para-Methoxy-N-methylamphetamine

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para-Methoxy-N-methylamphetamine
4-Methoxymethamphetamine.svg
Legal status
Legal status
Identifiers
CAS Number 22331-70-0 YesY
PubChem (CID) 90766
ChemSpider 81951
UNII 037U5SR9KL YesY
ECHA InfoCard 100.020.242
Chemical and physical data
Formula C11H17NO
Molar mass 179.259 g/mol
3D model (Jmol) Interactive image
  (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[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.[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[edit]

In January 2011, the Norwegian Broadcasting Corporation reported that Norway had seen 12 deaths related to PMMA over the course of 6 months. In March 2011, Dutch media reported that there had been 4 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, 4 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.[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]

Legal status[edit]

United States[edit]

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[edit]

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[edit]

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

See also[edit]

References[edit]

  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. 
  11. ^ "Rare chemical found in fatal ecstasy". The Province. 15 January 2012. Retrieved 12 January 2012. [dead link]
  12. ^ "Overdose death investigated". Nanton News. 24 January 2012. 
  13. ^ "Seized substances sent for testing after suspected overdose". Calgary Herald. Retrieved 24 January 2012. 
  14. ^ "Tainted ecstasy linked to five Calgary deaths could be from B.C.". Vancouver Sun. 12 January 2012. Retrieved 12 January 2012. 
  15. ^ "Authorities renew warning about street drugs". The City of Calgary Newsroom. Retrieved 11 January 2012. 
  16. ^ "Ecstasy laced with meth in overdose cases". Retrieved 12 January 2012. 
  17. ^ "Dangerous drug linked to Kinsale deaths". Irish Independent. 13 September 2012. Retrieved 13 September 2012. 
  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. 
  20. ^ "Den Bosch issues a warning for dangerous XTC-pills". www.nu.nl. Retrieved 12 June 2013. 
  21. ^ "Tiener overleden aan drugs". Retrieved 30 August 2013. 
  22. ^ "Naomi (16): dood door roze xtc-pil". Retrieved 26 August 2013. 
  23. ^ "Waarschuwing: dodelijke 'XTC' in omloop". Retrieved 26 August 2013. 
  24. ^ http://m.bbc.co.uk/news/uk-england-30671300
  25. ^ "Varning för livsfarlig ecstasy" (in Swedish). Retrieved 4 January 2015. 
  26. ^ http://www.irishexaminer.com/breakingnews/ireland/dublin-student-dies-after-taking-pmma-tablets-in-nightclub-677531.html
  27. ^ http://www.lanacion.com.ar/1890177-conmocion-por-la-muerte-de-cinco-jovenes-en-una-fiesta-electronica.  Missing or empty |title= (help)
  28. ^ "21 CFR — Schedules of Controlled Substances §1308.11 Schedule I". 
  29. ^ "Florida Statutes – Chapter 893 – Drug Abuse Prevention and Control". 

External links[edit]