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{{Short description|Stimulant and psychedelic designer drug}} |
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{{DISPLAYTITLE:''para''-Methoxymethamphetamine}} |
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{{DISPLAYTITLE:''para''-Methoxy-''N''-methylamphetamine}} |
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{{Use dmy dates|date=March 2020}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 447762042 |
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| verifiedrevid = 449584234 |
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| IUPAC_name = 1-(4-methoxyphenyl)-''N''-methyl-propan-2-amine |
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| IUPAC_name = 1-(4-Methoxyphenyl)-''N''-methylpropan-2-amine |
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| image = 4-Methoxymethamphetamine.svg |
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| image = 4-Methoxymethamphetamine.svg |
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| width = 250 |
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| width = 200 |
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| drug_name = ''para''-Methoxymethamphetamine |
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| drug_name = ''para''-Methoxy-''N''-methylamphetamine |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> |
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| legal_status = Controlled under Federal Analog Act |
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| legal_BR = F2 |
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| 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=] |language=pt-BR |publication-date=2023-07-25}}</ref> |
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| legal_CA = Schedule I |
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| legal_DE = Anlage I |
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| legal_US = Schedule 1 |
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| legal_US_comment = |
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| legal_UK = Class A |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| index_label = |
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| CAS_number = 3398-68-3 |
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| index2_label = |
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| CAS_number_Ref = {{cascite|correct|CAS}} |
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| CAS_number = 22331-70-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 037U5SR9KL |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C22810 |
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| PubChem = 90766 |
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| PubChem = 90766 |
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| ChemSpiderID = 81951 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=11 | H=17 | N=1 | O=1 |
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| C=11 | H=17 | N=1 | O=1 |
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| smiles2 = C1=CC(=CC=C1CC(C)NC)OC |
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| molecular_weight = 179.259 g/mol |
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| smiles = C1=CC(=CC=C1CC(C)NC)OC |
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| smiles = CC(CC1=CC=C(C=C1)OC)NC |
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| StdInChI = 1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3 |
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| StdInChIKey = UGFMBZYKVQSQFX-UHFFFAOYSA-N |
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}} |
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}} |
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'''''para''-Methoxy-''N''-methylamphetamine''' (also known as '''PMMA''', '''Red Mitsubishi'''), chemically known as '''methyl-MA''', '''4-methoxy-''N''-methylamphetamine''', and '''4-MMA''' (or 4-PMDA, as listed to its original physical name) is a ] and ] closely related to the ]-class ] drug ] (PMA). PMMA is the 4-] ] of ]. Little is known about the ] properties, ], and ] of PMMA; because of its structural similarity to PMA, which has known toxicity in humans, it is thought to have considerable potential to cause harmful side effects or death in overdose.<ref>{{cite journal | vauthors = Becker J, Neis P, Röhrich J, Zörntlein S | title = A fatal paramethoxymethamphetamine intoxication | journal = Legal Medicine | volume = 5 | pages = S138-41 | date = March 2003 | pmid = 12935573 | doi = 10.1016/s1344-6223(02)00096-2 | series = 5 | issue = Suppl 1 }}</ref> In the early 2010s, a number of deaths in users of the drug ] were linked to misrepresented tablets and capsules of PMMA.<ref>{{Cite web | url = https://vancouversun.com/news/five-bc-deaths-linked-to-lethal-chemical-pmma| title = Five B.C. deaths linked to lethal chemical PMMA | date = 10 January 2012 | publisher = Vancouver Sun}}</ref> |
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'''''para''-Methoxymethamphetamine''' ('''PMMA'''), is a ] ] related to ] (PMA). |
