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para-Methoxy-N-methylamphetamine

April 09, 2024

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.[2] In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA.[3]

para-Methoxy-N-methylamphetamine
Legal status
Legal status
Identifiers
  • 1-(4-Methoxyphenyl)-N-methylpropan-2-amine
CAS Number
  • 22331-70-0 Y
PubChem CID
  • 90766
ChemSpider
  • 81951
UNII
  • 037U5SR9KL
KEGG
  • C22810 Y
CompTox Dashboard (EPA)
  • DTXSID30874251
ECHA InfoCard100.040.818
Chemical and physical data
FormulaC11H17NO
Molar mass179.263 g·mol−1
3D model (JSmol)
  • Interactive image
  • Interactive image
  • 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)

Its effects in humans are reputedly similar to those of PMA, but slightly more empathogenic in nature.[medical citation needed] It has a reduced tendency to produce severe hyperthermia at 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 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 edit

 
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.[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 a monoamine oxidase inhibitor (MAOI); if it is used in combination with MDMA or another MDMA-like substance, serotonin syndrome can result.[9]

PMMA can be detected with reagent testing kits.

Deaths edit

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.[10] 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.[11]

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.[12][13][14][15][16][17]

In September 2012, the deaths of two men in County 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 of Sliedrecht.[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 in Dublin, Ireland, after taking what is suspected to be PMMA.[26]

In April 2016 four young Argentines 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. [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 drug in 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). from the original on 27 August 2023. Retrieved 27 August 2023.
  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. PMID 12935573.
  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. PMID 9164566. S2CID 28758326.
  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. PMID 11420094. S2CID 41953749.
  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. PMID 12820749. S2CID 42519181.
  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. PMID 14616331. S2CID 28006785.
  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. PMID 18393753. S2CID 11987961.
  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. PMID 6103055. S2CID 42213032.
  10. ^ "PMMA deaths in Holland". nu.nl. Retrieved 8 June 2011.
  11. ^ "Warning over ecstasy pills that raise overdose risk". BBC News. 16 December 2011. from the original on 25 April 2012.
  12. ^ . The Province. 15 January 2012. Archived from the original on 17 January 2012. Retrieved 12 January 2012.
  13. ^ "Overdose death investigated". Nanton News. 24 January 2012.
  14. ^ . Calgary Herald. Archived from the original on 27 January 2012. Retrieved 24 January 2012.
  15. ^ "Tainted ecstasy linked to five Calgary deaths could be from B.C." Vancouver Sun. 12 January 2012. from the original on 4 March 2013. Retrieved 12 January 2012.
  16. ^ . The City of Calgary Newsroom. Archived from the original on 15 January 2012. Retrieved 11 January 2012.
  17. ^ "Ecstasy laced with meth in overdose cases". from the original on 12 January 2012. Retrieved 12 January 2012.
  18. ^ "Dangerous drug linked to Kinsale deaths". Irish Independent. 13 September 2012. from the original on 13 September 2012. Retrieved 13 September 2012.
  19. ^ "Queensland Police investigate three deaths linked to 'poison pill' ecstasy overdoses". news.com.au. 9 September 2012. Retrieved 30 September 2012.
  20. ^ "Den Bosch issues a warning for dangerous XTC-pills". nu.nl. Retrieved 12 June 2013.
  21. ^ . Archived from the original on 29 August 2013. Retrieved 30 August 2013.
  22. ^ "Naomi (16): dood door roze xtc-pil". 26 August 2013. from the original on 29 August 2013. Retrieved 26 August 2013.
  23. ^ . Archived from the original on 29 August 2013. Retrieved 26 August 2013.
  24. ^ "Man charged after ecstasy deaths". BBC News. 15 May 2018. from the original on 13 May 2018.
  25. ^ "Varning för livsfarlig ecstasy" (in Swedish). 2 January 2015. from the original on 5 January 2015. Retrieved 4 January 2015.
  26. ^ "Dublin student dies after taking PMMA tablets in nightclub". irishexaminer.com. 17 May 2015. from 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). from 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

  • Methyl-MA entry in PiHKAL
  • Methyl-MA entry in PiHKAL • info
  • Dutch article by TRIMBOS institute from 31-03-2011
  • Icelandic arictle by Mbl news(Mbl.is) from 30-04-2011

