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para-Methoxy-N-methylamphetamine

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para-Methoxy-N-methylamphetamine
Legal status
Legal status
Identifiers
  • 1-(4-Methoxyphenyl)-N-methylpropan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
ECHA InfoCard100.040.818Edit this at Wikidata
Chemical and physical data
FormulaC11H17NO
Molar mass179.263g·mol−1
3D model (JSmol)
  • CC(CC1=CC=C(C=C1)OC)NC

  • C1=CC(=CC=C1CC(C)NC)OC
  • InChI=1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3
  • Key:UGFMBZYKVQSQFX-UHFFFAOYSA-N
(verify)

para-Methoxy-N-methylamphetamine(also known asPMMA,Red Mitsubishi), chemically known asmethyl-MA,4-methoxy-N-methylamphetamine,and4-MMA(or 4-PMDA, as listed to its original physical name) is astimulantandpsychedelic drugclosely related to theamphetamine-classserotonergicdrugpara-methoxyamphetamine(PMA). PMMA is the 4-methoxyanalogofmethamphetamine.Little is known about thepharmacologicalproperties,metabolism,andtoxicityof 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.[2]In the early 2010s, a number of deaths in users of the drugMDMAwere linked to misrepresented tablets and capsules of PMMA.[3]

Its effects in humans are reputedly similar to those of PMA, but slightly moreempathogenicin nature.[medical citation needed]It has a reduced tendency to produce severehyperthermiaat low dosages,[4][5]but at higher dosages side effects and risk of death become similar to those of PMA.[6]

The synthesis and effects of PMMA were described by American experimental chemistAlexander Shulginin his bookPiHKAL,where it is referred to by the name "methyl-MA", as theN-methylatedform of 4-MA (PMA). Shulgin reported that PMMA produces an increase inblood pressureand inheart rate,at doses above 100 mg, but causes nopsychoactiveeffects at these levels.

Recreational use[edit]

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

PMMA has been found in tablets and capsules of theMDMAsold 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.[7][8]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 amonoamine oxidase inhibitor (MAOI);if it is used in combination with MDMA or another MDMA-like substance,serotonin syndromecan result.[9]

PMMA can be detected withreagent testingkits.

Deaths[edit]

In January 2011, theNorwegian Broadcasting Corporationreported that Norway had seen 12 deaths related to PMMA over the course of six months. In March 2011,Dutchmedia reported that there had been four deaths in the province ofLimburgsince November 2010.[10]In April 2011,Icelandicmedia 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.[11]

In January 2012, a number of ecstasy-related deaths inCanadain 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.[12][13][14][15][16][17]

In September 2012, the deaths of two men inCounty Cork,Ireland,have been linked to PMMA overdoses.[18]In the same month, the death of a man in Queensland, Australia was attributed to PMMA.[19]

In June 2013 a PMMA-related death occurred in the Dutch city of's-Hertogenbosch.[20] Two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town ofSliedrecht.[21][22][23]

In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA.[24]In the same month, in Sweden, another man died from ecstasy laced with PMMA.[25]

In May 2015 a young woman died inDublin,Ireland, after taking what is suspected to be PMMA.[26]

In April 2016 four youngArgentinesand oneUruguayandied during a massive rave called "Time Warp" inBuenos Airesand five more were hospitalized. PMMA was found in their bodies. [27]

Legal status[edit]

United States[edit]

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.[28]

United Kingdom[edit]

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

See also[edit]

References[edit]

