Editing Para-Methoxyamphetamine (section)

{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Distinguish|4-methylamphetamine|4-MA steroid}}
{{Infobox drug
| Verifiedfields = changed
| verifiedrevid = 461747299
| drug_name = ''para''-Methoxyamphetamine
| image = PMA.svg
| image_class = skin-invert-image
| width = 150px
| image2 = 4-Methoxyamphetamine_molecule_ball.png
| width2 = 150px

<!--Clinical data-->
| tradename = 
| pregnancy_category = 
| routes_of_administration = [[By mouth]]
| class = [[Selective serotonin releasing agent]] (SSRA); [[Serotonergic psychedelic]]
| ATC_prefix = None
| ATC_suffix = 

<!--Legal status-->
| 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 that was for medical, therapeutic or scientific use.

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 

<!--Identifiers-->
| 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

<!--Chemical data-->
| 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 [[substituted amphetamine|amphetamine]] class with [[Serotonin|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="Alexander & Ann Shulgin, PiHKAL #97">{{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 [[entactogen]] 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 drug|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 [[Tablet (pharmacy)|tablets]] touted 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 flavor compound of [[anise]] and [[fennel]], mainly because the starting material for MDMA, [[safrole]], has become less available due to law enforcement action, causing illicit drug manufacturers to use anethole 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>