Para-Methoxyamphetamine

{{Short description|Chemical compound}} {{DISPLAYTITLE:''para''-Methoxyamphetamine}} {{Distinguish|4-methylamphetamine|4-MA steroid}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | Verifiedfields = changed | verifiedrevid = 461747299 | drug_name = PMA | image = PMA structure.svg | image_class = skin-invert-image | width = 250px | image2 = 4-Methoxyamphetamine_molecule_ball.png | image_class2 = bg-transparent | width2 = 250px

| tradename = | pregnancy_category = | routes_of_administration = Oral<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /> | class = Serotonin releasing agent; Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen; Monoamine oxidase inhibitor | ATC_prefix = None | ATC_suffix =

| legal_AU = S9 | legal_BR = F2 | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}</ref> | legal_CA = Schedule I | legal_DE = Anlage I | legal_UK = Class A | legal_US = Schedule I | legal_UN = P I | legal_status = In general illegal unless for medical, therapeutic or scientific use.

| CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 64-13-1 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = OVB8F8P39Q | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01472 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 278663 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C22811 | PubChem = 31721 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 29417 | synonyms = ''para''-Methoxyamphetamine; ''p''-Methoxyamphetamine; PMA; 4-Methoxyamphetamine; 4-MA; 4-MeO-A; 4-OMe-PIA

| IUPAC_name = 1-(4-methoxyphenyl)propan-2-amine | C = 10 | H = 15 | N = 1 | O = 1 | SMILES = C1=CC(=CC=C1CC(C)N)OC | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C10H15NO/c1-8(11)7-9-3-5-10(12-2)6-4-9/h3-6,8H,7,11H2,1-2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = NEGYEDYHPHMHGK-UHFFFAOYSA-N }}

'''''para''-Methoxyamphetamine''' ('''PMA'''), also known as '''4-methoxyamphetamine''' ('''4-MA'''), is a designer drug of the amphetamine class with serotonergic effects.<ref>Drug Enforcement Administration October 2000. [http://www.erowid.org/chemicals/pma/pma_dea_intellbrief.pdf The Hallucinogen PMA: Dancing With Death] {{Webarchive|url=https://web.archive.org/web/20071204021053/http://erowid.org/chemicals/pma/pma_dea_intellbrief.pdf |date=2007-12-04 }}</ref><ref name="PiHKAL">{{cite book |vauthors=Shulgin AT, Shulgin A |title=Pihkal: A Chemical Love Story |date=1991 |publisher=Transform Press |isbn=978-0-9630096-0-9 |chapter-url=http://www.erowid.org/library/books_online/pihkal/pihkal097.shtml |chapter=#97 4-MA |access-date=2005-12-11 |archive-date=2007-04-08 |archive-url=https://web.archive.org/web/20070408002536/http://www.erowid.org/library/books_online/pihkal/pihkal097.shtml |url-status=live }}</ref><ref name="salna">{{cite news|vauthors= Karlis S|title= Warning of possible shift to killer drug|url= http://news.smh.com.au/national/warning-of-possible-shift-to-killer-drug-20080407-2482.html|work= Sydney Morning Herald|publisher= Fairfax|date= 7 April 2008|access-date= 2008-06-29|archive-date= 2008-07-02|archive-url= https://web.archive.org/web/20080702035335/http://news.smh.com.au/national/warning-of-possible-shift-to-killer-drug-20080407-2482.html|url-status= live}}</ref> Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or entactogenic effects,<ref name="pmid1539067">{{cite journal | vauthors = Corrigall WA, Robertson JM, Coen KM, Lodge BA | title = The reinforcing and discriminative stimulus properties of para-ethoxy- and para-methoxyamphetamine | journal = Pharmacology, Biochemistry, and Behavior | volume = 41 | issue = 1 | pages = 165–169 | date = January 1992 | pmid = 1539067 | doi = 10.1016/0091-3057(92)90077-S | s2cid = 30080516 | citeseerx = 10.1.1.670.6929 }}</ref> and behaves more like an antidepressant in comparison,<ref>{{cite journal | vauthors = Preve M, Suardi NE, Godio M, Traber R, Colombo RA |title=Paramethoxymethamphetamine (Mitsubishi turbo) abuse: Case report and literature review |journal=European Psychiatry |date=April 2017 |volume=41 |issue=S1 |pages=s875 |doi=10.1016/j.eurpsy.2017.01.1762 |s2cid=148876431 }}</ref> though it does have some psychedelic properties.<ref name="pmid7617822">{{cite journal | vauthors = Hegadoren KM, Martin-Iverson MT, Baker GB | title = Comparative behavioural and neurochemical studies with a psychomotor stimulant, an hallucinogen and 3,4-methylenedioxy analogues of amphetamine | journal = Psychopharmacology | volume = 118 | issue = 3 | pages = 295–304 | date = April 1995 | pmid = 7617822 | doi = 10.1007/BF02245958 | s2cid = 30756295 }}</ref><ref name="pmid6546992">{{cite journal | vauthors = Winter JC | title = The stimulus properties of para-methoxyamphetamine: a nonessential serotonergic component | journal = Pharmacology, Biochemistry, and Behavior | volume = 20 | issue = 2 | pages = 201–203 | date = February 1984 | pmid = 6546992 | doi = 10.1016/0091-3057(84)90242-9 | s2cid = 9673028 }}</ref>

