Chemistry:Para-Methoxy-N-methylamphetamine

From HandWiki
Short description: Stimulant and psychedelic designer drug


para-Methoxy-N-methylamphetamine
4-Methoxymethamphetamine.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC11H17NO
Molar mass179.263 g·mol−1
3D model (JSmol)
  (verify)

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 stimulant and psychedelic drug closely related to the amphetamine-class serotonergic drug para-methoxyamphetamine (PMA). PMMA is the 4-methoxy analog of methamphetamine. Little is known about the pharmacological properties, metabolism, and toxicity 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.[1] In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.[2]

Its effects in humans are reputedly similar to those of PMA, but slightly more empathogenic in nature. It has a reduced tendency to produce severe hyperthermia at low dosages,[3][4] but at higher dosages side effects and risk of death become similar to those of PMA.[5]

The synthesis and effects of PMMA were described by American experimental chemist Alexander Shulgin in his book PiHKAL, where it is referred to by the name "methyl-MA", as the N-methylated form of 4-MA (PMA). Shulgin reported that PMMA produces an increase in blood pressure and in heart rate, at doses above 100 mg, but causes no psychoactive effects at these levels.

Recreational use

Tablets of PMMA recovered by the U.S. Drug Enforcement Administration

PMMA has been found in tablets and capsules of the MDMA 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.[6][7] 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 monoamine oxidase inhibitor (MAOI); if it is used in combination with MDMA or another MDMA-like substance, serotonin syndrome can result.[8]

PMMA can be detected with reagent testing kits.

Deaths

In January 2011, the Norwegian Broadcasting Corporation reported that Norway had seen 12 deaths related to PMMA over the course of six months. In March 2011, Dutch media reported that there had been four deaths in the province of Limburg since November 2010.[9] In April 2011, Icelandic media reported the death of a young woman that may have been connected to PMMA.[citation needed]

In 2011, four deaths were recorded in Scotland as a result of ecstasy tablets which also contained PMMA.[10]

In January 2012, a number of ecstasy-related deaths in Canada 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.[11][12][13][14][15][16]

In September 2012, the deaths of two men in County Cork, Ireland, have been linked to PMMA overdoses.[17] In the same month, the death of a man in Queensland, Australia was attributed to PMMA.[18]

In June 2013 a PMMA-related death occurred in the Dutch city of 's-Hertogenbosch.[19] Two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town of Sliedrecht.[20][21][22]

In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA.[23] In the same month, in Sweden, another man died from ecstasy laced with PMMA.[24]

In May 2015 a young woman died in Dublin, Ireland, after taking what is suspected to be PMMA.[25]

In April 2016 four young Argentina and one Uruguayan died during a massive rave called "Time Warp" in Buenos Aires and five more were hospitalized. PMMA was found in their bodies. [26]

Legal status

United States

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.[27]

United Kingdom

PMMA is controlled as a Schedule 1, Class A drug in the UK.[citation needed]

