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-Methoxymethamphetamine

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

para-Methoxymethamphetamine (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.

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,[2][3] but at higher dosages side effects and risk of death becomes similar to those of PMA.[4]

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

Recreational Usage

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.[5][6] 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.[7]

Deaths

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 of 2010.[8] In April 2011, Icelandic media reported the death of a young woman that may have been connected to PMMA.[citation needed]

In January 2012, a number of ecstasy-related deaths in Canada in the previous year were linked to PMMA overdoses.[9][10][11][12][13] [14]

See also

External links

References

  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. ^ 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. 
  3. ^ 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. 
  4. ^ 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. PMID 12820749. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ J Pharm Pharmacol. 1980 Apr;32(4):262-6.
  8. ^ "PMMA deaths in Holland". www.nu.nl. http://translate.google.com/translate?js=n&prev=_t&hl=nl&ie=UTF-8&layout=2&eotf=1&sl=nl&tl=en&u=http%3A%2F%2Fwww.nu.nl%2Fbinnenland%2F2535695%2Fpinkpopgangers-moeten-uitkijken-met-xtc.html. Retrieved 8 June 2011. 
  9. ^ http://www.theprovince.com/life/Rare+chemical+found+fatal+ecstasy/5998482/story.html, The Province, January 15, 2012, Retrieved January 12, 2012.
  10. ^ http://www.nantonnews.com/ArticleDisplay.aspx?e=3446181 Nanton News, Overdose death investigated January 24, 2012.
  11. ^ http://www.calgaryherald.com/news/alberta/Update+Seized+substances+sent+testing+after+suspected+overdose+SAIT/6037966/story.html Retrieved January 24, 2012.
  12. ^ Tainted ecstasy linked to five Calgary deaths could be from B.C., http://www.vancouversun.com/touch/story.html?id=5980841, Vancouver Sun, January 12, 2012, Retrieved January 12, 2012.
  13. ^ "Authorities renew warning about street drugs". The City of Calgary Newsroom. http://newsroom.calgary.ca/pr/calgary/authorities-renew-warning-about-221684.aspx. Retrieved 11 January 2012. 
  14. ^ "Ecstasy laced with meth in overdose cases". http://www.cbc.ca/news/canada/calgary/story/2012/01/11/calgary-ecstasy-meth-deaths.html. Retrieved 12 January 2012. 

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