Biology:Para-Methoxyamphetamine

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Short description: Chemical compound


Not to be confused with 4-methylamphetamine or 4-MA steroid.

PMA
Clinical data
Other namespara-Methoxyamphetamine; p-Methoxyamphetamine; PMA; 4-Methoxyamphetamine; 4-MA; 4-MeO-A; 4-OMe-PIA
Routes of
administration		Oral[1][2]
Drug classSerotonin releasing agent; Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen; Monoamine oxidase inhibitor
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action"Short"[1][2]
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 g·mol−1
3D model (JSmol)
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para-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects.[3][1][4] Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogenic effects,[5] and behaves more like an antidepressant in comparison,[6] though it does have some psychedelic properties.[7][8]

PMA has been found in black market tablets sold as MDMA (ecstasy)[9][10][11][12] although its effects are markedly different compared to those of MDMA. The consequences of such deception have often included hospitalization and death for unwitting users. PMA is commonly synthesized from anethole, the essential oil of anise and fennel, mainly because the starting material for MDMA and MDA, safrole (a major component of the essential oil of sassafras), has become less available due to increasing government controls, causing illicit drug manufacturers to make PMA as an alternative.[13]

Use and effects

According to Alexander Shulgin in PiHKAL (Phenethylamines I Have Known and Loved), the effects of PMA at doses of 50 to 80 mg orally included hypertension, diethyltryptamine (DET)-reminiscent effects, distinct after-images, and some paresthesia, "intoxication" or alcohol-like intoxication, and no psychedelic effects.[1][2] In clinical studies, PMA produced excitation, other central effects, and sympathomimetic effects, but similarly no psychotomimetic effects.[2]

Adverse effects

PMA has been associated with numerous adverse reactions including death.[14][15] Effects of PMA ingestion include many effects of the hallucinogenic amphetamines including accelerated and irregular heartbeat, blurred vision, and a strong feeling of intoxication that is often unpleasant. At high doses unpleasant effects such as nausea and vomiting, severe hyperthermia and hallucinations may occur. The effects of PMA also seem to be much more unpredictable and variable between individuals than those of MDMA, and sensitive individuals may die from a dose of PMA by which a less susceptible person might only be mildly affected.[16] While PMA alone may cause significant toxicity, the combination of PMA with MDMA has a synergistic effect that seems to be particularly hazardous.[17] Since PMA has a slow onset of effects, several deaths have occurred where individuals have taken a pill containing PMA, followed by a pill containing MDMA some time afterwards due to thinking that the first pill was not active.[18]

Overdose

PMA overdose can be a serious medical emergency that may occur at only slightly above the usual recreational dose range, especially if PMA is mixed with other stimulant drugs such as cocaine or MDMA. Characteristic symptoms are pronounced hyperthermia, tachycardia, and hypertension, along with agitation, confusion, and convulsions. PMA overdose also tends to cause hypoglycemia and hyperkalemia, which can help to distinguish it from MDMA overdose. Complications can sometimes include more serious symptoms such as rhabdomyolysis and cerebral hemorrhage, requiring emergency surgery. There is no specific antidote, so treatment is symptomatic, and usually includes both external cooling, and internal cooling via IV infusion of cooled saline. Benzodiazepines are used initially to control convulsions, with stronger anticonvulsants such as phenytoin or thiopental used if convulsions continue. Blood pressure can be lowered either with a combination of alpha blockers and beta blockers (or a mixed alpha/beta blocker), or with other drugs such as nifedipine or nitroprusside. Serotonin antagonists and dantrolene may be used as required. Despite the seriousness of the condition, the majority of patients survive if treatment is given in time, however, patients with a core body temperature over 40 °C at presentation tend to have a poor prognosis.[19]

