|Chemical and physical data|
|Molar mass||179.259 g/mol|
|3D model (Jmol)||Interactive image|
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. In the early 2010s, a number of deaths in users of the drug MDMA 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, but at higher dosages side effects and risk of death becomes similar to those of PMA.
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.
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. 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.
PMMA can be detected with pill testing kits.
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. In April 2011, Icelandic media reported the death of a young woman that may have been connected to PMMA.
In January 2012, a number of ecstasy-related deaths in Canada in the previous year were linked to PMMA overdoses.
In May 2015 a young woman died in Dublin, Ireland, after taking what is suspected to be PMMA.
PMMA is not scheduled at the federal level in the United States, 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.
PMMA is controlled as a Schedule 1, Class A drug in the UK.
- para-Methoxyamphetamine (PMA)
- 2-Methoxymethamphetamine (Methoxyphenamine)
- 3-Methoxymethamphetamine (MMMA)
- 4-Fluoromethamphetamine (4-FMA)
- 4-Methylmethamphetamine (4-MMA)
- 4-Methoxymethcathinone (bk-PMMA)
- 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.
- "Five B.C. deaths linked to lethal chemical PMMA". Vancouver Sun. 13 January 2012.
- 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.
- 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.
- 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.
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- 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.
- 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.
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- "Overdose death investigated". Nanton News. 24 January 2012.
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- http://www.lanacion.com.ar/1890177-conmocion-por-la-muerte-de-cinco-jovenes-en-una-fiesta-electronica. Missing or empty
- "21 CFR — Schedules of Controlled Substances §1308.11 Schedule I".
- "Florida Statutes – Chapter 893 – Drug Abuse Prevention and Control".
- Methyl-MA entry in PiHKAL
- Methyl-MA entry in PiHKAL • info
- Dutch article by TRIMBOS institute from 31-03-2011
- Icelandic arictle by Mbl news(Mbl.is) from 30-04-2011