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Its effects in humans are reputedly similar to those of PMA, but slightly more ] in nature.{{Medcn|date=January 2015}} It has a reduced tendency to produce severe ] at low dosages,<ref>{{Cite journal | vauthors = Glennon RA, Young R, Dukat M, Cheng Y | title = Initial characterization of PMMA as a discriminative stimulus | journal = Pharmacology, Biochemistry, and Behavior | volume = 57 | issue = 1–2 | pages = 151–8 | year = 1997 | pmid = 9164566 | doi = 10.1016/S0091-3057(96)00306-1 | s2cid = 28758326 }}</ref><ref>{{cite journal | vauthors = Rangisetty JB, Bondarev ML, Chang-Fong J, Young R, Glennon RA | title = PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA | journal = Pharmacology, Biochemistry, and Behavior | volume = 69 | issue = 1–2 | pages = 261–7 | year = 2001 | pmid = 11420094 | doi = 10.1016/S0091-3057(01)00530-5 | s2cid = 41953749 }}</ref> but at higher dosages side effects and risk of death become similar to those of PMA.<ref>{{cite journal | vauthors = Johansen SS, Hansen AC, Müller IB, Lundemose JB, Franzmann MB | title = Three fatal cases of PMA and PMMA poisoning in Denmark | journal = Journal of Analytical Toxicology | volume = 27 | issue = 4 | pages = 253–6 | year = 2003 | pmid = 12820749 | doi = 10.1093/jat/27.4.253 | s2cid = 42519181 | doi-access = free }}</ref> |
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]]] |
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The synthesis and effects of PMMA were described by American experimental chemist ] in his book '']'', where it is referred to by the name "methyl-MA", as the ] form of 4-MA (PMA). Shulgin reported that PMMA produces an increase in ] and in ], at doses above 100 mg, but causes no ] effects at these levels. |
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PMMA reputedly produces similar effects to PMA, but is apparently slightly more similar to ] in effects<ref>{{cite journal|doi=10.1016/S0091-3057(96)00306-1|pmid=9164566|year=1997|last1=Glennon|first1=RA|last2=Young|first2=R|last3=Dukat|first3=M|last4=Cheng|first4=Y|title=Initial characterization of PMMA as a discriminative stimulus|volume=57|issue=1-2|pages=151–8|journal=Pharmacology, biochemistry, and behavior}}</ref><ref>{{cite journal|doi=10.1016/S0091-3057(01)00530-5|pmid=11420094|year=2001|last1=Rangisetty|first1=JB|last2=Bondarev|first2=ML|last3=Chang-Fong|first3=J|last4=Young|first4=R|last5=Glennon|first5=RA|title=PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA|volume=69|issue=1-2|pages=261–7|journal=Pharmacology, biochemistry, and behavior}}</ref> and has slightly less tendency to produce severe ], at least at low doses. At higher doses however the side effects and danger of death are just as severe as those of PMA itself.<ref>{{cite journal|pmid=12820749|year=2003|last1=Johansen|first1=SS|last2=Hansen|first2=AC|last3=Müller|first3=IB|last4=Lundemose|first4=JB|last5=Franzmann|first5=MB|title=Three fatal cases of PMA and PMMA poisoning in Denmark|volume=27|issue=4|pages=253–6|journal=Journal of analytical toxicology}}</ref> |
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==Pharmacology== |
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PMMA is a lesser-known ]. It is the 4-] ] of methamphetamine. PMMA was probably first synthesized by ]. In his book '']'', the minimum dosage is listed as 100 mg, and the duration unknown. Shulgin reported that methyl-MA produces an increase in ] and in ], but causes no ] effects, however user reports following the subsequent appearance of this drug on the illicit market as an analogue of "Ecstasy" (]) suggest that PMMA does produce some ]ic effects. Very little data exists about the pharmacological properties, metabolism, and toxicity of PMMA, and given the known toxicity of the related compound PMA it is likely to have considerable potential to cause harmful side effects or overdose which can be fatal.<ref>{{cite journal|pmid=12935573|year=2003|last1=Becker|first1=J|last2=Neis|first2=P|last3=Röhrich|first3=J|last4=Zörntlein|first4=S|title=A fatal paramethoxymethamphetamine intoxication|volume=Suppl 1|series=5|pages=S138–41|journal=Legal medicine (Tokyo, Japan)}}</ref> |
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PMMA is a ] (MAO-A) ].<ref name="Reyes-ParadaIturriaga-VasquezCassels2019">{{cite journal | vauthors = Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK | title = Amphetamine Derivatives as Monoamine Oxidase Inhibitors | journal = Front Pharmacol | volume = 10 | issue = | pages = 1590 | date = 2019 | pmid = 32038257 | pmc = 6989591 | doi = 10.3389/fphar.2019.01590 | doi-access = free | url = }}</ref> Its {{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}} for MAO-A inhibition has been reported to be 1,700{{nbsp}}nM.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019" /> |
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==Reported deaths== |
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==Recreational use== |