PMA has been found in black market tablets sold as MDMA (ecstasy)<ref name="ecstasydata">{{cite web|url=https://www.ecstasydata.org/results.php?start=0&search_field=all&s=pma|title=EcstasyData.org: Results : Lab Test Results for Recreational Drugs|website=www.ecstasydata.org|access-date=2015-02-15|archive-date=2015-02-15|archive-url=https://web.archive.org/web/20150215150551/https://www.ecstasydata.org/results.php?start=0&search_field=all&s=pma|url-status=live}}</ref><ref name="fake-ecstasy-warning-die-scotland">{{cite news|vauthors=Davies C|title=Warning over fake ecstasy tablets after seven people die in Scotland|url=https://www.theguardian.com/society/2013/jul/10/fake-ecstasy-warning-die-scotland|access-date=10 July 2013|newspaper=The Guardian|date=10 July 2013|archive-date=2 February 2020|archive-url=https://web.archive.org/web/20200202193438/https://www.theguardian.com/society/2013/jul/10/fake-ecstasy-warning-die-scotland|url-status=live}}</ref><ref name=Barrell2015>{{cite news |vauthors=Barrell R |title=Four Dead Amid Fears Of Dodgy Batch Of 'Superman' Ecstasy Hitting The UK |url=https://www.huffingtonpost.co.uk/2015/01/02/pmma-pma-bad-batch-mdma_n_6405956.html |work=HuffPost UK |date=2 January 2015 |access-date=12 June 2022 |archive-date=21 April 2022 |archive-url=https://web.archive.org/web/20220421194300/https://www.huffingtonpost.co.uk/2015/01/02/pmma-pma-bad-batch-mdma_n_6405956.html |url-status=live }}</ref><ref name="pmid9760094">{{cite journal | vauthors = Byard RW, Gilbert J, James R, Lokan RJ | title = Amphetamine derivative fatalities in South Australia--is "Ecstasy" the culprit? | journal = The American Journal of Forensic Medicine and Pathology | volume = 19 | issue = 3 | pages = 261–265 | date = September 1998 | pmid = 9760094 | doi = 10.1097/00000433-199809000-00013 }}</ref> 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.<ref>{{cite journal | vauthors = Waumans D, Bruneel N, Tytgat J | title = Anise oil as para-methoxyamphetamine (PMA) precursor | journal = Forensic Science International | volume = 133 | issue = 1–2 | pages = 159–170 | date = April 2003 | pmid = 12742705 | doi = 10.1016/S0379-0738(03)00063-X }}</ref>

==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{{nbsp}}mg orally included hypertension, diethyltryptamine (DET)-reminiscent effects, distinct after-images, and some paresthesia, "intoxication" or alcohol-like intoxication, and no psychedelic effects.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011">{{cite book | vauthors = Shulgin A, Manning T, Daley P | title=The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | publisher=Transform Press | location=Berkeley | volume=1 | year=2011 | isbn=978-0-9630096-3-0 | url=https://books.google.com/books?id=68-huAAACAAJ | access-date=2 November 2024}}</ref> In clinical studies, PMA produced excitation, other central effects, and sympathomimetic effects, but similarly no psychotomimetic effects.<ref name="ShulginManningDaley2011" />

==Adverse effects== PMA has been associated with numerous adverse reactions including death.<ref>{{cite journal | vauthors = Martin TL | title = Three cases of fatal paramethoxyamphetamine overdose | journal = Journal of Analytical Toxicology | volume = 25 | issue = 7 | pages = 649–651 | date = October 2001 | pmid = 11599618 | doi = 10.1093/jat/25.7.649 | doi-access = free }}</ref><ref>{{cite journal | vauthors = Becker J, Neis P, Röhrich J, Zörntlein S | title = A fatal paramethoxymethamphetamine intoxication | journal = Legal Medicine | volume = 5 | issue = Suppl 1 | pages = S138–S141 | date = March 2003 | pmid = 12935573 | doi = 10.1016/s1344-6223(02)00096-2 }}</ref> 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.<ref>{{cite journal | vauthors = Smets G, Bronselaer K, De Munnynck K, De Feyter K, Van de Voorde W, Sabbe M | title = Amphetamine toxicity in the emergency department | journal = European Journal of Emergency Medicine | volume = 12 | issue = 4 | pages = 193–197 | date = August 2005 | pmid = 16034267 | doi = 10.1097/00063110-200508000-00010 | s2cid = 40206693 }}</ref> While PMA alone may cause significant toxicity, the combination of PMA with MDMA has a synergistic effect that seems to be particularly hazardous.<ref>{{cite journal | vauthors = Lora-Tamayo C, Tena T, Rodríguez A, Moreno D, Sancho JR, Enseñat P, Muela F | title = The designer drug situation in Ibiza | journal = Forensic Science International | volume = 140 | issue = 2–3 | pages = 195–206 | date = March 2004 | pmid = 15036441 | doi = 10.1016/j.forsciint.2003.11.021 }}</ref> 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.<ref>{{cite journal | vauthors = Dams R, De Letter EA, Mortier KA, Cordonnier JA, Lambert WE, Piette MH, Van Calenbergh S, De Leenheer AP | title = Fatality due to combined use of the designer drugs MDMA and PMA: a distribution study | journal = Journal of Analytical Toxicology | volume = 27 | issue = 5 | pages = 318–322 | date = 1 July 2003 | pmid = 12908947 | doi = 10.1093/jat/27.5.318 | doi-access = free }}</ref>

==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.<ref name="pmid12733852">{{cite journal | vauthors = Caldicott DG, Edwards NA, Kruys A, Kirkbride KP, Sims DN, Byard RW, Prior M, Irvine RJ | title = Dancing with "death": p-methoxyamphetamine overdose and its acute management | journal = Journal of Toxicology. Clinical Toxicology | volume = 41 | issue = 2 | pages = 143–154 | year = 2003 | pmid = 12733852 | doi = 10.1081/CLT-120019130 | s2cid = 39578828 }}</ref>