  1. ^Anvisa(24 July 2023)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"[Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União(published 25 July 2023).Archivedfrom the original on 27 August 2023.Retrieved27 August2023.
  2. ^Becker J, Neis P, Röhrich J, Zörntlein S (March 2003). "A fatal paramethoxymethamphetamine intoxication".Legal Medicine.5.5(Suppl 1): S138-41.doi:10.1016/s1344-6223(02)00096-2.PMID12935573.
  3. ^"Five B.C. deaths linked to lethal chemical PMMA".Vancouver Sun. 13 January 2012.
  4. ^Glennon RA, Young R, Dukat M, Cheng Y (1997). "Initial characterization of PMMA as a discriminative stimulus".Pharmacology, Biochemistry, and Behavior.57(1–2): 151–8.doi:10.1016/S0091-3057(96)00306-1.PMID9164566.S2CID28758326.
  5. ^Rangisetty JB, Bondarev ML, Chang-Fong J, Young R, Glennon RA (2001). "PMMA-stimulus generalization to the optical isomers of MBDB and 3,4-DMA".Pharmacology, Biochemistry, and Behavior.69(1–2): 261–7.doi:10.1016/S0091-3057(01)00530-5.PMID11420094.S2CID41953749.
  6. ^Johansen SS, Hansen AC, Müller IB, Lundemose JB, Franzmann MB (2003)."Three fatal cases of PMA and PMMA poisoning in Denmark".Journal of Analytical Toxicology.27(4): 253–6.doi:10.1093/jat/27.4.253.PMID12820749.S2CID42519181.
  7. ^Refstad S (November 2003)."Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects".Acta Anaesthesiologica Scandinavica.47(10): 1298–9.doi:10.1046/j.1399-6576.2003.00245.x.PMID14616331.S2CID28006785.
  8. ^Lamberth PG, Ding GK, Nurmi LA (April 2008). "Fatal paramethoxy-amphetamine (PMA) poisoning in the Australian Capital Territory".The Medical Journal of Australia.188(7): 426.doi:10.5694/j.1326-5377.2008.tb01695.x.PMID18393753.S2CID11987961.
  9. ^Green AL, El Hait MA (April 1980). "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.doi:10.1111/j.2042-7158.1980.tb12909.x.PMID6103055.S2CID42213032.
  10. ^"PMMA deaths in Holland".nu.nl.Retrieved8 June2011.
  11. ^"Warning over ecstasy pills that raise overdose risk".BBC News. 16 December 2011.Archivedfrom the original on 25 April 2012.
  12. ^"Rare chemical found in fatal ecstasy".The Province. 15 January 2012. Archived fromthe originalon 17 January 2012.Retrieved12 January2012.
  13. ^"Overdose death investigated".Nanton News. 24 January 2012.
  14. ^"Seized substances sent for testing after suspected overdose".Calgary Herald.Archived fromthe originalon 27 January 2012.Retrieved24 January2012.
  15. ^"Tainted ecstasy linked to five Calgary deaths could be from B.C."Vancouver Sun. 12 January 2012.Archivedfrom the original on 4 March 2013.Retrieved12 January2012.
  16. ^"Authorities renew warning about street drugs".The City of Calgary Newsroom. Archived fromthe originalon 15 January 2012.Retrieved11 January2012.
  17. ^"Ecstasy laced with meth in overdose cases".Archivedfrom the original on 12 January 2012.Retrieved12 January2012.
  18. ^"Dangerous drug linked to Kinsale deaths".Irish Independent.13 September 2012.Archivedfrom the original on 13 September 2012.Retrieved13 September2012.
  19. ^"Queensland Police investigate three deaths linked to 'poison pill' ecstasy overdoses".news.com.au. 9 September 2012.Retrieved30 September2012.
  20. ^"Den Bosch issues a warning for dangerous XTC-pills".nu.nl.Retrieved12 June2013.
  21. ^"Tiener overleden aan drugs".Archived fromthe originalon 29 August 2013.Retrieved30 August2013.
  22. ^"Naomi (16): dood door roze xtc-pil".26 August 2013.Archivedfrom the original on 29 August 2013.Retrieved26 August2013.
  23. ^"Waarschuwing: dodelijke 'XTC' in omloop".Archived fromthe originalon 29 August 2013.Retrieved26 August2013.
  24. ^"Man charged after ecstasy deaths".BBC News.15 May 2018.Archivedfrom the original on 13 May 2018.
  25. ^"Varning för livsfarlig ecstasy"(in Swedish). 2 January 2015.Archivedfrom the original on 5 January 2015.Retrieved4 January2015.
  26. ^"Dublin student dies after taking PMMA tablets in nightclub".irishexaminer.com.17 May 2015.Archivedfrom the original on 18 May 2015.
  27. ^Himitian, Evangelina (17 April 2016)."Conmoción por la muerte de cinco jóvenes en una fiesta electrónica".La Nación(in Spanish).Archivedfrom the original on 19 April 2016.
  28. ^"Schedules of Controlled Substances: Placement of para-Methoxymethamphetamine (PMMA) in Schedule I".federalregister.gov.25 June 2021.

External links[edit]

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