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]]] |
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{{Unreferenced section|date=May 2011}} |
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31 January 2011 the ] reported that Norway had seen a staggering 12 deaths related to this drug in just 6 months. |
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PMMA has been found in tablets and capsules of the ] sold as "ecstasy". A number of deaths have been attributed to tablets sold as ecstasy that contained other substances, such as PMMA's structural analog, PMA.<ref>{{cite journal | vauthors = Refstad S | title = Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects | journal = Acta Anaesthesiologica Scandinavica | volume = 47 | issue = 10 | pages = 1298–9 | date = November 2003 | pmid = 14616331 | doi = 10.1046/j.1399-6576.2003.00245.x | s2cid = 28006785 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Lamberth PG, Ding GK, Nurmi LA | title = Fatal paramethoxy-amphetamine (PMA) poisoning in the Australian Capital Territory | journal = The Medical Journal of Australia | volume = 188 | issue = 7 | pages = 426 | date = April 2008 | pmid = 18393753 | doi = 10.5694/j.1326-5377.2008.tb01695.x | s2cid = 11987961 }}</ref> Death can occur when an ecstasy user believes they are consuming recreational doses of MDMA, when they are in fact consuming a lethal dose of another substance with similar effects. PMA is of particular concern because it not only causes a release of serotonin but also acts as a ]; if it is used in combination with MDMA or another MDMA-like substance, ] can result.<ref>{{cite journal | vauthors = Green AL, El Hait MA | title = p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo | journal = The Journal of Pharmacy and Pharmacology | volume = 32 | issue = 4 | pages = 262–6 | date = April 1980 | pmid = 6103055 | doi = 10.1111/j.2042-7158.1980.tb12909.x | s2cid = 42213032 }}</ref> |
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31 March 2011 Dutch media reported that the Netherlands (Limburg province) had seen 4 deaths related to this drug since November 2010.<ref>{{cite web|title=PMMA deaths in Holland|url=http://translate.google.com/translate?js=n&prev=_t&hl=nl&ie=UTF-8&layout=2&eotf=1&sl=nl&tl=en&u=http%3A%2F%2Fwww.nu.nl%2Fbinnenland%2F2535695%2Fpinkpopgangers-moeten-uitkijken-met-xtc.html|publisher=www.nu.nl|accessdate=8 June 2011}}</ref> |
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PMMA can be detected with ] kits. |
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30 April 2011 Icelandic media reported that Iceland had seen 1 death of a young woman that may have been related to this drug. |
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==See also== |
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===Deaths=== |
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{{excessive examples|date=November 2019}} |
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*] (PMA) |
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*] (Methoxyphenamine) |
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*] (MMMA) |
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*] (4-FMA) |
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*] (4-MMA) |
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*] (bk-PMMA) |
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In January 2011, the ] reported that Norway had seen 12 deaths related to PMMA over the course of six months. In March 2011, ] media reported that there had been four deaths in the province of ] since November 2010.<ref>{{cite web|title=PMMA deaths in Holland|url=https://translate.google.com/translate?js=n&prev=_t&hl=en&ie=UTF-8&layout=2&eotf=1&sl=nl&tl=en&u=http%3A%2F%2Fwww.nu.nl%2Fbinnenland%2F2535695%2Fpinkpopgangers-moeten-uitkijken-met-xtc.html|publisher=nu.nl|access-date=8 June 2011}}</ref> In April 2011, ]ic media reported the death of a young woman that may have been connected to PMMA.{{Citation needed|date=February 2012}} |
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==External links== |
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In 2011, four deaths were recorded in Scotland as a result of ecstasy tablets which also contained PMMA.<ref>{{cite web | url = https://www.bbc.co.uk/news/uk-scotland-16224849 | title = Warning over ecstasy pills that raise overdose risk | date = 16 December 2011 | publisher = BBC News | url-status = live | archive-url = https://web.archive.org/web/20120425143045/http://www.bbc.co.uk/news/uk-scotland-16224849 | archive-date = 25 April 2012}}</ref> |