==Pharmacology== ===Pharmacodynamics=== ====Actions==== {| class="wikitable floatright" style="font-size:small;" |+ {{Nowrap|Monoamine release of {{Abbrlink|PMA|para-methoxyamphetamine}} and related agents ({{Abbrlink|EC50|Half maximal effective concentration}}, nM)}} |- ! Compound !! {{abbrlink|5-HT|Serotonin}} !! {{abbrlink|NE|Norepinephrine}} !! {{abbrlink|DA|Dopamine}} !! Ref |- | ''d''-Amphetamine || 698–1,765 || 6.6–7.2 || 5.8–24.8 || <ref name="RothmanBaumannDersch2001">{{cite journal | vauthors = Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS | title = Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin | journal = Synapse | volume = 39 | issue = 1 | pages = 32–41 | date = January 2001 | pmid = 11071707 | doi = 10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3 | url = }}</ref><ref name="BaumannPartillaLehner2013">{{cite journal | vauthors = Baumann MH, Partilla JS, Lehner KR, Thorndike EB, Hoffman AF, Holy M, Rothman RB, Goldberg SR, Lupica CR, Sitte HH, Brandt SD, Tella SR, Cozzi NV, Schindler CW | title = Powerful cocaine-like actions of 3,4-methylenedioxypyrovalerone (MDPV), a principal constituent of psychoactive 'bath salts' products | journal = Neuropsychopharmacology | volume = 38 | issue = 4 | pages = 552–562 | year = 2013 | pmid = 23072836 | pmc = 3572453 | doi = 10.1038/npp.2012.204 }}</ref> |- | ''d''-Methamphetamine || 736–1,292 || 12.3–13.8 || 8.5–24.5 || <ref name="RothmanBaumannDersch2001" /><ref name="BaumannAyestasPartilla2012">{{cite journal | vauthors = Baumann MH, Ayestas MA, Partilla JS, Sink JR, Shulgin AT, Daley PF, Brandt SD, Rothman RB, Ruoho AE, Cozzi NV | title = The designer methcathinone analogs, mephedrone and methylone, are substrates for monoamine transporters in brain tissue | journal = Neuropsychopharmacology | volume = 37 | issue = 5 | pages = 1192–1203 | year = 2012 | pmid = 22169943 | pmc = 3306880 | doi = 10.1038/npp.2011.304 }}</ref> |- | 2-Methoxyamphetamine || {{Abbr|ND|No data}} || 473 || 1,478 || <ref name="Blough2008">{{cite book | vauthors = Blough B | chapter = Dopamine-releasing agents | veditors = Trudell ML, Izenwasser S | title = Dopamine Transporters: Chemistry, Biology and Pharmacology | pages = 305–320 | date = July 2008 | isbn = 978-0-470-11790-3 | oclc = 181862653 | ol = OL18589888W | publisher = Wiley | location = Hoboken [NJ] | doi = | url = https://books.google.com/books?id=QCagLAAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/Dopamine-releasing-agents_c11.pdf }}</ref> |- | 3-Methoxyamphetamine || {{Abbr|ND|No data}} || 58.0 || 103 || <ref name="Blough2008" /> |- | ''para''-Methoxyamphetamine (PMA) || {{Abbr|ND|No data}} || 166 || 867 || <ref name="Blough2008" /><ref name="Vekariya2012">{{cite thesis | vauthors = Vekariya R | degree = Master of Science | title=Towards Understanding the Mechanism of Action of Abused Cathinones | publisher = Virginia Commonwealth University | via =VCU Theses and Dissertations | date=2012 | doi=10.25772/AR93-7024 | page=}}</ref> |- | {{Abbrlink|PMMA|para-Methoxymethamphetamine}} || {{Abbr|ND|No data}} || {{Abbr|ND|No data}} || {{Abbr|ND|No data}} || {{Abbr|ND|No data}} |- | {{nbsp}}{{nbsp}}(''S'')-PMMA || 41 || 147 || 1,000 || <ref name="Glennon2017">{{cite journal | vauthors = Glennon RA | title = The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse | journal = J Med Chem | volume = 60 | issue = 7 | pages = 2605–2628 | date = April 2017 | pmid = 28244748 | pmc = 5824997 | doi = 10.1021/acs.jmedchem.7b00085 | url = | quote = 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.}}</ref><ref name="GlennonYoung2011">{{cite book | vauthors=Glennon RA, Young R | title=Drug Discrimination | chapter=Drug Discrimination and Mechanisms of Drug Action | publisher=Wiley | date=5 August 2011 | isbn=978-0-470-43352-2 | doi=10.1002/9781118023150.ch6 | pages=183–216 | quote=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).}}</ref><ref name="Vekariya2012" /> |- | {{nbsp}}{{nbsp}}(''R'')-PMMA || 134 || >14,000 || 1,600 || <ref name="Glennon2017" /><ref name="GlennonYoung2011" /><ref name="Vekariya2012" /> |- | 4-Methylamphetamine (4-MA) || 53.4 || 22.2 || 44.1 || <ref name="WeeAndersonBaumann2005">{{cite journal | vauthors = Wee S, Anderson KG, Baumann MH, Rothman RB, Blough BE, Woolverton WL | title = Relationship between the serotonergic activity and reinforcing effects of a series of amphetamine analogs | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 313 | issue = 2 | pages = 848–854 | date = May 2005 | pmid = 15677348 | doi = 10.1124/jpet.104.080101 | s2cid = 12135483 }}</ref><ref name="Forsyth2012">{{cite journal | vauthors = Forsyth AN | title=Synthesis and Biological Evaluation of Rigid Analogues of Methamphetamines | website=ScholarWorks@UNO | date=22 May 2012 | url=https://scholarworks.uno.edu/td/1436/ | access-date=4 November 2024}}</ref><ref name="Blough2008" /> |- | 4-Methylmethamphetamine (4-MMA) || 67.4 || 66.9 || 41.3 || <ref name="SolisPartillaSakloth2017">{{cite journal | vauthors = Solis E, Partilla JS, Sakloth F, Ruchala I, Schwienteck KL, De Felice LJ, Eltit JM, Glennon RA, Negus SS, Baumann MH | title = N-Alkylated Analogs of 4-Methylamphetamine (4-MA) Differentially Affect Monoamine Transporters and Abuse Liability | journal = Neuropsychopharmacology | volume = 42 | issue = 10 | pages = 1950–1961 | date = September 2017 | pmid = 28530234 | pmc = 5561352 | doi = 10.1038/npp.2017.98 | url = }}</ref><ref name="Sakloth2015">{{cite thesis | vauthors = Sakloth F | degree = Ph.D. | title=Psychoactive synthetic cathinones (or 'bath salts'): Investigation of mechanisms of action | work = Theses and Dissertations | publisher = Virginia Commonwealth University | via = VCU Scholars Compass | date=11 December 2015 | doi=10.25772/AY8R-PW77 | url=https://scholarscompass.vcu.edu/etd/4041/ | access-date=24 November 2024}}</ref> |- | ''para''-Chloroamphetamine (PCA) || 28.3 || 23.5–26.2 || 42.2–68.5 || <ref name="Forsyth2012" /><ref name="Blough2008" /><ref name="FitzgeraldGannonWalther2024">{{cite journal | vauthors = Fitzgerald LR, Gannon BM, Walther D, Landavazo A, Hiranita T, Blough BE, Baumann MH, Fantegrossi WE | title = Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones | journal = Neuropharmacology | volume = 245 | issue = | article-number = 109827 | date = March 2024 | pmid = 38154512 | doi = 10.1016/j.neuropharm.2023.109827 | pmc = 10842458 | url = }}</ref><ref name="Nicole2022">{{cite thesis | vauthors = Nicole L | degree = Ph.D. | publisher = The University of Arkansas for Medical Sciences | title=In vivo Structure-Activity Relationships of Substituted Amphetamines and Substituted Cathinones | date=2022 | url=https://www.proquest.com/docview/2711781450 | access-date=5 December 2024 | id = {{ProQuest|2711781450}} | quote = 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. [...]}}</ref> |- | ''para''-Chloromethamphetamine (PCMA) || 29.9 || 36.5 || 54.7 || <ref name="FitzgeraldGannonWalther2024" /><ref name="Nicole2022" /> |- | Methedrone (4-MeO-MC) || 120–195 || 111 || 506–881 || <ref name="BaumannWaltersNiello2018">{{cite journal | vauthors = Baumann MH, Walters HM, Niello M, Sitte HH | title = Neuropharmacology of Synthetic Cathinones | journal = Handb Exp Pharmacol | series = Handbook of Experimental Pharmacology | volume = 252 | issue = | pages = 113–142 | date = 2018 | pmid = 30406443 | pmc = 7257813 | doi = 10.1007/164_2018_178 | isbn = 978-3-030-10560-0 | url = }}</ref><ref name="BloughDeckerLandavazo2019">{{cite journal | vauthors = Blough BE, Decker AM, Landavazo A, Namjoshi OA, Partilla JS, Baumann MH, Rothman RB | title = The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes | journal = Psychopharmacology | volume = 236 | issue = 3 | pages = 915–924 | date = March 2019 | pmid = 30341459 | pmc = 6475490 | doi = 10.1007/s00213-018-5063-9 }}</ref><ref name="Shalabi2017">{{cite thesis | vauthors = Shalabi AR | degree = Ph.D. | title=Structure-Activity Relationship Studies of Bupropion and Related 3-Substituted Methcathinone Analogues at Monoamine Transporters | work = Theses and Dissertations | publisher = Virginia Commonwealth University | via = VCU Scholars Compass | date=14 December 2017 | doi=10.25772/M4E1-3549 | url=https://scholarscompass.vcu.edu/etd/5176/ | access-date=24 November 2024}}</ref><ref name="WaltherShalabiBaumann2019">{{cite journal | vauthors = Walther D, Shalabi AR, Baumann MH, Glennon RA | title = Systematic Structure-Activity Studies on Selected 2-, 3-, and 4-Monosubstituted Synthetic Methcathinone Analogs as Monoamine Transporter Releasing Agents | journal = ACS Chem Neurosci | volume = 10 | issue = 1 | pages = 740–745 | date = January 2019 | pmid = 30354055 | pmc = 8269283 | doi = 10.1021/acschemneuro.8b00524 | url = }}</ref><ref name="BonanoBanksKolanos2015">{{cite journal | vauthors = Bonano JS, Banks ML, Kolanos R, Sakloth F, Barnier ML, Glennon RA, Cozzi NV, Partilla JS, Baumann MH, Negus SS | title = Quantitative structure-activity relationship analysis of the pharmacology of para-substituted methcathinone analogues | journal = Br J Pharmacol | volume = 172 | issue = 10 | pages = 2433–2444 | date = May 2015 | pmid = 25438806 | pmc = 4409897 | doi = 10.1111/bph.13030 | url = }}</ref> |- | Mephedrone (4-MMC) || 118.3–122 || 58–62.7 || 49.1–51 || <ref name="BaumannAyestasPartilla2012" /><ref name="BaumannPartillaLehner2013" /><ref name="BloughDeckerLandavazo2019" /><ref name="WaltherShalabiBaumann2019" /><ref name="BonanoBanksKolanos2015" /> |- | colspan="5" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''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:''' <ref name="RothmanBaumann2003">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Monoamine transporters and psychostimulant drugs | journal = Eur J Pharmacol | volume = 479 | issue = 1–3 | pages = 23–40 | date = October 2003 | pmid = 14612135 | doi = 10.1016/j.ejphar.2003.08.054 | url = }}</ref><ref name="RothmanBaumann2006">{{cite journal | vauthors = Rothman RB, Baumann MH | title = Therapeutic potential of monoamine transporter substrates | journal = Current Topics in Medicinal Chemistry | volume = 6 | issue = 17 | pages = 1845–1859 | year = 2006 | pmid = 17017961 | doi = 10.2174/156802606778249766 | url = https://zenodo.org/record/1235860 }}</ref> |}

