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para-Methoxy-N-methylamphetamine

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics) CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule 1
Identifiers
IUPAC name 1-(4-Methoxyphenyl)-N-methylpropan-2-amine
CAS Number	22331-70-0
PubChem CID	90766
ChemSpider	81951
UNII	037U5SR9KL
KEGG	C22810
CompTox Dashboard (EPA)	DTXSID30874251
ECHA InfoCard	100.040.818
Chemical and physical data
Formula	C11H17NO
Molar mass	179.263 g·mol
3D model (JSmol)	Interactive image Interactive image
SMILES CC(CC1=CC=C(C=C1)OC)NC C1=CC(=CC=C1CC(C)NC)OC
InChI InChI=1S/C11H17NO/c1-9(12-2)8-10-4-6-11(13-3)7-5-10/h4-7,9,12H,8H2,1-3H3 Key:UGFMBZYKVQSQFX-UHFFFAOYSA-N
(verify)

para-Methoxy-N-methylamphetamine (also known as PMMA, Red Mitsubishi), chemically known as methyl-MA, 4-methoxy-N-methylamphetamine, and 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 become 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.

Pharmacology

PMMA is a monoamine oxidase A (MAO-A) inhibitor. Its IC₅₀Tooltip half-maximal inhibitory concentration for MAO-A inhibition has been reported to be 1,700 nM.

Recreational use

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 reagent testing kits.

Deaths

This article may contain excessive or irrelevant examples. Please help improve the article by adding descriptive text and removing less pertinent examples. (November 2019)

In January 2011, the Norwegian Broadcasting Corporation reported that Norway had seen 12 deaths related to PMMA over the course of six months. In March 2011, Dutch media reported that there had been four 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 2011, four deaths were recorded in Scotland as a result of ecstasy tablets which also contained PMMA.

In January 2012, a number of ecstasy-related deaths in Canada in the previous year were linked to PMMA overdoses. In the single year, approximately 45 exposures occurred, resulting in 21 deaths. Cases were centred primarily in Calgary and Vancouver.

In September 2012, the deaths of two men in County Cork, Ireland, have been linked to PMMA overdoses. In the same month, the death of a man in Queensland, Australia was attributed to PMMA.

In June 2013 a PMMA-related death occurred in the Dutch city of 's-Hertogenbosch. Two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town of Sliedrecht.

In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA. In the same month, in Sweden, another man died from ecstasy laced with PMMA.

In May 2015 a young woman died in Dublin, Ireland, after taking what is suspected to be PMMA.

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.

Legal status

United States

On June 25, 2021 the DEA finalized a rule placing PMMA on the Controlled Substance Act federal Schedule as a Schedule I substance effective July 26, 2021.

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

1. Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
2. Becker J, Neis P, Röhrich J, Zörntlein S (March 2003). "A fatal paramethoxymethamphetamine intoxication". Legal Medicine. 5. 5 (Suppl 1): S138-41. doi:10.1016/s1344-6223(02)00096-2. PMID 12935573.
3. "Five B.C. deaths linked to lethal chemical PMMA". Vancouver Sun. 10 January 2012.
4. 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. S2CID 28758326.
5. 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. S2CID 41953749.
6. 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. S2CID 42519181.
7. ^ Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK (2019). "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol. 10: 1590. doi:10.3389/fphar.2019.01590. PMC 6989591. PMID 32038257.
8. Refstad S (November 2003). "Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects". Acta Anaesthesiologica Scandinavica. 47 (10): 1298–9. doi:10.1046/j.1399-6576.2003.00245.x. PMID 14616331. S2CID 28006785.
9. Lamberth PG, Ding GK, Nurmi LA (April 2008). "Fatal paramethoxy-amphetamine (PMA) poisoning in the Australian Capital Territory". The Medical Journal of Australia. 188 (7): 426. doi:10.5694/j.1326-5377.2008.tb01695.x. PMID 18393753. S2CID 11987961.
10. Green AL, El Hait MA (April 1980). "p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo". The Journal of Pharmacy and Pharmacology. 32 (4): 262–6. doi:10.1111/j.2042-7158.1980.tb12909.x. PMID 6103055. S2CID 42213032.
11. "PMMA deaths in Holland". nu.nl. Retrieved 8 June 2011.
12. "Warning over ecstasy pills that raise overdose risk". BBC News. 16 December 2011. Archived from the original on 25 April 2012.
13. "Rare chemical found in fatal ecstasy". The Province. 15 January 2012. Archived from the original on 17 January 2012. Retrieved 12 January 2012.
14. "Overdose death investigated". Nanton News. 24 January 2012.
15. "Seized substances sent for testing after suspected overdose". Calgary Herald. Archived from the original on 27 January 2012. Retrieved 24 January 2012.
16. "Tainted ecstasy linked to five Calgary deaths could be from B.C." Vancouver Sun. 12 January 2012. Archived from the original on 4 March 2013. Retrieved 12 January 2012.
17. "Authorities renew warning about street drugs". The City of Calgary Newsroom. Archived from the original on 15 January 2012. Retrieved 11 January 2012.
18. "Ecstasy laced with meth in overdose cases". Archived from the original on 12 January 2012. Retrieved 12 January 2012.
19. "Dangerous drug linked to Kinsale deaths". Irish Independent. 13 September 2012. Archived from the original on 13 September 2012. Retrieved 13 September 2012.
20. "Queensland Police investigate three deaths linked to 'poison pill' ecstasy overdoses". news.com.au. 9 September 2012. Retrieved 30 September 2012.
21. "Den Bosch issues a warning for dangerous XTC-pills". nu.nl. Retrieved 12 June 2013.
22. "Tiener overleden aan drugs". Archived from the original on 29 August 2013. Retrieved 30 August 2013.
23. "Naomi (16): dood door roze xtc-pil". 26 August 2013. Archived from the original on 29 August 2013. Retrieved 26 August 2013.
24. "Waarschuwing: dodelijke 'XTC' in omloop". Archived from the original on 29 August 2013. Retrieved 26 August 2013.
25. "Man charged after ecstasy deaths". BBC News. 15 May 2018. Archived from the original on 13 May 2018.
26. "Varning för livsfarlig ecstasy" (in Swedish). 2 January 2015. Archived from the original on 5 January 2015. Retrieved 4 January 2015.
27. "Dublin student dies after taking PMMA tablets in nightclub". irishexaminer.com. 17 May 2015. Archived from the original on 18 May 2015.
28. Himitian, Evangelina (17 April 2016). "Conmoción por la muerte de cinco jóvenes en una fiesta electrónica". La Nación (in Spanish). Archived from the original on 19 April 2016.
29. "Schedules of Controlled Substances: Placement of para-Methoxymethamphetamine (PMMA) in Schedule I". federalregister.gov. 25 June 2021.

External links

• 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

• Monoamine oxidase inhibitors
• 4-Methoxyphenyl compounds
• Designer drugs
• Serotonin releasing agents
• Methamphetamines