Pharmacology

Pharmacodynamics

Actions

Monoamine release of PMA and related agents (EC50, nM)
Compound 5-HT NE DA Ref
d-Amphetamine 698–1,765 6.6–7.2 5.8–24.8 [20][21]
d-Methamphetamine 736–1,292 12.3–13.8 8.5–24.5 [20][22]
2-Methoxyamphetamine ND 473 1,478 [23]
3-Methoxyamphetamine ND 58.0 103 [23]
para-Methoxyamphetamine (PMA) ND 166 867 [23][24]
PMMA ND ND ND ND
  (S)-PMMA 41 147 1,000 [25][26][24]
  (R)-PMMA 134 >14,000 1,600 [25][26][24]
4-Methylamphetamine (4-MA) 53.4 22.2 44.1 [27][28][23]
4-Methylmethamphetamine (4-MMA) 67.4 66.9 41.3 [29][30]
para-Chloroamphetamine (PCA) 28.3 23.5–26.2 42.2–68.5 [28][23][31][32]
para-Chloromethamphetamine (PCMA) 29.9 36.5 54.7 [31][32]
Methedrone (4-MeO-MC) 120–195 111 506–881 [33][34][35][36][37]
Mephedrone (4-MMC) 118.3–122 58–62.7 49.1–51 [22][21][34][36][37]
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: [38][39]

PMA acts as a selective serotonin releasing agent (SSRA) with weak effects on dopamine and norepinephrine transporters.[40][41][42][43] Its EC50 values for induction of monoamine release are 166 nM for dopamine and 867 nM for norepinephrine in rat brain synaptosomes, whereas serotonin was not reported.[23][24] The drug has been found to robustly increase brain serotonin levels and to weakly increase brain dopamine levels in rodents in vivo.[44] Relative to MDMA, PMA appears to be considerably less effective as a releaser of serotonin, with properties more akin to a serotonin reuptake inhibitor in comparison.[45]

PMA has also been shown to act as a potent monoamine oxidase inhibitor (MAOI), specifically as a reversible inhibitor of the enzyme monoamine oxidase A (MAO-A) with no significant effects on monoamine oxidase B (MAO-B).[46][47] The IC50 of PMA for MAO-A inhibition has been reported to be 300 to 600 nM.[48]

PMA shows very low affinities for the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors.[43] Its affinities (Ki) for these receptors have been reported to be >20,000 nM, 11,200 nM, and >13,000 nM, respectively.[43] In another earlier study, PMA similarly showed very weak affinity for serotonin receptors, including the serotonin 5-HT1 and 5-HT2 receptors (Ki = 79,400 nM and 33,600 nM, respectively).[49][50] On the other hand, PMA shows much higher affinities for the mouse and rat trace amine-associated receptor 1 (TAAR1).[43]

Effects

PMA fails to substitute for the psychedelic drug DOM in rodent drug discrimination tests.[51] It only partially substituted for the psychostimulant amphetamine in such tests.[2][25][52] The drug did not substitute for MDMA in rodents, suggesting lack of entactogenic effects.[25] PMA evokes robust hyperthermia in rodents while producing only modest hyperlocomotion and serotonergic neurotoxicity, substantially lower than that caused by MDMA, and only at very high doses.[41][42][45] Accordingly, it is not self-administered by rodents unlike amphetamine and MDMA.[5]

It appears that PMA elevates body temperatures dramatically; the cause of this property is suspected to be related to its ability to inhibit MAO-A and at the same time releasing large amounts of serotonin, effectively causing serotonin syndrome.[45][47] Amphetamines, especially serotonergic analogues such as MDMA, are strongly contraindicated to take with MAOIs. Many amphetamines and adrenergic compounds raise body temperatures, whereas some tend to produce more euphoric activity or peripheral vasoconstriction, and may tend to favor one effect over another. It appears that PMA activates the hypothalamus much more strongly than MDMA and other drugs like ephedrine, thereby causing rapid increases in body temperature (which is the major cause of death in PMA mortalities).[53][54][55] Many people taking PMA try to get rid of the heat by taking off their clothes, taking cold showers or wrapping themselves in wet towels, and even sometimes by shaving off their hair.[56]

