para-Methoxy-N-methylamphetamine
![]() |
|
Systematic (IUPAC) name | |
---|---|
1-(4-Methoxyphenyl)-N-methyl-propan-2-amine
|
|
Clinical data | |
Legal status |
|
Identifiers | |
CAS Number | 3398-68-3 ![]() |
PubChem | CID: 90766 |
ChemSpider | 81951 |
UNII | 037U5SR9KL ![]() |
Chemical data | |
Formula | C11H17NO |
Molecular mass | 179.259 g/mol |
|
|
|
|
(verify) |
para-Methoxy-N-methylamphetamine (also known as PMMA, Red Mitsubishi), chemically known as methyl-MA, 4-methoxy-N-methylamphetamine, or 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 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.
Contents
Recreational use
![](/w/images/thumb/7/76/PMMA_tablets.jpg/200px-PMMA_tablets.jpg)
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 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 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 Argentinians 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
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
See also
- para-Methoxyamphetamine (PMA)
- 2-Methoxymethamphetamine (Methoxyphenamine)
- 3-Methoxymethamphetamine (MMMA)
- 4-Fluoromethamphetamine (4-FMA)
- 4-Methylmethamphetamine (4-MMA)
- 4-Methoxymethcathinone (bk-PMMA)
- Venlafaxine
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.[dead link]
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ http://m.bbc.co.uk/news/uk-england-30671300
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ http://www.irishexaminer.com/breakingnews/ireland/dublin-student-dies-after-taking-pmma-tablets-in-nightclub-677531.html
- ↑ http://www.lanacion.com.ar/1890177-conmocion-por-la-muerte-de-cinco-jovenes-en-una-fiesta-electronica
- ↑ 21 CFR — SCHEDULES OF CONTROLLED SUBSTANCES §1308.11 Schedule I.
- ↑ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
External links
- Articles with dead external links from June 2012
- Drugs with non-standard legal status
- Chemical articles having calculated molecular weight overwritten
- Chemical articles with unknown parameter in Infobox drug
- Infobox drug articles without a structure image
- Articles without EBI source
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Drugboxes with an unspecified ATC code
- Articles with unsourced statements from January 2015
- Articles with unsourced statements from February 2012
- Use dmy dates from May 2011
- Monoamine oxidase inhibitors
- Phenol ethers
- Designer drugs
- Serotonin releasing agents
- Methamphetamines