PMA acts as a selective serotonin releasing agent (SSRA) with weak effects on dopamine and norepinephrine transporters.<ref name="pmid946817">{{cite journal | vauthors = Menon MK, Tseng LF, Loh HH | title = Pharmacological evidence for the central serotonergic effects of monomethoxyamphetamines | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 197 | issue = 2 | pages = 272–279 | date = May 1976 | doi = 10.1016/S0022-3565(25)30506-9 | pmid = 946817 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=946817 | author-link3 = Horace Loh | url-access = subscription }}</ref><ref name="pmid5132700">{{cite journal | vauthors = Hitzemann RJ, Loh HH, Domino EF | title = Effect of para-methoxyamphetamine on catecholamine metabolism in the mouse brain | journal = Life Sciences | volume = 10 | issue = 19 Pt. 1| pages = 1087–1095 | date = October 1971 | pmid = 5132700 | doi = 10.1016/0024-3205(71)90227-x }}</ref><ref name="pmid1271280">{{cite journal | vauthors = Tseng LF, Menon MK, Loh HH | title = Comparative actions of monomethoxyamphetamines on the release and uptake of biogenic amines in brain tissue | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 197 | issue = 2 | pages = 263–271 | date = May 1976 | doi = 10.1016/S0022-3565(25)30505-7 | pmid = 1271280 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=1271280 | url-access = subscription }}</ref><ref name="SimmlerRickliHoener2014">{{cite journal | vauthors = Simmler LD, Rickli A, Hoener MC, Liechti ME | title = Monoamine transporter and receptor interaction profiles of a new series of designer cathinones | journal = Neuropharmacology | volume = 79 | issue = | pages = 152–160 | date = April 2014 | pmid = 24275046 | doi = 10.1016/j.neuropharm.2013.11.008 | url = }}</ref> Its {{Abbrlink|EC50|half-maximal effective concentration}} values for induction of monoamine release are 166{{nbsp}}nM for dopamine and 867{{nbsp}}nM for norepinephrine in rat brain synaptosomes, whereas serotonin was not reported.<ref name="Blough2008"/><ref name="Vekariya2012" /> The drug has been found to robustly increase brain serotonin levels and to weakly increase brain dopamine levels in rodents ''in vivo''.<ref name="MatsumotoMaenoKato2014">{{cite journal | vauthors = Matsumoto T, Maeno Y, Kato H, Seko-Nakamura Y, Monma-Ohtaki J, Ishiba A, Nagao M, Aoki Y | title = 5-hydroxytryptamine- and dopamine-releasing effects of ring-substituted amphetamines on rat brain: a comparative study using in vivo microdialysis | journal = Eur Neuropsychopharmacol | volume = 24 | issue = 8 | pages = 1362–1370 | date = August 2014 | pmid = 24862256 | doi = 10.1016/j.euroneuro.2014.04.009 | url = }}</ref> 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.<ref name="pmid11041537">{{cite journal | vauthors = Daws LC, Irvine RJ, Callaghan PD, Toop NP, White JM, Bochner F | title = Differential behavioural and neurochemical effects of para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine in the rat | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 24 | issue = 6 | pages = 955–977 | date = August 2000 | pmid = 11041537 | doi = 10.1016/S0278-5846(00)00113-5 | s2cid = 24347904 }}</ref>

