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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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.040.818 Edit this at Wikidata
Chemical and physical data
FormulaC11H17NO
Molar mass179.259 g/mol g·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 as PMMA, Red Mitsubishi), chemically known as methyl-MA, 4-methoxy-N-methylamphetamine, 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.[medical citation needed] It has a reduced tendency to produce severe hyperthermia at low dosages,[3][4] but at higher dosages side effects and risk of death becomes 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 pill 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 December 2012 and January 2013, several deaths were linked to PMMA in the UK.[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]

United States

PMMA is not scheduled at the federal level in the United States,[28] but could be considered an analog (of PMA), in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analog Act.

Florida

PMMA is a Schedule I controlled substance in the state of Florida, listed as "4-methoxymethamphetamine", making it illegal to buy, sell, or possess in Florida.[29]

United Kingdom

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

See also

References

  1. ^ Becker, J.; Neis, P.; Röhrich, J.; Zörntlein, S. (2003). "A fatal paramethoxymethamphetamine intoxication". Legal Medicine (Tokyo, Japan). 5. Suppl. 1: S138–41. 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.
  3. ^ Glennon, R. A.; 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.
  4. ^ Rangisetty, J. B.; Bondarev, M. L.; Chang-Fong, J.; Young, R.; Glennon, R. A. (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.
  5. ^ Johansen, S. S.; Hansen, A. C.; Müller, I. B.; Lundemose, J. B.; Franzmann, M. B. (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.
  6. ^ Refstad, S. (2003). "Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects". Acta Anaesthesiol. Scand. 47 (10): 1298–9. doi:10.1046/j.1399-6576.2003.00245.x. PMID 14616331.
  7. ^ Lamberth, P. G.; Ding, G. K.; Nurmi, L. A. (2008). "Fatal para-methoxy-amphetamine (PMA) poisoning in the Australian Capital Territory". Med. J. Aust. 188 (7): 426. PMID 18393753.
  8. ^ Green, A. L.; El Hait, M. A. (1980). "p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo". J. Pharm. Pharmacol. 32 (4): 262–266. doi:10.1111/j.2042-7158.1980.tb12909.x. PMID 6103055.
  9. ^ "PMMA deaths in Holland". www.nu.nl. Retrieved 8 June 2011.
  10. ^ "Warning over ecstasy pills that raise overdose risk". BBC News. 16 December 2011. Archived from the original on 25 April 2012. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  11. ^ "Rare chemical found in fatal ecstasy". The Province. 15 January 2012. Archived from the original on 17 January 2012. Retrieved 12 January 2012. {{cite web}}: Unknown parameter |dead-url= ignored (|url-status= suggested) (help)
  12. ^ "Overdose death investigated". Nanton News. 24 January 2012.
  13. ^ "Seized substances sent for testing after suspected overdose". Calgary Herald. Archived from the original on 27 January 2012. Retrieved 24 January 2012. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  14. ^ "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. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  15. ^ "Authorities renew warning about street drugs". The City of Calgary Newsroom. Archived from the original on 15 January 2012. Retrieved 11 January 2012. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  16. ^ "Ecstasy laced with meth in overdose cases". Archived from the original on 12 January 2012. Retrieved 12 January 2012. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  17. ^ "Dangerous drug linked to Kinsale deaths". Irish Independent. 13 September 2012. Archived from the original on 13 September 2012. Retrieved 13 September 2012. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  18. ^ "Queensland Police investigate three deaths linked to 'poison pill' ecstasy overdoses". news.com.au. 9 September 2012. Retrieved 30 September 2012.
  19. ^ "Five young people die after taking super-strength 'Dr Death ecstasy'". Daily Mail. 23 January 2013. Archived from the original on 20 April 2013. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  20. ^ "Den Bosch issues a warning for dangerous XTC-pills". www.nu.nl. Retrieved 12 June 2013.
  21. ^ "Tiener overleden aan drugs". Archived from the original on 29 August 2013. Retrieved 30 August 2013. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  22. ^ "Naomi (16): dood door roze xtc-pil". Archived from the original on 29 August 2013. Retrieved 26 August 2013. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  23. ^ "Waarschuwing: dodelijke 'XTC' in omloop". Archived from the original on 29 August 2013. Retrieved 26 August 2013. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  24. ^ "Man charged after ecstasy deaths". 15 May 2018. Archived from the original on 13 May 2018 – via www.bbc.co.uk. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  25. ^ "Varning för livsfarlig ecstasy" (in Swedish). Archived from the original on 5 January 2015. Retrieved 4 January 2015. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  26. ^ "Dublin student dies after taking PMMA tablets in nightclub". irishexaminer.com. 17 May 2015. Archived from the original on 18 May 2015. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  27. ^ "Conmoción por la muerte de cinco jóvenes en una fiesta electrónica" (in Spanish). 17 April 2016. Archived from the original on 19 April 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  28. ^ "21 CFR — Schedules of Controlled Substances §1308.11 Schedule I". Archived from the original on 27 August 2009. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  29. ^ "Florida Statutes – Chapter 893 – Drug Abuse Prevention and Control". Archived from the original on 14 March 2018. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)

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