Chemistry

Synthesis

The chemical synthesis of PMA has been described.[1][2]

Analogues

Analogues of PMA include para-methoxy-N-methylamphetamine (PMMA), para-methoxy-N-ethylamphetamine (PMEA), 4-ethoxyamphetamine (4-ETA), 4-methylthioamphetamine (4-MTA), 4-methylamphetamine (4-MA), 4-hydroxyamphetamine, para-chloroamphetamine (PCA), 2-methoxyamphetamine (OMA), 3-methoxyamphetamine (MMA), 3-methoxy-4-methylamphetamine (MMA), 3,4-dimethoxyamphetamine (3,4-DMA), and 1-aminomethyl-5-methoxyindane (AMMI), among others.[1][2] Anisomycin contains PMA within its chemical structure.

History

PMA was first described in the scientific literature by T. Patrick and colleagues by 1946.[57] It first came into circulation as a recreational drug in the early 1970s, where it was used intentionally as a substitute for the psychedelic drug LSD.[1] The drug went by the street names of "Chicken Powder" and "Chicken Yellow" and was found to be the cause of a number of drug overdose deaths (the doses taken being in the range of hundreds of milligrams) in the United States and Canada from that time.[58] Between 1974 and the mid-1990s, there appear to have been no known fatalities from PMA.[59]

Several deaths reported as MDMA-induced in Australia in the mid-1990s are now considered to have been caused by PMA, the users unaware that they were ingesting PMA and not MDMA as they had intended.[12] There have been a number of PMA-induced deaths around the world since then.[60][61]

In July 2013, seven deaths in Scotland were linked to tablets containing PMA that had been mis-sold as ecstasy and which had the Rolex crown logo on them.[10] Several deaths in Northern Ireland, Particularly East Belfast, were also linked to "Green Rolex" pills during that month.[62]

In 2014, 2015, and early 2016, PMA sold as ecstasy was the cause of more deaths in the United States, United Kingdom, Netherlands, and Argentina. The pills containing the drug were reported to be red triangular tablets with a "Superman" logo.[11][63][64][65]

The Red Ferarri pills are a new press of the Superman logo tablets that were reported to be found in Germany and Norway from 2016 to 2017.[66]

Society and culture

International

PMA is a Schedule I drug under the Convention on Psychotropic Substances.[67]

Australia

PMA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[68] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[68]

Canada

PMA is a Schedule I controlled substance in Canada.[69]

Finland

Substance is scheduled in decree of the substances, preparations and plants considered to be narcotic drugs.[70][71]

Germany

PMA is part of the Appendix 1 of the Betäubungsmittelgesetz. Therefore, owning and distribution of PMA is illegal.

Netherlands

On 13 June 2012 Edith Schippers, Dutch Minister of Health, Welfare and Sport, revoked the legality of PMA in the Netherlands after five deaths were reported in that year.[72]

United Kingdom

PMA is a Class A drug in the UK.[73]

United States

PMA is classified as a Schedule I hallucinogen under the Controlled Substances Act in the United States.[74]

Economics

Distribution

Because PMA is given out through the same venues and distribution channels that MDMA tablets are, the risk of being severely injured, hospitalized or even dying from use of ecstasy increases significantly when a batch of ecstasy pills containing PMA starts to be sold in a particular area.[75] PMA pills could be a variety of colours or imprints, and there is no way of knowing just from the appearance of a pill what drug(s) it might contain.[76][77] Notable batches of pills containing PMA have included Louis Vuitton,[78] Mitsubishi Turbo, Blue Transformers, Red/Blue Mitsubishi and Yellow Euro pills. Also PMA has been found in powder form.[79]