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).<ref name="pmid6103055">{{cite journal | vauthors = Green AL, El Hait MA | title = p-Methoxyamphetamine, a potent reversible inhibitor of type-A monoamine oxidase in vitro and in vivo | journal = The Journal of Pharmacy and Pharmacology | volume = 32 | issue = 4 | pages = 262–266 | date = April 1980 | pmid = 6103055 | doi = 10.1111/j.2042-7158.1980.tb12909.x | s2cid = 42213032 }}</ref><ref name="pmid6646243">{{cite journal | vauthors = Ask AL, Fagervall I, Ross SB | title = Selective inhibition of monoamine oxidase in monoaminergic neurons in the rat brain | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 324 | issue = 2 | pages = 79–87 | date = September 1983 | pmid = 6646243 | doi = 10.1007/BF00497011 | s2cid = 403633 }}</ref> The {{Abbrlink|IC50|half-maximal inhibitory concentration}} of PMA for MAO-A inhibition has been reported to be 300 to 600{{nbsp}}nM.<ref name="Reyes-ParadaIturriaga-VasquezCassels2019">{{cite journal | vauthors = Reyes-Parada M, Iturriaga-Vasquez P, Cassels BK | title = Amphetamine Derivatives as Monoamine Oxidase Inhibitors | journal = Front Pharmacol | volume = 10 | issue = | article-number = 1590 | date = 2019 | pmid = 32038257 | pmc = 6989591 | doi = 10.3389/fphar.2019.01590 | doi-access = free | url = }}</ref>

