Para-Methoxymethamphetamine

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para-Methoxymethamphetamine
4-Methoxymethamphetamine.svg
Clinical data
Other namesPMMA; p-Methoxymethamphetamine; para-Methoxy-N-methylamphetamine; 4-Methoxy-N-methylamphetamine; 4-MMA; Methyl-MA; 4-PMDA
Drug class Serotonin–norepinephrine releasing agent; Monoamine oxidase inhibitor
Legal status
Legal status
Identifiers
  • 1-(4-Methoxyphenyl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
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-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA), is a serotonergic drug of the amphetamine family related to para-methoxyamphetamine (PMA). It is the 4-methoxy analogue 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

PMMA is a serotonin–norepinephrine releasing agent (SNRA) [4] [5] [6] [7] as well as potent monoamine oxidase inhibitor (MAOI). [8] 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, [9] [10] but at higher dosages side effects and risk of death become similar to those of PMA. [11]

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

Pharmacodynamics

PMMA is a monoamine releasing agent (MRA). [4] [5] [6] [7] The drug's EC50 Tooltip half-maximal effective concentration values for induction of monoamine release in rat brain synaptosomes have been reported for the individual enantiomers of PMMA. [4] [5] [6] In the case of (S)-PMMA, they are 41 nM for serotonin, 147 nM for norepinephrine, and 1,000 nM for dopamine, whereas for (R)-PMMA, they are 134 nM for serotonin, >14,000 nM for norepinephrine, and 1,600 nM for dopamine. [4] [5] [6] Hence, PMMA appears to be a serotonin–norepinephrine releasing agent (SNRA) with weak effects on dopamine. [4] [5] [6] [7] The drug has been found to strongly release serotonin and to weakly release dopamine in the brain in rodents in vivo . [7]

In addition to its MRA activity, PMMA is a potent monoamine oxidase A (MAO-A) inhibitor. [8] Its IC50 Tooltip half-maximal inhibitory concentration for MAO-A inhibition has been reported to be 1,700 nM. [8] This is several-fold less potent than the related agents para-methoxyamphetamine (PMA) and 4-methylthioamphetamine (4-MTA). [8]

Monoamine release of PMMA Tooltip para-methoxymethamphetamine and related agents (EC50 Tooltip Half maximal effective concentration, nM)
Compound 5-HT Tooltip Serotonin NE Tooltip Norepinephrine DA Tooltip DopamineRef
d-Amphetamine 698–1,7656.6–7.25.8–24.8 [12] [13]
d-Methamphetamine 736–1,29212.3–13.88.5–24.5 [12] [14]
2-Methoxyamphetamine ND4731,478 [15]
3-Methoxyamphetamine ND58.0103 [15]
para-Methoxyamphetamine (PMA)ND166867 [15] [6]
PMMA Tooltip para-MethoxymethamphetamineNDNDNDND
  (S)-PMMA411471,000 [4] [5] [6]
  (R)-PMMA134>14,0001,600 [4] [5] [6]
4-Methylamphetamine (4-MA)53.422.244.1 [16] [17] [15]
4-Methylmethamphetamine (4-MMA)67.466.941.3 [18] [19]
para-Chloroamphetamine (PCA)28.323.5–26.242.2–68.5 [17] [15] [20] [21]
para-Chloromethamphetamine (PCMA)29.936.554.7 [20] [21]
Methedrone (4-MeO-MC)120–195111506–881 [22] [23] [24] [25] [26]
Mephedrone (4-MMC)118.3–12258–62.749.1–51 [14] [13] [23] [25] [26]
Notes: The smaller the value, the more strongly the drug releases the neurotransmitter. The assays were done in rat brain synaptosomes and human potencies may be different. See also Monoamine releasing agent § Activity profiles for a larger table with more compounds. Refs: [27] [28]

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. [29] [30] 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. [31]

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. [32] 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. [33]

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. [34] [35] [36] [37] [38] [39]

In September 2012, the deaths of two men in County Cork, Ireland, have been linked to PMMA overdoses. [40] In the same month, the death of a man in Queensland, Australia was attributed to PMMA. [41]

In June 2013 a PMMA-related death occurred in the Dutch city of 's-Hertogenbosch. [42] Two months later, In August 2013, another possibly PMMA-related death occurred in the nearby town of Sliedrecht. [43] [44] [45]

In January 2015 in the UK four people died, suspected of taking ecstasy containing PMMA. [46] In the same month, in Sweden, another man died from ecstasy laced with PMMA. [47]

In May 2015 a young woman died in Dublin, Ireland, after taking what is suspected to be PMMA. [48]

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. [49]

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. [50]

United Kingdom

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

See also

Related Research Articles

<span class="mw-page-title-main">Methcathinone</span> Psychoactive stimulant

Methcathinone is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational drug due to its potent stimulant and euphoric effects and is considered to be addictive, with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration. It is usually snorted, but can be smoked, injected, or taken orally.