Analogues

Four analogues of PMA have been reported to be sold on the black market, including PMMA, PMEA,[80] 4-ETA and 4-MTA. These are the N-methyl, N-ethyl, 4-ethoxy and 4-methylthio analogues of PMA, respectively. PMMA and PMEA are anecdotally weaker, more "ecstasy-like" and somewhat less dangerous than PMA itself, but can still produce nausea and hyperthermia similar to that produced by PMA, albeit at slightly higher doses. 4-EtOA was briefly sold in Canada in the 1970s, but little is known about it.[1] 4-MTA, however, is even more dangerous than PMA and produces strong serotonergic effects and intense hyperthermia, but with little to no euphoria, and was implicated in several deaths in the late 1990s.

Drug test false positives

PMA is formed as a metabolite by mebeverine and can result in false positives on drug tests for "ecstasy".[81]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 "#97 4-MA". Pihkal: A Chemical Love Story. Transform Press. 1991. ISBN 978-0-9630096-0-9. http://www.erowid.org/library/books_online/pihkal/pihkal097.shtml. Retrieved 2005-12-11. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. https://books.google.com/books?id=68-huAAACAAJ. Retrieved 2 November 2024. 
  3. ↑ Drug Enforcement Administration October 2000. The Hallucinogen PMA: Dancing With Death
  4. ↑ "Warning of possible shift to killer drug". Sydney Morning Herald (Fairfax). 7 April 2008. http://news.smh.com.au/national/warning-of-possible-shift-to-killer-drug-20080407-2482.html. 
  5. ↑ 5.0 5.1 "The reinforcing and discriminative stimulus properties of para-ethoxy- and para-methoxyamphetamine". Pharmacology, Biochemistry, and Behavior 41 (1): 165–169. January 1992. doi:10.1016/0091-3057(92)90077-S. PMID 1539067. 
  6. ↑ "Paramethoxymethamphetamine (Mitsubishi turbo) abuse: Case report and literature review". European Psychiatry 41 (S1): s875. April 2017. doi:10.1016/j.eurpsy.2017.01.1762. 
  7. ↑ "Comparative behavioural and neurochemical studies with a psychomotor stimulant, an hallucinogen and 3,4-methylenedioxy analogues of amphetamine". Psychopharmacology 118 (3): 295–304. April 1995. doi:10.1007/BF02245958. PMID 7617822. 
  8. ↑ "The stimulus properties of para-methoxyamphetamine: a nonessential serotonergic component". Pharmacology, Biochemistry, and Behavior 20 (2): 201–203. February 1984. doi:10.1016/0091-3057(84)90242-9. PMID 6546992. 
  9. ↑ "EcstasyData.org: Results : Lab Test Results for Recreational Drugs". https://www.ecstasydata.org/results.php?start=0&search_field=all&s=pma. 
  10. ↑ 10.0 10.1 "Warning over fake ecstasy tablets after seven people die in Scotland". The Guardian. 10 July 2013. https://www.theguardian.com/society/2013/jul/10/fake-ecstasy-warning-die-scotland. 
  11. ↑ 11.0 11.1 "Four Dead Amid Fears Of Dodgy Batch Of 'Superman' Ecstasy Hitting The UK". HuffPost UK. 2 January 2015. https://www.huffingtonpost.co.uk/2015/01/02/pmma-pma-bad-batch-mdma_n_6405956.html. 
  12. ↑ 12.0 12.1 "Amphetamine derivative fatalities in South Australia--is "Ecstasy" the culprit?". The American Journal of Forensic Medicine and Pathology 19 (3): 261–265. September 1998. doi:10.1097/00000433-199809000-00013. PMID 9760094. 
  13. ↑ "Anise oil as para-methoxyamphetamine (PMA) precursor". Forensic Science International 133 (1–2): 159–170. April 2003. doi:10.1016/S0379-0738(03)00063-X. PMID 12742705. 