PMA shows very low affinities for the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors.<ref name="SimmlerRickliHoener2014"/> Its affinities (Ki) for these receptors have been reported to be >20,000{{nbsp}}nM, 11,200{{nbsp}}nM, and >13,000{{nbsp}}nM, respectively.<ref name="SimmlerRickliHoener2014" /> 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{{nbsp}}nM and 33,600{{nbsp}}nM, respectively).<ref name="Glennon1987">{{cite journal | vauthors = Glennon RA | title = Central serotonin receptors as targets for drug research | journal = J Med Chem | volume = 30 | issue = 1 | pages = 1–12 | date = January 1987 | pmid = 3543362 | doi = 10.1021/jm00384a001 | url = | quote = Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites}}</ref><ref name="ShannonBattagliaGlennon1984">{{cite journal | vauthors = Shannon M, Battaglia G, Glennon RA, Titeler M | title = 5-HT1 and 5-HT2 binding properties of derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane (2,5-DMA) | journal = Eur J Pharmacol | volume = 102 | issue = 1 | pages = 23–29 | date = June 1984 | pmid = 6479216 | doi = 10.1016/0014-2999(84)90333-9 | url = }}</ref> On the other hand, PMA shows much higher affinities for the mouse and rat trace amine-associated receptor 1 (TAAR1).<ref name="SimmlerRickliHoener2014" />

====Effects==== PMA fails to substitute for the psychedelic drug DOM in rodent drug discrimination tests.<ref name="GlennonYoungBenington1982">{{cite journal | vauthors = Glennon RA, Young R, Benington F, Morin RD | title = Behavioral and serotonin receptor properties of 4-substituted derivatives of the hallucinogen 1-(2,5-dimethoxyphenyl)-2-aminopropane | journal = J Med Chem | volume = 25 | issue = 10 | pages = 1163–1168 | date = October 1982 | pmid = 7143352 | doi = 10.1021/jm00352a013 | url = }}</ref> It only partially substituted for the psychostimulant amphetamine in such tests.<ref name="ShulginManningDaley2011" /><ref name="Glennon2017" /><ref name="GlennonYoungHauck1985">{{cite journal | vauthors = Glennon RA, Young R, Hauck AE | title = Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology | journal = Pharmacol Biochem Behav | volume = 22 | issue = 5 | pages = 723–729 | date = May 1985 | pmid = 3839309 | doi = 10.1016/0091-3057(85)90520-9 | url = }}</ref> The drug did not substitute for MDMA in rodents, suggesting lack of entactogenic effects.<ref name="Glennon2017" /> 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.<ref name="pmid5132700"/><ref name="pmid1271280"/><ref name="pmid11041537"/> Accordingly, it is not self-administered by rodents unlike amphetamine and MDMA.<ref name="pmid1539067"/>

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.<ref name="pmid11041537"/><ref name="pmid6646243"/> 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).<ref>{{cite journal | vauthors = Jaehne EJ, Salem A, Irvine RJ | title = Effects of 3,4-methylenedioxymethamphetamine and related amphetamines on autonomic and behavioral thermoregulation | journal = Pharmacology, Biochemistry, and Behavior | volume = 81 | issue = 3 | pages = 485–496 | date = July 2005 | pmid = 15904952 | doi = 10.1016/j.pbb.2005.04.005 | s2cid = 9680452 }}</ref><ref>{{cite journal | vauthors = Callaghan PD, Irvine RJ, Daws LC | title = Differences in the in vivo dynamics of neurotransmitter release and serotonin uptake after acute para-methoxyamphetamine and 3,4-methylenedioxymethamphetamine revealed by chronoamperometry | journal = Neurochemistry International | volume = 47 | issue = 5 | pages = 350–361 | date = October 2005 | pmid = 15979209 | doi = 10.1016/j.neuint.2005.04.026 | s2cid = 23372945 }}</ref><ref>{{cite journal | vauthors = Jaehne EJ, Salem A, Irvine RJ | title = Pharmacological and behavioral determinants of cocaine, methamphetamine, 3,4-methylenedioxymethamphetamine, and para-methoxyamphetamine-induced hyperthermia | journal = Psychopharmacology | volume = 194 | issue = 1 | pages = 41–52 | date = September 2007 | pmid = 17530474 | doi = 10.1007/s00213-007-0825-9 | s2cid = 25420902 }}</ref> 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.<ref>{{cite journal | vauthors = Refstad S | title = Paramethoxyamphetamine (PMA) poisoning; a 'party drug' with lethal effects | journal = Acta Anaesthesiologica Scandinavica | volume = 47 | issue = 10 | pages = 1298–1299 | date = November 2003 | pmid = 14616331 | doi = 10.1046/j.1399-6576.2003.00245.x | s2cid = 28006785 | doi-access = free }}</ref>

==Chemistry== ===Synthesis=== The chemical synthesis of PMA has been described.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" />

===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.<ref name="PiHKAL" /><ref name="ShulginManningDaley2011" /> Anisomycin contains PMA within its chemical structure.

==History== PMA was first described in the scientific literature by T. Patrick and colleagues by 1946.<ref name="PatrickMcBeeHass">{{cite journal | vauthors = Patrick TM, McBee ET, Hass HB | title = Synthesis of arylpropylamines; from allyl chloride | journal = J Am Chem Soc | volume = 68 | issue = | pages = 1009–1011 | date = June 1946 | pmid = 20985610 | doi = 10.1021/ja01210a032 | url = }}</ref> 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.<ref name="PiHKAL"/> 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.<ref>{{cite web |url = http://www.erowid.org/chemicals/pma/pma_dea_intellbrief.pdf |title = The Hallucinogen PMA: Dancing With Death |access-date = 2008-06-29 |author = DEA |archive-date = 2008-06-23 |archive-url = https://web.archive.org/web/20080623010031/http://www.erowid.org/chemicals/pma/pma_dea_intellbrief.pdf |url-status = live }}</ref> Between 1974 and the mid-1990s, there appear to have been no known fatalities from PMA.<ref>{{cite journal | vauthors = Felgate HE, Felgate PD, James RA, Sims DN, Vozzo DC | title = Recent paramethoxyamphetamine deaths | journal = Journal of Analytical Toxicology | volume = 22 | issue = 2 | pages = 169–172 | date = 1 March 1998 | pmid = 9547415 | doi = 10.1093/jat/22.2.169 | doi-access = free }}</ref>