<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">Etilamfetamine</span> Chemical compound

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

Naphthylaminopropane, also known as naphthylisopropylamine (NIPA), is an experimental drug that was under investigation for the treatment of alcohol and stimulant addiction.

<span class="mw-page-title-main">Norfenfluramine</span> Never-marketed drug of the amphetamine family

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<span class="mw-page-title-main">Monoamine releasing agent</span> Class of compounds

A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the neurotransmitters and hence enhanced signaling by those neurotransmitters. The monoamine neurotransmitters include serotonin, norepinephrine, and dopamine; MRAs can induce the release of one or more of these neurotransmitters.

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

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<span class="mw-page-title-main">2-Aminoindane</span> Chemical compound

2-Aminoindane (2-AI) is an aminoindane and research chemical with applications in neurologic disorders and psychotherapy that has also been sold as a designer drug. It acts as a selective substrate for NET and DAT.

<span class="mw-page-title-main">Dopamine releasing agent</span> Type of drug

A dopamine releasing agent (DRA) is a type of drug which induces the release of dopamine in the body and/or brain.

<span class="mw-page-title-main">Serotonin–dopamine releasing agent</span> Drug that releases serotonin and dopamine in the brain

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<span class="mw-page-title-main">4-Methylamphetamine</span> Stimulant and anorectic drug of the amphetamine class

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<span class="mw-page-title-main">4-Methylmethamphetamine</span> Stimulant and entactogen drug of the amphetamine class

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<span class="mw-page-title-main">Substituted cathinone</span> Class of chemical compounds

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<span class="mw-page-title-main">4,4'-Dimethylaminorex</span> Chemical compound

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<span class="mw-page-title-main">4-Methylcathinone</span> Stimulant designer drug

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

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<span class="mw-page-title-main">Naphthylmetrazine</span> Pharmaceutical 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.
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  3. ↑ "Five B.C. deaths linked to lethal chemical PMMA". Vancouver Sun. 10 January 2012.
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  31. ↑ 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.
  32. ↑ "PMMA deaths in Holland". nu.nl. Retrieved 8 June 2011.
  33. ↑ "Warning over ecstasy pills that raise overdose risk". BBC News. 16 December 2011. Archived from the original on 25 April 2012.
  34. ↑ "Rare chemical found in fatal ecstasy". The Province. 15 January 2012. Archived from the original on 17 January 2012. Retrieved 12 January 2012.
  35. ↑ "Overdose death investigated". Nanton News. 24 January 2012.
  36. ↑ "Seized substances sent for testing after suspected overdose". Calgary Herald. Archived from the original on 27 January 2012. Retrieved 24 January 2012.
  37. ↑ "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.
  38. ↑ "Authorities renew warning about street drugs". The City of Calgary Newsroom. Archived from the original on 15 January 2012. Retrieved 11 January 2012.
  39. ↑ "Ecstasy laced with meth in overdose cases". Archived from the original on 12 January 2012. Retrieved 12 January 2012.
  40. ↑ "Dangerous drug linked to Kinsale deaths". Irish Independent. 13 September 2012. Archived from the original on 13 September 2012. Retrieved 13 September 2012.
  41. ↑ "Queensland Police investigate three deaths linked to 'poison pill' ecstasy overdoses". news.com.au. 9 September 2012. Retrieved 30 September 2012.
  42. ↑ "Den Bosch issues a warning for dangerous XTC-pills". nu.nl. Retrieved 12 June 2013.
  43. ↑ "Tiener overleden aan drugs". Archived from the original on 29 August 2013. Retrieved 30 August 2013.
  44. ↑ "Naomi (16): dood door roze xtc-pil". 26 August 2013. Archived from the original on 29 August 2013. Retrieved 26 August 2013.
  45. ↑ "Waarschuwing: dodelijke 'XTC' in omloop". Archived from the original on 29 August 2013. Retrieved 26 August 2013.
  46. ↑ "Man charged after ecstasy deaths". BBC News. 15 May 2018. Archived from the original on 13 May 2018.
  47. ↑ "Varning för livsfarlig ecstasy" (in Swedish). 2 January 2015. Archived from the original on 5 January 2015. Retrieved 4 January 2015.
  48. ↑ "Dublin student dies after taking PMMA tablets in nightclub". irishexaminer.com. 17 May 2015. Archived from the original on 18 May 2015.
  49. ↑ 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.
  50. ↑ "Schedules of Controlled Substances: Placement of para-Methoxymethamphetamine (PMMA) in Schedule I". federalregister.gov. 25 June 2021.
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