{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = PeMPEA | image = Pentamethoxyphenethylamine.svg | image_class = skin-invert-image | width = 225px | caption =
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<!-- Identifiers --> | CAS_number = | CAS_supplemental = | PubChem = 618053 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 537125 | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = PeMPEA; 2,3,4,5,6-Pentamethoxyphenethylamine; 2,3,4,5,6-PeMPEA; 2,6-Dimethoxymescaline; 2,6-Dimethoxy-TMPEA; 3,6-Dimethoxy-2C-O; 3,6-Dimethoxy-TMPEA-2
<!-- Chemical data --> | IUPAC_name = 2-(2,3,4,5,6-pentamethoxyphenyl)ethanamine | C=13 | H=21 | N=1 | O=5 | SMILES = COC1=C(C(=C(C(=C1OC)OC)OC)OC)CCN | StdInChI = 1S/C13H21NO5/c1-15-9-8(6-7-14)10(16-2)12(18-4)13(19-5)11(9)17-3/h6-7,14H2,1-5H3 | StdInChIKey = SRUXXIUKHPJJRC-UHFFFAOYSA-N }}
'''Pentamethoxyphenethylamine''' ('''PeMPEA'''), also known as '''2,3,4,5,6-pentamethoxyphenethylamine''' ('''2,3,4,5,6-PeMPEA''') or as '''2,6-dimethoxymescaline''', is a drug of the phenethylamine family 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="Brimblecombe_1975" />
It has been found to produce behavioral effects in animals, with about 8-fold higher potency than mescaline in the conditioned avoidance response test.<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><ref name="Glennon_1979">{{cite journal | vauthors = Glennon RA, Kier LB, Shulgin AT | title = Molecular connectivity analysis of hallucinogenic mescaline analogs | journal = Journal of Pharmaceutical Sciences | volume = 68 | issue = 7 | pages = 906–907 | date = July 1979 | pmid = 458614 | doi = 10.1002/jps.2600680733 | quote = Previous investigators (a), employing a modified Bovet-Gatti profile, found that 2,3,4,5,6-pentamethoxyphenethylamine (XIII) is behaviorally active in animal models with a potency about eight times that of mescaline. With the relating equation, XIII is predicted to have a potency of ~4.5 mescaline units. }}</ref><ref name="Smythies_1967">{{cite journal | vauthors = Smythies JR, Bradley RJ, Johnston VS, Benington F, Morin RD, Clark LC | title = Structure-activity relationship studies on mescaline. 3. The influence of the methoxy groups | journal = Psychopharmacologia | volume = 10 | issue = 5 | pages = 379–387 | date = 1967 | pmid = 5588333 | doi = 10.1007/BF00403978 }}</ref><ref name="Clark_1964">{{cite journal | vauthors = Clark LC, Benington F, Morin RD | title = The enzymatic oxidative deamination and effect on cat behavior mescaline and structurally-related beta-phenethylamines | journal = The Alabama Journal of Medical Sciences | volume = 1 | pages = 417–429 | date = October 1964 | pmid = 14230671 }}</ref> The pharmacokinetics of the drug in rodents have been studied.<ref name="Cohen_1974">{{cite journal | vauthors = Cohen I, Fischer JF, Vogel WH | title = Physiological disposition of beta-phenylethylamine, 2,4,5-trimethoxyphenylethylamine, 2,3,4,5,6-pentamethoxyphenylethylamine and beta-hydroxymescaline in rat brain, liver and plasma | journal = Psychopharmacologia | volume = 36 | issue = 1 | pages = 77–84 | date = March 1974 | pmid = 4838506 | doi = 10.1007/BF00441384 }}</ref> The effects of PeMPEA in humans have not been reported and are unknown.<ref name="Shulgin_2011" /><ref name="Brimblecombe_1975" />
It was first described in the scientific literature by 1955.<ref name="Shulgin_2011" /><ref name="Benington_1955">{{cite journal | vauthors = Benington F, Morin RD, Clark LC | title = Mescaline Analogs. II. Tetra- and Penta-Methoxy-Βeta-Phenethylamines | journal = The Journal of Organic Chemistry | volume = 20 | issue = 1 | pages = 102–108 | date = 1955 | doi = 10.1021/jo01119a017 | issn = 0022-3263 | url = https://pubs.acs.org/doi/abs/10.1021/jo01119a017 | access-date = 3 July 2025 | url-access = subscription }}</ref> PeMPEA was included as an entry in Alexander Shulgin's 2011 book ''The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds''.<ref name="Shulgin_2011" /> 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 * Pentamethoxyamphetamine (PeMA) * Tetramethoxyphenethylamine * 2,3,4,5-Tetramethoxyphenethylamine (TeMPEA) * 2,3,4,5-Tetramethoxyamphetamine (TeMA) * Dimethoxymethylenedioxyamphetamine (DMMDA) * 2,6-Dimethylmescaline * 2,6-Dibromomescaline * 2,6-Dichloromescaline
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/453 PeMPEA - Isomer Design]
{{Phenethylamines}}
Category:2C (psychedelics) Category:Methoxyphenethylamines Category:Scalines
{{Hallucinogen-stub}}