  14. ↑ "Three cases of fatal paramethoxyamphetamine overdose". Journal of Analytical Toxicology 25 (7): 649–651. October 2001. doi:10.1093/jat/25.7.649. PMID 11599618. 
  15. ↑ "A fatal paramethoxymethamphetamine intoxication". Legal Medicine 5 (Suppl 1): S138–S141. March 2003. doi:10.1016/s1344-6223(02)00096-2. PMID 12935573. 
  16. ↑ "Amphetamine toxicity in the emergency department". European Journal of Emergency Medicine 12 (4): 193–197. August 2005. doi:10.1097/00063110-200508000-00010. PMID 16034267. 
  17. ↑ "The designer drug situation in Ibiza". Forensic Science International 140 (2–3): 195–206. March 2004. doi:10.1016/j.forsciint.2003.11.021. PMID 15036441. 
  18. ↑ "Fatality due to combined use of the designer drugs MDMA and PMA: a distribution study". Journal of Analytical Toxicology 27 (5): 318–322. 1 July 2003. doi:10.1093/jat/27.5.318. PMID 12908947. 
  19. ↑ "Dancing with "death": p-methoxyamphetamine overdose and its acute management". Journal of Toxicology. Clinical Toxicology 41 (2): 143–154. 2003. doi:10.1081/CLT-120019130. PMID 12733852. 
  20. ↑ 20.0 20.1 "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse 39 (1): 32–41. January 2001. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707. 
  21. ↑ 21.0 21.1 "Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products". Neuropsychopharmacology 38 (4): 552–562. 2013. doi:10.1038/npp.2012.204. PMID 23072836. 
  22. ↑ 22.0 22.1 "The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue". Neuropsychopharmacology 37 (5): 1192–1203. 2012. doi:10.1038/npp.2011.304. PMID 22169943. 
  23. ↑ 23.0 23.1 23.2 23.3 23.4 23.5 "Dopamine-releasing agents". Dopamine Transporters: Chemistry, Biology and Pharmacology. Hoboken [NJ]: Wiley. July 2008. pp. 305–320. ISBN 978-0-470-11790-3. OCLC 181862653. https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf. 
  24. ↑ 24.0 24.1 24.2 24.3 Vekariya R (2012). Towards Understanding the Mechanism of Action of Abused Cathinones (Master of Science thesis). Virginia Commonwealth University. doi:10.25772/AR93-7024 – via VCU Theses and Dissertations.
  25. ↑ 25.0 25.1 25.2 25.3 "The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse". J Med Chem 60 (7): 2605–2628. April 2017. doi:10.1021/acs.jmedchem.7b00085. PMID 28244748. "Table 5. Action of MDMA, MDA, and PMMA as Releasing Agents at the Serotonin (SERT), Dopamine (DAT), and Norepinephrine (NET) Transporters18,59,60 [...] a Data, although from different publications, were obtained from the same laboratory.". 
  26. ↑ 26.0 26.1 "Drug Discrimination and Mechanisms of Drug Action". Drug Discrimination. Wiley. 5 August 2011. pp. 183–216. doi:10.1002/9781118023150.ch6. ISBN 978-0-470-43352-2. "PMMA is a 5-HT releasing agent. S(+)PMMA is a potent releaser of 5-HT (EC50 = 41 nM) and NE (EC50 = 147 nM) with reduced activity as a releaser of DA (EC50 = 1,000 nM); the R(−)isomer of PMMA is a releaser of 5-HT (EC50 = 134 nM) with reduced potency for release of NE (EC50 = 1,600 nM) and DA (EC50 > 14,000 nM) (R.B. Rothman, unpublished data)." 
  27. ↑ "Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs". The Journal of Pharmacology and Experimental Therapeutics 313 (2): 848–854. May 2005. doi:10.1124/jpet.104.080101. PMID 15677348. 
  28. ↑ 28.0 28.1 Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines. 22 May 2012. https://scholarworks.uno.edu/td/1436/. Retrieved 4 November 2024. 