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In January 2012, a number of ecstasy-related deaths in ] in the previous year were linked to PMMA overdoses. In the single year, approximately 45 exposures occurred, resulting in 21 deaths. Cases were centred primarily in Calgary and Vancouver.<ref>{{cite web | url = https://theprovince.com/life/Rare+chemical+found+fatal+ecstasy/5998482/story.html | archive-url = https://web.archive.org/web/20120117004747/http://www.theprovince.com/life/Rare+chemical+found+fatal+ecstasy/5998482/story.html | url-status = dead | archive-date = 17 January 2012 | publisher = The Province | date = 15 January 2012 | access-date = 12 January 2012 | title = Rare chemical found in fatal ecstasy}}</ref><ref>{{cite web | url = http://www.nantonnews.com/ArticleDisplay.aspx?e=3446181 | publisher = Nanton News | title = Overdose death investigated | date = 24 January 2012}}</ref><ref>{{cite web |url=https://calgaryherald.com/news/alberta/Update+Seized+substances+sent+testing+after+suspected+overdose+SAIT/6037966/story.html |work=Calgary Herald|title=Seized substances sent for testing after suspected overdose |access-date=24 January 2012 |url-status=dead |archive-url=https://web.archive.org/web/20120127040640/http://www.calgaryherald.com/news/alberta/Update+Seized+substances+sent+testing+after+suspected+overdose+SAIT/6037966/story.html |archive-date=27 January 2012}}</ref><ref>{{cite web | url = https://vancouversun.com/touch/story.html?id=5980841 | title = Tainted ecstasy linked to five Calgary deaths could be from B.C. | publisher = Vancouver Sun | date = 12 January 2012 | access-date = 12 January 2012 | url-status = live | archive-url = https://web.archive.org/web/20130304085614/http://www.vancouversun.com/touch/story.html?id=5980841 | archive-date = 4 March 2013}}</ref><ref>{{cite web |title=Authorities renew warning about street drugs |url=http://newsroom.calgary.ca/pr/calgary/authorities-renew-warning-about-221684.aspx |publisher=The City of Calgary Newsroom |access-date=11 January 2012 |url-status=dead |archive-url=https://web.archive.org/web/20120115072845/http://newsroom.calgary.ca/pr/calgary/authorities-renew-warning-about-221684.aspx |archive-date=15 January 2012}}</ref><ref>{{cite web|title=Ecstasy laced with meth in overdose cases|url=https://www.cbc.ca/news/canada/calgary/ecstasy-laced-with-meth-blamed-in-5-calgary-deaths-1.1162942|access-date=12 January 2012|url-status=live|archive-url=https://web.archive.org/web/20120112020050/http://www.cbc.ca/news/canada/calgary/story/2012/01/11/calgary-ecstasy-meth-deaths.html|archive-date=12 January 2012}}</ref> |
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In September 2012, the deaths of two men in ], ], have been linked to PMMA overdoses.<ref>{{cite web | url = http://www.irishtimes.com/newspaper/ireland/2012/0913/1224323959421.html | title = Dangerous drug linked to Kinsale deaths | work = Irish Independent| date = 13 September 2012 | access-date = 13 September 2012 | url-status = live | archive-url = https://web.archive.org/web/20120913021332/http://www.irishtimes.com/newspaper/ireland/2012/0913/1224323959421.html | archive-date = 13 September 2012}}</ref> In the same month, the death of a man in Queensland, Australia was attributed to PMMA.<ref>{{cite web | url = http://www.news.com.au/national/queensland-police-investigate-three-deaths-linked-to-poison-pill-ecstasy-overdoses/story-fndo4ckr-1226468070006 | title = Queensland Police investigate three deaths linked to 'poison pill' ecstasy overdoses | publisher = news.com.au | date = 9 September 2012 | access-date = 30 September 2012}}</ref> |
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In June 2013 a PMMA-related death occurred in the Dutch city of ].<ref>{{cite web|title=Den Bosch issues a warning for dangerous XTC-pills|url=https://translate.google.com/translate?js=n&prev=_t&hl=en&ie=UTF-8&layout=2&eotf=1&sl=nl&tl=en&u=http%3A%2F%2Fwww.nu.nl%2Fbinnenland%2F3498768%2Fbosch-waarschuwt-gevaarlijke-xtc-pillen.html|publisher=nu.nl|access-date=12 June 2013}}</ref> |
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Two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town of ].<ref>{{cite web | url=http://www.hetkompassliedrecht.nl/lokaal/tiener_overleden_aan_drugssliedrecht__in_sliedrecht_is_zondag_een_meisje_van_zestien_jaar_overleden_2526291.html | title=Tiener overleden aan drugs | access-date=30 August 2013 | url-status=dead | archive-url=https://web.archive.org/web/20130829114721/http://www.hetkompassliedrecht.nl/lokaal/tiener_overleden_aan_drugssliedrecht__in_sliedrecht_is_zondag_een_meisje_van_zestien_jaar_overleden_2526291.html | archive-date=29 August 2013 }}</ref><ref>{{cite web|url=http://www.misdaadjournalist.nl/2013/08/naomi-16-dood-door-roze-xtc-pil/|title=Naomi (16): dood door roze xtc-pil|access-date=26 August 2013|url-status=live|archive-url=https://web.archive.org/web/20130829063908/http://www.misdaadjournalist.nl/2013/08/naomi-16-dood-door-roze-xtc-pil/|archive-date=29 August 2013|date=26 August 2013}}</ref><ref>{{cite web |url=http://www.camilleri.nl/2013/08/waarschuwing-dodelijke-xtc-in-omloop/ |title=Waarschuwing: dodelijke 'XTC' in omloop |access-date=26 August 2013 |url-status=dead |archive-url=https://web.archive.org/web/20130829040737/http://www.camilleri.nl/2013/08/waarschuwing-dodelijke-xtc-in-omloop |archive-date=29 August 2013}}</ref> |