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.<ref name="pmid9760094" /> There have been a number of PMA-induced deaths around the world since then.<ref name="pmid15274949">{{cite journal | vauthors = Galloway JH, Forrest AR | title = Caveat Emptor: Death involving the use of 4-methoxyamphetamine | journal = Journal of Clinical Forensic Medicine | volume = 9 | issue = 3 | pages = 160 | date = September 2002 | pmid = 15274949 | doi = 10.1016/S1353-1131(02)00043-3 }}</ref><ref name="pmid18393753">{{cite journal | vauthors = Lamberth PG, Ding GK, Nurmi LA | title = Fatal paramethoxy-amphetamine (PMA) poisoning in the Australian Capital Territory | journal = The Medical Journal of Australia | volume = 188 | issue = 7 | pages = 426 | date = April 2008 | pmid = 18393753 | doi = 10.5694/j.1326-5377.2008.tb01695.x | s2cid = 11987961 }}</ref>

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.<ref name="fake-ecstasy-warning-die-scotland" /> Several deaths in Northern Ireland, Particularly East Belfast, were also linked to "Green Rolex" pills during that month.<ref>{{cite news|url=https://www.bbc.com/news/uk-northern-ireland-23440537|title=Renewed warning over 'Rolex' pills|date=24 July 2013|work=BBC News|access-date=10 September 2018|archive-date=11 September 2018|archive-url=https://web.archive.org/web/20180911053120/https://www.bbc.com/news/uk-northern-ireland-23440537|url-status=live}}</ref>

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.<ref name=Barrell2015/><ref>{{cite web|url=http://www.deephouseamsterdam.com/watch-out-for-dangerous-superman-pill/|title=WATCH OUT FOR DANGEROUS SUPERMAN PILL - News - Deep House Amsterdam|date=30 January 2014|website=deephouseamsterdam.com|access-date=2 January 2015|archive-date=2 January 2015|archive-url=https://web.archive.org/web/20150102182954/http://www.deephouseamsterdam.com/watch-out-for-dangerous-superman-pill/|url-status=live}}</ref><ref>{{cite web | url = http://www.elpais.com.uy/mundo/superman-droga-que-mezcla-metanfetamina-extasis.html | title = ¿Qué es Superman, la droga que ya ha cobrado varias vidas en el mundo? | trans-title = What is Superman, the drug that has already claimed several lives in the world? | language = Spanish | work = ElPais | date = 18 April 2016 | trans-work = The Country | access-date = 19 April 2016 | archive-date = 19 April 2016 | archive-url = https://web.archive.org/web/20160419162910/http://www.elpais.com.uy/mundo/superman-droga-que-mezcla-metanfetamina-extasis.html | url-status = live }}</ref><ref>{{cite news|url=http://www.lanacion.com.ar/1890180-las-claves-para-entender-que-paso|title=Las claves para entender qué pasó|date=2016-04-17|newspaper=La Nación|access-date=2016-04-19|archive-date=2016-04-18|archive-url=https://web.archive.org/web/20160418210708/http://www.lanacion.com.ar/1890180-las-claves-para-entender-que-paso|url-status=live}}</ref>

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.<ref>{{cite web|url=https://www.reagent-tests.uk/blog/category/drug-warning/|title=Drug Warning – Reagent Tests UK|website=www.reagent-tests.uk|access-date=2017-07-05|archive-date=2018-09-11|archive-url=https://web.archive.org/web/20180911045132/https://www.reagent-tests.uk/blog/category/drug-warning/|url-status=live}}</ref>

==Society and culture== ===Legal status=== ====International==== PMA is a Schedule I drug under the Convention on Psychotropic Substances.<ref>{{cite web |url = http://www.incb.org/pdf/e/list/green.pdf |title = Annual Estimates Of Requirements Of Narcotic Drugs, Manufacture Of Synthetic Drugs, Opium Production And Cultivation Of The… |access-date = 2008-06-15 |archive-date = 2012-08-31 |archive-url = https://web.archive.org/web/20120831222336/http://www.incb.org/pdf/e/list/green.pdf |url-status = dead }}</ref>

====Australia==== PMA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).<ref name="Poisons Standard">Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534 {{Webarchive|url=https://web.archive.org/web/20160119074606/https://www.comlaw.gov.au/Details/F2015L01534/ |date=2016-01-19 }}</ref> 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.<ref name="Poisons Standard" />

====Canada==== PMA is a Schedule I controlled substance in Canada.<ref name="CDSA2025">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | date=5 December 2025 | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=20 January 2026}}</ref>

====Finland==== Substance is scheduled in decree of the substances, preparations and plants considered to be narcotic drugs.<ref>{{cite web | title = Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista annetun valtioneuvoston asetuksen muuttamisesta | trans-title = Decree of the Government on amending the government decree on substances, preparations and plants considered to be narcotic drugs | work = Finlex | publisher = Finland's Ministry of Justice | location = Helsinki | date = 25 October 2018 | language = Finnish | url = https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2018/839 | access-date = 8 April 2023 | archive-date = 26 March 2023 | archive-url = https://web.archive.org/web/20230326140527/https://www.finlex.fi/fi/laki/alkup/2018/20180839 | url-status = live }}</ref><ref>{{cite web | title = Valtioneuvoston asetus huumausaineina pidettävistä aineista, valmisteista ja kasveista annetun valtioneuvoston asetuksen muuttamisesta | trans-title = Decree of the Government on amending the government decree on substances, preparations and plants considered to be narcotic drugs | work = Finlex | publisher = Finland's Ministry of Justice | location = Helsinki | date = 13 January 2022 | language = Finnish | url = https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2022/13 | access-date = 8 April 2023 | archive-date = 24 March 2023 | archive-url = https://web.archive.org/web/20230324040740/https://www.finlex.fi/fi/laki/alkup/2022/20220013 | url-status = live }}</ref>