  29. ↑ "N-Alkylated Analogs of 4-Methylamphetamine (4-MA) Differentially Affect Monoamine Transporters and Abuse Liability". Neuropsychopharmacology 42 (10): 1950–1961. September 2017. doi:10.1038/npp.2017.98. PMID 28530234. 
  30. ↑ Sakloth F (11 December 2015). Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action. Theses and Dissertations (Ph.D. thesis). Virginia Commonwealth University. doi:10.25772/AY8R-PW77. Retrieved 24 November 2024 – via VCU Scholars Compass.
  31. ↑ 31.0 31.1 "Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones". Neuropharmacology 245. March 2024. doi:10.1016/j.neuropharm.2023.109827. PMID 38154512. 
  32. ↑ 32.0 32.1 Nicole L (2022). In vivo Structure-Activity Relationships of Substituted Amphetamines and Substituted Cathinones (Ph.D. thesis). The University of Arkansas for Medical Sciences. ProQuest 2711781450. Retrieved 5 December 2024. FIGURE 2-6: Release: Effects of the specified test drug on monoamine release by DAT (red circles), NET (blue squares), and SERT (black traingles) in rat brain tissue. [...] EC50 values determined for the drug indicated within the panel. [...]
  33. ↑ "Neuropharmacology of Synthetic Cathinones". Handb Exp Pharmacol. Handbook of Experimental Pharmacology 252: 113–142. 2018. doi:10.1007/164_2018_178. ISBN 978-3-030-10560-0. PMID 30406443. 
  34. ↑ 34.0 34.1 "The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes". Psychopharmacology 236 (3): 915–924. March 2019. doi:10.1007/s00213-018-5063-9. PMID 30341459. 
  35. ↑ Shalabi AR (14 December 2017). Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters. Theses and Dissertations (Ph.D. thesis). Virginia Commonwealth University. doi:10.25772/M4E1-3549. Retrieved 24 November 2024 – via VCU Scholars Compass.
  36. ↑ 36.0 36.1 "Systematic Structure-Activity Studies on Selected 2-, 3-, and 4-Monosubstituted Synthetic Methcathinone Analogs as Monoamine Transporter Releasing Agents". ACS Chem Neurosci 10 (1): 740–745. January 2019. doi:10.1021/acschemneuro.8b00524. PMID 30354055. 
  37. ↑ 37.0 37.1 "Quantitative structure-activity relationship analysis of the pharmacology of para-substituted methcathinone analogues". Br J Pharmacol 172 (10): 2433–2444. May 2015. doi:10.1111/bph.13030. PMID 25438806. 
  38. ↑ "Monoamine transporters and psychostimulant drugs". Eur J Pharmacol 479 (1–3): 23–40. October 2003. doi:10.1016/j.ejphar.2003.08.054. PMID 14612135. 
  39. ↑ "Therapeutic potential of monoamine transporter substrates". Current Topics in Medicinal Chemistry 6 (17): 1845–1859. 2006. doi:10.2174/156802606778249766. PMID 17017961. https://zenodo.org/record/1235860. 
  40. ↑ "Pharmacological evidence for the central serotonergic effects of monomethoxyamphetamines". The Journal of Pharmacology and Experimental Therapeutics 197 (2): 272–279. May 1976. doi:10.1016/S0022-3565(25)30506-9. PMID 946817. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=946817. 
  41. ↑ 41.0 41.1 "Effect of para-methoxyamphetamine on catecholamine metabolism in the mouse brain". Life Sciences 10 (19 Pt. 1): 1087–1095. October 1971. doi:10.1016/0024-3205(71)90227-x. PMID 5132700. 