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In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA.<ref>{{cite news|url=https://www.bbc.co.uk/news/uk-england-30671300|title=Man charged after ecstasy deaths|date=15 May 2018|url-status=live|archive-url=https://web.archive.org/web/20180513000438/http://www.bbc.co.uk/news/uk-england-30671300|archive-date=13 May 2018|work=BBC News}}</ref> In the same month, in Sweden, another man died from ecstasy laced with PMMA.<ref>{{cite web | url=http://www.aftonbladet.se/nyheter/article20103807.ab | title=Varning för livsfarlig ecstasy | date=2 January 2015 | access-date=4 January 2015 | language=Swedish | url-status=live | archive-url=https://web.archive.org/web/20150105014657/http://www.aftonbladet.se/nyheter/article20103807.ab | archive-date=5 January 2015}}</ref> |
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In May 2015 a young woman died in ], Ireland, after taking what is suspected to be PMMA.<ref>{{cite web|url=http://www.irishexaminer.com/breakingnews/ireland/dublin-student-dies-after-taking-pmma-tablets-in-nightclub-677531.html|title=Dublin student dies after taking PMMA tablets in nightclub|date=17 May 2015|website=irishexaminer.com|url-status=live|archive-url=https://web.archive.org/web/20150518114230/http://www.irishexaminer.com/breakingnews/ireland/dublin-student-dies-after-taking-pmma-tablets-in-nightclub-677531.html|archive-date=18 May 2015}}</ref> |
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In April 2016 four young ] and one ]an died during a massive rave called "Time Warp" in ] and five more were hospitalized. PMMA was found in their bodies. |
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<ref>{{cite news|url=http://www.lanacion.com.ar/1890177-conmocion-por-la-muerte-de-cinco-jovenes-en-una-fiesta-electronica|title=Conmoción por la muerte de cinco jóvenes en una fiesta electrónica|newspaper=La Nación|language=Spanish|date=17 April 2016|url-status=live|archive-url=https://web.archive.org/web/20160419003155/http://www.lanacion.com.ar/1890177-conmocion-por-la-muerte-de-cinco-jovenes-en-una-fiesta-electronica|archive-date=19 April 2016|last1=Himitian|first1=Evangelina}}</ref> |
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==Legal status== |
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===United States=== |
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On June 25, 2021 the DEA finalized a rule placing PMMA on the Controlled Substance Act federal Schedule as a Schedule I substance effective July 26, 2021.<ref name="DEA Schedules PMMA as Schedule I">{{cite web|url=https://www.federalregister.gov/documents/2021/06/25/2021-13460/schedules-of-controlled-substances-placement-of-para-methoxymethamphetamine-pmma-in-schedule-i |title=Schedules of Controlled Substances: Placement of para-Methoxymethamphetamine (PMMA) in Schedule I |website=federalregister.gov |date=June 25, 2021}}</ref> |
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===United Kingdom=== |
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PMMA is controlled as a Schedule 1, ] in the UK.{{citation needed|date=July 2016}} |
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== See also == |
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* ] (PMA) |
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* ] (Methoxyphenamine) |
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* ] (MMMA) |
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* ] (4-FMA) |
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* ] (4-MMA) |
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* ] (bk-PMMA) |
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* ] |
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== References == |
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{{reflist|30em}} |
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== External links == |
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==References== |
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{{reflist|2}} |
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{{Monoamine releasing agents}} |
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{{PiHKAL}} |
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{{Monoamine metabolism modulators}} |
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{{Stimulants}} |
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{{Dopaminergics}} |
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{{Phenethylamines}} |
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{{Serotonergics}} |
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{{Amphetamines}} |
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{{Use dmy dates|date=May 2011}} |
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{{DEFAULTSORT:Methoxymethamphetamine, para-}} |
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{{DEFAULTSORT:Methoxy-N-methylamphetamine, para-}} |
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{{nervous-system-drug-stub}} |
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] |
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