====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.<ref>{{cite web |url=http://nos.nl/artikel/383346-schippers-verbiedt-dodelijk-4ma.html |title=Doden na gebruik speed met 4-MA |trans-title=Deaths after using speed 4-MA |date=13 June 2012 |language=nl |access-date=13 June 2012 |archive-date=16 June 2012 |archive-url=https://web.archive.org/web/20120616014616/http://nos.nl/artikel/383346-schippers-verbiedt-dodelijk-4ma.html |url-status=live }}</ref>

====United Kingdom==== PMA is a Class A drug in the UK.<ref>{{Cite web |date=2013-08-13 |title=List of Controlled Drugs |url=https://www.release.org.uk/law/list-controlled-drugs |access-date=2024-04-29 |website=Release (agency) |language=en |archive-date=2024-04-29 |archive-url=https://web.archive.org/web/20240429141724/https://www.release.org.uk/law/list-controlled-drugs |url-status=live }}</ref>

====United States==== PMA is classified as a Schedule I hallucinogen under the Controlled Substances Act in the United States.<ref>21 CFR [http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm 1308.11] {{Webarchive|url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |date=2009-08-27 }}</ref>

===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.<ref>{{cite journal | vauthors = Galloway JH, Forrest AR | title = Caveat Emptor: Death involving the use of 4-methoxyamphetamine | journal = Journal of Clinical Forensic Medicine | volume = 9 | issue = 3 | pages = 160 | date = September 2002 | pmid = 15274949 | doi = 10.1016/s1353-1131(02)00043-3 }}</ref> 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.<ref>{{cite web|url = http://dancesafe.org/documents/druginfo/pma_faq.php |title = Drug Info |access-date = 2008-06-15 |archive-url = https://web.archive.org/web/20080529024316/http://www.dancesafe.org/documents/druginfo/pma_faq.php  |archive-date = 2008-05-29}}</ref><ref>{{cite web |url = http://ecstasy.org/testing/pma.html |title = Warning: pills sold as ecstasy found to contain PMA |access-date = 2008-06-15 |archive-date = 2008-06-22 |archive-url = https://web.archive.org/web/20080622205340/http://ecstasy.org/testing/pma.html |url-status = live }}</ref> Notable batches of pills containing PMA have included Louis Vuitton,<ref>Chamberlin T, Murray D. NET Syndicated QLD News [http://www.news.com.au/national/louis-vuitton-designer-death-drug-hits-the-streets/story-fndo4ckr-1226463080805 'Louis Vuitton' designer death drug hits the streets] {{Webarchive|url=https://web.archive.org/web/20120928235358/http://www.news.com.au/national/louis-vuitton-designer-death-drug-hits-the-streets/story-fndo4ckr-1226463080805 |date=2012-09-28 }}</ref> Mitsubishi Turbo, Blue Transformers, Red/Blue Mitsubishi and Yellow Euro pills. Also PMA has been found in powder form.<ref>{{cite journal | vauthors = Kraner JC, McCoy DJ, Evans MA, Evans LE, Sweeney BJ | title = Fatalities caused by the MDMA-related drug paramethoxyamphetamine (PMA) | journal = Journal of Analytical Toxicology | volume = 25 | issue = 7 | pages = 645–648 | date = October 2001 | pmid = 11599617 | doi = 10.1093/jat/25.7.645 | doi-access = free }}</ref>

====Analogues==== Four analogues of PMA have been reported to be sold on the black market, including PMMA, PMEA,<ref>{{cite journal | vauthors = Casale JF, Hays PA, Spratley TK, Smith PR |title=The Characterization of 4-Methoxy-N-ethylamphetamine Hydrochloride |journal=Microgram Journal |year=2006 |volume=4 |issue=1–4 |pages=42–46 }}</ref> 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.<ref name="PiHKAL"/> 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".<ref name="Aipsin">{{cite web | title=Мебеверин (Mebeverine) | website=АИПСИН | url=https://aipsin.com/newsubstance/333/ | language=ru | access-date=2 January 2026}}</ref>

==References== {{Reflist}}

==External links== {{Commons category}} * [https://isomerdesign.com/pihkal/explore/97 PMA - Isomer Design] * [https://psychonautwiki.org/wiki/PMA PMA - PsychonautWiki] * [https://www.erowid.org/chemicals/pma/pma.shtml PMA - Erowid] * [https://www.erowid.org/library/books_online/pihkal/pihkal097.shtml 4-MA (PMA) - PiHKAL - Isomer Design] * [https://isomerdesign.com/pihkal/read/pk/97 4-MA (PMA) - PiHKAL - Isomer Design] * [https://archive.org/details/shulgin-index-vol-1/page/267/mode/1up?view=theater PMA (4-MA) - The Shulgin Index]

{{Psychedelics}} {{Monoamine releasing agents}} {{Serotonin receptor modulators}} {{Monoamine metabolism modulators}} {{TAAR modulators}} {{Phenethylamines}}

Category:Designer drugs Category:Methoxyphenethylamines Category:4-Methoxyphenyl compounds Category:Monoamine oxidase inhibitors Category:PiHKAL Category:Psychedelic phenethylamines Category:Serotonin receptor agonists Category:Serotonin releasing agents Category:Substituted amphetamines Category:TAAR1 modulators