April 09, 2024
para, methoxy, methylamphetamine, also, known, pmma, mitsubishi, chemically, known, methyl, methoxy, methylamphetamine, pmda, listed, original, physical, name, stimulant, psychedelic, drug, closely, related, amphetamine, class, serotonergic, drug, para, methox. 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 2 In the early 2010s a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA 3 para Methoxy N methylamphetamineLegal statusLegal statusBR Class F2 Prohibited psychotropics 1 CA Schedule I DE Anlage I Authorized scientific use only UK Class A US Schedule 1IdentifiersIUPAC name 1 4 Methoxyphenyl N methylpropan 2 amineCAS Number22331 70 0 YPubChem CID90766ChemSpider81951UNII037U5SR9KLKEGGC22810 YCompTox Dashboard EPA DTXSID30874251ECHA InfoCard100 040 818Chemical and physical dataFormulaC 11H 17N OMolar mass179 263 g mol 13D model JSmol Interactive imageInteractive imageSMILES CC CC1 CC C C C1 OC NCC1 CC CC C1CC C NC OCInChI InChI 1S C11H17NO c1 9 12 2 8 10 4 6 11 13 3 7 5 10 h4 7 9 12H 8H2 1 3H3Key UGFMBZYKVQSQFX UHFFFAOYSA N verify Its effects in humans are reputedly similar to those of PMA but slightly more empathogenic in nature medical citation needed It has a reduced tendency to produce severe hyperthermia at 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 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 Contents 1 Recreational use 1 1 Deaths 2 Legal status 2 1 United States 2 2 United Kingdom 3 See also 4 References 5 External linksRecreational use edit nbsp Tablets of PMMA recovered by the U S Drug Enforcement AdministrationPMMA 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 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 a monoamine oxidase inhibitor MAOI if it is used in combination with MDMA or another MDMA like substance serotonin syndrome can result 9 PMMA can be detected with reagent testing kits Deaths edit This article may contain excessive or irrelevant examples Please help improve the article by adding descriptive text and removing less pertinent examples November 2019 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 10 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 11 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 12 13 14 15 16 17 In September 2012 the deaths of two men in County 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 of Sliedrecht 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 in Dublin Ireland after taking what is suspected to be PMMA 26 In April 2016 four young Argentines 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 27 Legal status editUnited 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 drug in the UK citation needed See also editpara Methoxyamphetamine PMA 2 Methoxymethamphetamine Methoxyphenamine 3 Methoxymethamphetamine MMMA 4 Fluoromethamphetamine 4 FMA 4 Methylmethamphetamine 4 MMA 4 Methoxymethcathinone bk PMMA VenlafaxineReferences edit Anvisa 24 July 2023 RDC Nº 804 Listas de Substancias Entorpecentes Psicotropicas 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 Diario Oficial da Uniao published 25 July 2023 Archived from the original on 27 August 2023 Retrieved 27 August 2023 Becker J Neis P Rohrich J Zorntlein S March 2003 A fatal paramethoxymethamphetamine intoxication Legal Medicine 5 5 Suppl 1 S138 41 doi 10 1016 s1344 6223 02 00096 2 PMID 12935573 Five B C deaths linked to lethal chemical PMMA Vancouver Sun 13 January 2012 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 PMID 9164566 S2CID 28758326 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 PMID 11420094 S2CID 41953749 Johansen SS Hansen AC Muller 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 PMID 12820749 S2CID 42519181 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 PMID 14616331 S2CID 28006785 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 PMID 18393753 S2CID 11987961 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 PMID 6103055 S2CID 42213032 PMMA deaths in Holland nu nl Retrieved 8 June 2011 Warning over ecstasy pills that raise overdose risk BBC News 16 December 2011 Archived from the original on 25 April 2012 Rare chemical found in fatal ecstasy The Province 15 January 2012 Archived from the original on 17 January 2012 Retrieved 12 January 2012 Overdose death investigated Nanton News 24 January 2012 Seized substances sent for testing after suspected overdose Calgary Herald Archived from the original on 27 January 2012 Retrieved 24 January 2012 Tainted ecstasy linked to five Calgary deaths could be from B C Vancouver Sun 12 January 2012 Archived from the original on 4 March 2013 Retrieved 12 January 2012 Authorities renew warning about street drugs The City of Calgary Newsroom Archived from the original on 15 January 2012 Retrieved 11 January 2012 Ecstasy laced with meth in overdose cases Archived from the original on 12 January 2012 Retrieved 12 January 2012 Dangerous drug linked to Kinsale deaths Irish Independent 13 September 2012 Archived from the original on 13 September 2012 Retrieved 13 September 2012 Queensland Police investigate three deaths linked to poison pill ecstasy overdoses news com au 9 September 2012 Retrieved 30 September 2012 Den Bosch issues a warning for dangerous XTC pills nu nl Retrieved 12 June 2013 Tiener overleden aan drugs Archived from the original on 29 August 2013 Retrieved 30 August 2013 Naomi 16 dood door roze xtc pil 26 August 2013 Archived from the original on 29 August 2013 Retrieved 26 August 2013 Waarschuwing dodelijke XTC in omloop Archived from the original on 29 August 2013 Retrieved 26 August 2013 Man charged after ecstasy deaths BBC News 15 May 2018 Archived from the original on 13 May 2018 Varning for livsfarlig ecstasy in Swedish 2 January 2015 Archived from the original on 5 January 2015 Retrieved 4 January 2015 Dublin student dies after taking PMMA tablets in nightclub irishexaminer com 17 May 2015 Archived from the original on 18 May 2015 Himitian Evangelina 17 April 2016 Conmocion por la muerte de cinco jovenes en una fiesta electronica La Nacion in Spanish Archived from the original on 19 April 2016 Schedules of Controlled Substances Placement of para Methoxymethamphetamine PMMA in Schedule I federalregister gov 25 June 2021 External links editMethyl MA entry in PiHKAL Methyl MA entry in PiHKAL info Dutch article by TRIMBOS institute from 31 03 2011 Icelandic arictle by Mbl news Mbl is from 30 04 2011 Retrieved from https en wikipedia org w index php title Para Methoxy N methylamphetamine amp oldid 1195358093, wikipedia, wiki, book, books, library,

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