsciint.2004.11.013 }}</ref> The original MDMA synthesis described in Merck's patent involves brominating [[safrole]] to 1-(3,4-methylenedioxyphenyl)-2-bromopropane and then reacting this adduct with methylamine.<ref>{{cite journal | vauthors = Palhol F, Boyer S, Naulet N, Chabrillat M | title = Impurity profiling of seized MDMA tablets by capillary gas chromatography | journal = Analytical and Bioanalytical Chemistry | volume = 374 | issue = 2 | pages = 274–81 | date = September 2002 | pmid = 12324849 | doi = 10.1007/s00216-002-1477-6 | s2cid = 42666306 }}</ref><ref>{{cite journal | vauthors = Renton RJ, Cowie JS, Oon MC | title = A study of the precursors, intermediates and reaction by-products in the synthesis of 3,4-methylenedioxymethylamphetamine and its application to forensic drug analysis | journal = Forensic Science International | volume = 60 | issue = 3 | pages = 189–202 | date = August 1993 | pmid = 7901132 | doi = 10.1016/0379-0738(93)90238-6 }}</ref> Most illicit MDMA is synthesized using [[MDP2P]] (3,4-methylenedioxyphenyl-2-propanone) as a precursor. MDP2P in turn is generally synthesized from [[piperonal]], [[safrole]] or [[isosafrole]].<ref name="World Drug Report 2014">{{cite book|title=World Drug Report 2014|date=June 2014|publisher=[[United Nations Office on Drugs and Crime]]|location=Vienna, Austria|isbn=978-92-1-056752-7|url=http://www.unodc.org/documents/wdr2014/World_Drug_Report_2014_web.pdf|access-date=1 December 2014|pages=2, 3, 123–152|veditors=Mohan J|archive-date=13 November 2014|archive-url=https://web.archive.org/web/20141113173315/http://www.unodc.org/documents/wdr2014/World_Drug_Report_2014_web.pdf|url-status=live}}</ref> One method is to [[Isomerization|isomerize]] safrole to isosafrole in the presence of a strong base, and then oxidize [[isosafrole]] to MDP2P. Another method uses the [[Wacker process]] to oxidize safrole directly to the MDP2P intermediate with a [[palladium]] catalyst. Once the MDP2P intermediate has been prepared, a [[reductive amination]] leads to [[racemic]] MDMA (an equal parts mixture of [[(R)-MDMA|(''R'')-MDMA]] and (''S'')-MDMA).{{citation needed|date=January 2015}} Relatively small quantities of essential oil are required to make large amounts of MDMA. The essential oil of ''[[Ocotea cymbarum]]'', for example, typically contains between 80 and 94% safrole. This allows 500{{nbsp}}mL of the oil to produce between 150 and 340 grams of MDMA.<ref>{{cite journal | url = https://www.justice.gov/dea/pr/micrograms/2005/mg1105.pdf | date = 11 November 2005 | title = Early Warning - MDMA and MDA Producers Using Ocotea Cymbarum as a Precursor | journal = DEA Microgram Newsletter | volume = 38 | issue = 11 | page = 166 | archive-url = https://web.archive.org/web/20121018052300/http://www.justice.gov/dea/pr/micrograms/2005/mg1105.pdf | archive-date=18 October 2012 | publisher = Drug Enforcement Agency, U.S. Department of Justice }}</ref>

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| image1 = MDMA Synthesis 1.svg
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| alt1 = Synthesis of MDMA from piperonal
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| alt2 = Synthesis of MDMA from piperonal
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| alt3 = Synthesis of MDMA and related analogs from safrole
| caption3 = Synthesis of MDMA and related analogs from safrole
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===Detection in body fluids===
MDMA and MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with MDMA or its major metabolites, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10% those of the parent drug.<ref name = "Kolbrich_2008" /><ref>{{cite journal | vauthors = Barnes AJ, De Martinis BS, Gorelick DA, Goodwin RS, Kolbrich EA, Huestis MA | title = Disposition of MDMA and metabolites in human sweat following controlled MDMA administration | journal = Clinical Chemistry | volume = 55 | issue = 3 | pages = 454–62 | date = March 2009 | pmid = 19168553 | pmc = 2669283 | doi = 10.1373/clinchem.2008.117093 }}</ref><ref>{{cite book | vauthors = Baselt RC |title=Disposition of toxic drugs and chemicals in man |date=2011 |publisher=Biomedical Publications |location=Seal Beach, Ca. |isbn=978-0-9626523-8-7 |edition=9th | pages = 1078–1080 }}</ref>

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