  42. ↑ 42.0 42.1 "Comparative actions of monomethoxyamphetamines on the release and uptake of biogenic amines in brain tissue". The Journal of Pharmacology and Experimental Therapeutics 197 (2): 263–271. May 1976. doi:10.1016/S0022-3565(25)30505-7. PMID 1271280. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=1271280. 
  43. ↑ 43.0 43.1 43.2 43.3 "Monoamine transporter and receptor interaction profiles of a new series of designer cathinones". Neuropharmacology 79: 152–160. April 2014. doi:10.1016/j.neuropharm.2013.11.008. PMID 24275046. 
  44. ↑ "5-hydroxytryptamine- and dopamine-releasing effects of ring-substituted amphetamines on rat brain: a comparative study using in vivo microdialysis". Eur Neuropsychopharmacol 24 (8): 1362–1370. August 2014. doi:10.1016/j.euroneuro.2014.04.009. PMID 24862256. 
  45. ↑ 45.0 45.1 45.2 "Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat". Progress in Neuro-Psychopharmacology & Biological Psychiatry 24 (6): 955–977. August 2000. doi:10.1016/S0278-5846(00)00113-5. PMID 11041537. 
  46. ↑ "p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo". The Journal of Pharmacy and Pharmacology 32 (4): 262–266. April 1980. doi:10.1111/j.2042-7158.1980.tb12909.x. PMID 6103055. 
  47. ↑ 47.0 47.1 "Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain". Naunyn-Schmiedeberg's Archives of Pharmacology 324 (2): 79–87. September 1983. doi:10.1007/BF00497011. PMID 6646243. 
  48. ↑ "Amphetamine Derivatives as Monoamine Oxidase Inhibitors". Front Pharmacol 10. 2019. doi:10.3389/fphar.2019.01590. PMID 32038257. 
  49. ↑ "Central serotonin receptors as targets for drug research". J Med Chem 30 (1): 1–12. January 1987. doi:10.1021/jm00384a001. PMID 3543362. "Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites". 
  50. ↑ "5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA)". Eur J Pharmacol 102 (1): 23–29. June 1984. doi:10.1016/0014-2999(84)90333-9. PMID 6479216. 
  51. ↑ "Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane". J Med Chem 25 (10): 1163–1168. October 1982. doi:10.1021/jm00352a013. PMID 7143352. 
  52. ↑ "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav 22 (5): 723–729. May 1985. doi:10.1016/0091-3057(85)90520-9. PMID 3839309. 
  53. ↑ "Effects of 3,4-methylenedioxymethamphetamine and related amphetamines on autonomic and behavioral thermoregulation". Pharmacology, Biochemistry, and Behavior 81 (3): 485–496. July 2005. doi:10.1016/j.pbb.2005.04.005. PMID 15904952. 
  54. ↑ "Differences in the in vivo dynamics of neurotransmitter release and serotonin uptake after acute para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine revealed by chronoamperometry". Neurochemistry International 47 (5): 350–361. October 2005. doi:10.1016/j.neuint.2005.04.026. PMID 15979209. 
  55. ↑ "Pharmacological and behavioral determinants of cocaine, methamphetamine, 3,4-methylenedioxymethamphetamine, and para-methoxyamphetamine-induced hyperthermia". Psychopharmacology 194 (1): 41–52. September 2007. doi:10.1007/s00213-007-0825-9. PMID 17530474. 
  56. ↑ "Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects". Acta Anaesthesiologica Scandinavica 47 (10): 1298–1299. November 2003. doi:10.1046/j.1399-6576.2003.00245.x. PMID 14616331. 
  57. ↑ "Synthesis of arylpropylamines; from allyl chloride". J Am Chem Soc 68: 1009–1011. June 1946. doi:10.1021/ja01210a032. PMID 20985610. 
  58. ↑ DEA. "The Hallucinogen PMA: Dancing With Death". http://www.erowid.org/chemicals/pma/pma_dea_intellbrief.pdf. 
