para-Methoxy-N-methylamphetamine

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para-Methoxy-N-methylamphetamine
4-Methoxymethamphetamine.svg
Systematic (IUPAC) name
1-(4-methoxyphenyl)-N-methyl-propan-2-amine
Clinical data
Legal status
  • Controlled under Federal Analog Act
Identifiers
CAS number 3398-68-3 YesY
ATC code ?
PubChem CID 90766
ChemSpider 81951
Chemical data
Formula C11H17NO 
Mol. mass 179.259 g/mol
 YesY (what is this?)  (verify)

para-Methoxy-N-methylamphetamine (PMMA; Methyl-MA), also known as 4-methoxy-N-methylamphetamine (4-MMA), 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 ecstasy 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 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 alone, 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 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]

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. PMID 12935573. 
  2. ^ "Five B.C. deaths linked to lethal chemical PMMA". Vancouver Sun. January 13, 2012. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  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 PG, Ding GK, Nurmi LA (2008). "Fatal paramethoxy-amphetamine (PMA) poisoning in the Australian Capital Territory". Med. J. Aust. 188 (7): 426. PMID 18393753. 
  8. ^ Green, AL; El Hait, MA (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. January 15, 2012. Retrieved January 12, 2012. [dead link]
  12. ^ "Overdose death investigated". Nanton News. January 24, 2012. 
  13. ^ "Seized substances sent for testing after suspected overdose". Calgary Herald. Retrieved January 24, 2012. 
  14. ^ "Tainted ecstasy linked to five Calgary deaths could be from B.C.". Vancouver Sun. January 12, 2012. Retrieved January 12, 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. September 13, 2012. Retrieved September 13, 2012. 
  18. ^ "Queensland Police investigate three deaths linked to 'poison pill' ecstasy overdoses". news.com.au. September 9, 2012. Retrieved September 30, 2012. 
  19. ^ "Five young people die after taking super-strength 'Dr Death ecstasy'". Daily Mail UK. 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. 

External links[edit]