See also

References

  1. ↑ "A fatal paramethoxymethamphetamine intoxication". Legal Medicine. 5 5 (Suppl 1): S138-41. March 2003. doi:10.1016/s1344-6223(02)00096-2. PMID 12935573. 
  2. ↑ "Five B.C. deaths linked to lethal chemical PMMA". Vancouver Sun. 13 January 2012. https://vancouversun.com/news/calgary/Five+deaths+linked+lethal+chemical+PMMA/5993556/story.html. 
  3. ↑ "Initial characterization of PMMA as a discriminative stimulus". Pharmacology, Biochemistry, and Behavior 57 (1–2): 151–8. 1997. doi:10.1016/S0091-3057(96)00306-1. PMID 9164566. 
  4. ↑ "PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA". Pharmacology, Biochemistry, and Behavior 69 (1–2): 261–7. 2001. doi:10.1016/S0091-3057(01)00530-5. PMID 11420094. 
  5. ↑ "Three fatal cases of PMA and PMMA poisoning in Denmark". Journal of Analytical Toxicology 27 (4): 253–6. 2003. doi:10.1093/jat/27.4.253. PMID 12820749. 
  6. ↑ "Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects". Acta Anaesthesiologica Scandinavica 47 (10): 1298–9. November 2003. doi:10.1046/j.1399-6576.2003.00245.x. PMID 14616331. 
  7. ↑ "Fatal paramethoxy-amphetamine (PMA) poisoning in the Australian Capital Territory". The Medical Journal of Australia 188 (7): 426. April 2008. doi:10.5694/j.1326-5377.2008.tb01695.x. PMID 18393753. 
  8. ↑ "p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo". The Journal of Pharmacy and Pharmacology 32 (4): 262–6. April 1980. doi:10.1111/j.2042-7158.1980.tb12909.x. PMID 6103055. 
  9. ↑ "PMMA deaths in Holland". nu.nl. 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. 
  10. ↑ "Warning over ecstasy pills that raise overdose risk". BBC News. 16 December 2011. https://www.bbc.co.uk/news/uk-scotland-16224849. 
  11. ↑ "Rare chemical found in fatal ecstasy". The Province. 15 January 2012. https://theprovince.com/life/Rare+chemical+found+fatal+ecstasy/5998482/story.html. 
  12. ↑ "Overdose death investigated". Nanton News. 24 January 2012. http://www.nantonnews.com/ArticleDisplay.aspx?e=3446181. 
  13. ↑ "Seized substances sent for testing after suspected overdose". Calgary Herald. https://calgaryherald.com/news/alberta/Update+Seized+substances+sent+testing+after+suspected+overdose+SAIT/6037966/story.html. 
  14. ↑ "Tainted ecstasy linked to five Calgary deaths could be from B.C.". Vancouver Sun. 12 January 2012. https://vancouversun.com/touch/story.html?id=5980841. 
  15. ↑ "Authorities renew warning about street drugs". The City of Calgary Newsroom. http://newsroom.calgary.ca/pr/calgary/authorities-renew-warning-about-221684.aspx. 
  16. ↑ "Ecstasy laced with meth in overdose cases". http://www.cbc.ca/news/canada/calgary/story/2012/01/11/calgary-ecstasy-meth-deaths.html. 
  17. ↑ "Dangerous drug linked to Kinsale deaths". Irish Independent. 13 September 2012. http://www.irishtimes.com/newspaper/ireland/2012/0913/1224323959421.html. 
  18. ↑ "Queensland Police investigate three deaths linked to 'poison pill' ecstasy overdoses". news.com.au. 9 September 2012. http://www.news.com.au/national/queensland-police-investigate-three-deaths-linked-to-poison-pill-ecstasy-overdoses/story-fndo4ckr-1226468070006. 
  19. ↑ "Den Bosch issues a warning for dangerous XTC-pills". nu.nl. 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. 
  20. ↑ "Tiener overleden aan drugs". http://www.hetkompassliedrecht.nl/lokaal/tiener_overleden_aan_drugssliedrecht__in_sliedrecht_is_zondag_een_meisje_van_zestien_jaar_overleden_2526291.html. 
  21. ↑ "Naomi (16): dood door roze xtc-pil". 26 August 2013. http://www.misdaadjournalist.nl/2013/08/naomi-16-dood-door-roze-xtc-pil/. 
  22. ↑ "Waarschuwing: dodelijke 'XTC' in omloop". http://www.camilleri.nl/2013/08/waarschuwing-dodelijke-xtc-in-omloop/. 
  23. ↑ "Man charged after ecstasy deaths". BBC News. 15 May 2018. https://www.bbc.co.uk/news/uk-england-30671300. 
  24. ↑ "Varning för livsfarlig ecstasy" (in Swedish). 2 January 2015. http://www.aftonbladet.se/nyheter/article20103807.ab. 
  25. ↑ "Dublin student dies after taking PMMA tablets in nightclub". 17 May 2015. http://www.irishexaminer.com/breakingnews/ireland/dublin-student-dies-after-taking-pmma-tablets-in-nightclub-677531.html. 
  26. ↑ Himitian, Evangelina (17 April 2016). "Conmoción por la muerte de cinco jóvenes en una fiesta electrónica" (in Spanish). La Nación. http://www.lanacion.com.ar/1890177-conmocion-por-la-muerte-de-cinco-jovenes-en-una-fiesta-electronica. 
  27. ↑ "Schedules of Controlled Substances: Placement of para-Methoxymethamphetamine (PMMA) in Schedule I". June 25, 2021. https://www.federalregister.gov/documents/2021/06/25/2021-13460/schedules-of-controlled-substances-placement-of-para-methoxymethamphetamine-pmma-in-schedule-i. 

External links



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Para-Methoxy-N-methylamphetamine&oldid=3337134"