# Pentamethoxyamphetamine

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{{Infobox drug
| drug_name = PeMA
| image = Pentamethoxyamphetamine.svg
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| width = 225px
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| CAS_number = 23693-29-0
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| PubChem = 129681609
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| 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](/source/chemical_compound) of the [phenethylamine](/source/substituted_phenethylamine) and [amphetamine](/source/substituted_amphetamine) families related to the [psychedelic drug](/source/psychedelic_drug) [mescaline](/source/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](/source/The_Shulgin_Index%2C_Volume_One%3A_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](/source/methyl_group) or amphetamine [derivative](/source/chemical_derivative) of [pentamethoxyphenethylamine](/source/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](/source/animal_study).<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](/source/scientific_literature) by [Alexander Shulgin](/source/Alexander_Shulgin) by 1969.<ref name="Shulgin_1969" /> It is a [controlled substance](/source/controlled_substance) in [Canada](/source/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](/source/Substituted_methoxyphenethylamine)
* [Pentamethoxyphenethylamine](/source/Pentamethoxyphenethylamine)
* [Tetramethoxyamphetamine](/source/Tetramethoxyamphetamine)
* [Tetramethoxyphenethylamine](/source/Tetramethoxyphenethylamine)
* [Trimethoxyamphetamine](/source/Trimethoxyamphetamine)
* [Dimethoxymethylenedioxyamphetamine](/source/Dimethoxymethylenedioxyamphetamine)
* [DOTMA](/source/DOTMA)

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/7914 PeMA - Isomer Design]

{{Phenethylamines}}

Category:3C (psychedelics)
Category:DOx (psychedelics)
Category:Methoxyphenethylamines

{{Nervous-system-drug-stub}}

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Adapted from the Wikipedia article [Pentamethoxyamphetamine](https://en.wikipedia.org/wiki/Pentamethoxyamphetamine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Pentamethoxyamphetamine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.