  59. ↑ "Recent paramethoxyamphetamine deaths". Journal of Analytical Toxicology 22 (2): 169–172. 1 March 1998. doi:10.1093/jat/22.2.169. PMID 9547415. 
  60. ↑ "Caveat Emptor: Death involving the use of 4-methoxyamphetamine". Journal of Clinical Forensic Medicine 9 (3): 160. September 2002. doi:10.1016/S1353-1131(02)00043-3. PMID 15274949. 
  61. ↑ "Fatal paramethoxy-amphetamine (PMA) poisoning in the Australian Capital Territory". The Medical Journal of Australia 188 (7): 426. April 2008. doi:10.5694/j.1326-5377.2008.tb01695.x. PMID 18393753. 
  62. ↑ "Renewed warning over 'Rolex' pills". BBC News. 24 July 2013. https://www.bbc.com/news/uk-northern-ireland-23440537. 
  63. ↑ "WATCH OUT FOR DANGEROUS SUPERMAN PILL - News - Deep House Amsterdam". 30 January 2014. http://www.deephouseamsterdam.com/watch-out-for-dangerous-superman-pill/. 
  64. ↑ "¿Qué es Superman, la droga que ya ha cobrado varias vidas en el mundo?" (in Spanish). ElPais. 18 April 2016. http://www.elpais.com.uy/mundo/superman-droga-que-mezcla-metanfetamina-extasis.html. 
  65. ↑ "Las claves para entender qué pasó". La Nación. 2016-04-17. http://www.lanacion.com.ar/1890180-las-claves-para-entender-que-paso. 
  66. ↑ "Drug Warning – Reagent Tests UK". https://www.reagent-tests.uk/blog/category/drug-warning/. 
  67. ↑ "Annual Estimates Of Requirements Of Narcotic Drugs, Manufacture Of Synthetic Drugs, Opium Production And Cultivation Of The…". http://www.incb.org/pdf/e/list/green.pdf. 
  68. ↑ 68.0 68.1 Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
  69. ↑ "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  70. ↑ "Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista annetun valtioneuvoston asetuksen muuttamisesta" (in Finnish). Finlex. Helsinki: Finland's Ministry of Justice. 25 October 2018. https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2018/839. 
  71. ↑ "Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista annetun valtioneuvoston asetuksen muuttamisesta" (in Finnish). Finlex. Helsinki: Finland's Ministry of Justice. 13 January 2022. https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2022/13. 
  72. ↑ "Doden na gebruik speed met 4-MA" (in nl). 13 June 2012. http://nos.nl/artikel/383346-schippers-verbiedt-dodelijk-4ma.html. 
  73. ↑ "List of Controlled Drugs" (in en). 2013-08-13. https://www.release.org.uk/law/list-controlled-drugs. 
  74. ↑ 21 CFR 1308.11
  75. ↑ "Caveat Emptor: Death involving the use of 4-methoxyamphetamine". Journal of Clinical Forensic Medicine 9 (3): 160. September 2002. doi:10.1016/s1353-1131(02)00043-3. PMID 15274949. 
  76. ↑ "Drug Info". http://dancesafe.org/documents/druginfo/pma_faq.php. 
  77. ↑ "Warning: pills sold as ecstasy found to contain PMA". http://ecstasy.org/testing/pma.html. 
  78. ↑ Chamberlin T, Murray D. NET Syndicated QLD News 'Louis Vuitton' designer death drug hits the streets
  79. ↑ "Fatalities caused by the MDMA-related drug paramethoxyamphetamine (PMA)". Journal of Analytical Toxicology 25 (7): 645–648. October 2001. doi:10.1093/jat/25.7.645. PMID 11599617. 
  80. ↑ "The Characterization of 4-Methoxy-N-ethylamphetamine Hydrochloride". Microgram Journal 4 (1–4): 42–46. 2006. 
  81. ↑ "Мебеверин (Mebeverine)" (in ru). https://aipsin.com/newsubstance/333/. 



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