{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = PeMA | image = Pentamethoxyamphetamine.svg | image_class = skin-invert-image | width = 225px | caption =
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<!-- Identifiers --> | CAS_number = 23693-29-0 | CAS_supplemental = | PubChem = 129681609 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = PeMA; 2,3,4,5,6-Pentamethoxyamphetamine; 2,3,4,5,6-PeMA; 2,6-Dimethoxy-TMA; 3,6-Dimethoxy-TMA-2
<!-- Chemical data --> | IUPAC_name = 1-(2,3,4,5,6-pentamethoxyphenyl)propan-2-amine | C=14 | H=23 | N=1 | O=5 | SMILES = CC(CC1=C(C(=C(C(=C1OC)OC)OC)OC)OC)N | StdInChI = 1S/C14H23NO5/c1-8(15)7-9-10(16-2)12(18-4)14(20-6)13(19-5)11(9)17-3/h8H,7,15H2,1-6H3 | StdInChIKey = CDUJLDXLXICILS-UHFFFAOYSA-N }}
'''Pentamethoxyamphetamine''' ('''PeMA'''), also known as '''2,3,4,5,6-pentamethoxyamphetamine''' ('''2,3,4,5,6-PeMA'''), '''2,6-dimethoxy-TMA''', or '''3,6-dimethoxy-TMA-2''', is a chemical compound of the phenethylamine and amphetamine families related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine).<ref name="Shulgin_2011">{{cite book | vauthors = Shulgin A, Manning T, Daley PF | chapter = #108. PeMPEA | title = The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | location = Berkeley, CA | volume = 1 | pages = 263–264 | year = 2011 | chapter-url = https://archive.org/details/shulgin-index-vol-1/page/263/mode/1up | publisher = Transform Press | isbn = 978-0-9630096-3-0 | oclc = 709667010 }}</ref><ref name="Shulgin_1969">{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = Structure–Activity Relationships of One-Ring Psychotomimetics | journal = Nature | volume = 221 | issue = 5180 | pages = 537–541 | date = 1969 | pmid = 5789297 | doi = 10.1038/221537a0 | issn = 0028-0836 | url = https://www.nature.com/articles/221537a0 | url-access = subscription }}</ref> It is the α-methyl or amphetamine derivative of pentamethoxyphenethylamine (PeMPEA).<ref name="Shulgin_2011" /><ref name="Shulgin_1969" /> The compound does not seem to have been tested in animals or humans.<ref name="Shulgin_2011" /><ref name="Shulgin_1969" /> However, the related drug PeMPEA is known to be behaviorally active in animal studies.<ref name="Shulgin_2011" /><ref name="Brimblecombe_1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Phenylalkylamines and Their Derivatives | title = Hallucinogenic Agents | location = Bristol | pages = 55–97 | date = 1975 | publisher = Wright-Scientechnica | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = Table 3.2.—Relative Hallucinogenic Potencies of Some Phenylethylamines [...] }}</ref> PeMA was first described in the scientific literature by Alexander Shulgin by 1969.<ref name="Shulgin_1969" /> It is a controlled substance in Canada under phenethylamine blanket-ban language.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
==See also== * Substituted methoxyphenethylamine * Pentamethoxyphenethylamine * Tetramethoxyamphetamine * Tetramethoxyphenethylamine * Trimethoxyamphetamine * Dimethoxymethylenedioxyamphetamine * DOTMA
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/7914 PeMA - Isomer Design]
{{Phenethylamines}}
Category:3C (psychedelics) Category:DOx (psychedelics) Category:Methoxyphenethylamines
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