Para-Methoxy-N-methylamphetamine

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para-Methoxy-N-methylamphetamine
4-Methoxymethamphetamine.svg
Legal status
Legal status
Identifiers
  • 1-(4-Methoxyphenyl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
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ECHA InfoCard 100.040.818 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H17NO
Molar mass 179.263 g·mol−1
3D model (JSmol)
  • CC(CC1=CC=C(C=C1)OC)NC

  • C1=CC(=CC=C1CC(C)NC)OC
  • 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. [2] In the early 2010s, a number of deaths in users of the drug MDMA were linked to misrepresented tablets and capsules of PMMA. [3]

Contents

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, [4] [5] but at higher dosages side effects and risk of death become similar to those of PMA. [6]

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. [7] Its IC50 Tooltip half-maximal inhibitory concentration for MAO-A inhibition has been reported to be 1,700 nM. [7]

Recreational use

Tablets of PMMA recovered by the U.S. Drug Enforcement Administration PMMA tablets.jpg
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. [8] [9] 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. [10]

PMMA can be detected with reagent testing kits.

Deaths

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

In 2011, four deaths were recorded in Scotland as a result of ecstasy tablets which also contained PMMA. [12]

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. [13] [14] [15] [16] [17] [18]

In September 2012, the deaths of two men in County Cork, Ireland, have been linked to PMMA overdoses. [19] In the same month, the death of a man in Queensland, Australia was attributed to PMMA. [20]

In June 2013 a PMMA-related death occurred in the Dutch city of 's-Hertogenbosch. [21] Two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town of Sliedrecht. [22] [23] [24]

In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA. [25] In the same month, in Sweden, another man died from ecstasy laced with PMMA. [26]

In May 2015 a young woman died in Dublin, Ireland, after taking what is suspected to be PMMA. [27]

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. [28]

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. [29]

United Kingdom

PMMA is controlled as a Schedule 1, Class A drug in the UK.[ citation needed ]

See also

Related Research Articles

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<i>PiHKAL</i> 1991 book by Alexander Shulgin and Ann Shulgin

PiHKAL: A Chemical Love Story is a book by Alexander Shulgin and Ann Shulgin, published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title, PiHKAL, is an acronym that stands for "Phenethylamines I Have Known and Loved".

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

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<span class="mw-page-title-main">5-MeO-AMT</span> Chemical compound

5-MeO-αMT, or 5-methoxy-α-methyltryptamine, also known as α,O-dimethylserotonin (Alpha-O), is a serotonergic psychedelic of the tryptamine family. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.

α-Ethyltryptamine Chemical compound

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<i>para</i>-Methoxyamphetamine Chemical compound

para-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogen effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.

<span class="mw-page-title-main">Harmala alkaloid</span> Group of chemical compounds

Harmala alkaloids are several alkaloids that act as monoamine oxidase inhibitors (MAOIs). These alkaloids are found in the seeds of Peganum harmala, as well as Banisteriopsis caapi (ayahuasca), leaves of tobacco and coffee beans. The alkaloids include harmine, harmaline, harmalol, and their derivatives, which have similar chemical structures, hence the name "harmala alkaloids". These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. Harmine, once known as telepathine and banisterine, is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi and P. harmala. Dr. Alexander Shulgin has suggested that harmine may be a breakdown product of harmaline. Harmine and harmaline are reversible inhibitors of monoamine oxidase A (RIMAs). They can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine.

<span class="mw-page-title-main">MBDB</span> Chemical compound

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<span class="mw-page-title-main">4-Methylthioamphetamine</span> Chemical compound

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<span class="mw-page-title-main">1,3-Benzodioxolylbutanamine</span> Enactogenic drug of the phenethylamine class

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<span class="mw-page-title-main">MDAI</span> Chemical compound

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<span class="mw-page-title-main">3-Methoxy-4-methylamphetamine</span> Entactogen and psychedelic drug of the phenethylamine and amphetamine classes

3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s (decade).

<span class="mw-page-title-main">3-Methoxyamphetamine</span> Stimulant drug of the amphetamine class

meta-Methoxyamphetamine (MMA), also known as 3-methoxyamphetamine (3-MA), is a stimulant drug from the amphetamine family. It has similar effects in animal drug discrimination tests to the more widely known derivative 4-methoxyamphetamine (PMA), although with a slightly different ratio of monoamine release, being a combined serotonin, dopamine, and norepinephrine releasing agent rather than a fairly selective serotonin releaser like PMA. 3-Methoxyamphetamine has similarly appeared on the illicit market as a designer drug alternative to MDMA, although far more rarely than its infamous positional isomer. It produces gepefrine, a cardiac stimulant, as one of its major metabolites.

<span class="mw-page-title-main">3-Methoxymethamphetamine</span> Chemical compound

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Substituted amphetamines, or simply amphetamines, are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

<span class="mw-page-title-main">5-Chloro-αMT</span> Chemical compound

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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. 1 2 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.
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