2,3,4,6-Tetramethoxyphenethylamine

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'''2,3,4,6-Tetramethoxyphenethylamine''' ('''2,3,4,6-TeMPEA'''), also known as '''TeMPEA-2''', is a [[drug]] of the [[substituted phenethylamine|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 = #115. TeMPEA-3 | title = [[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]] | location = Berkeley, CA | volume = 1 | pages = 282–283 | year = 2011 | chapter-url = https://archive.org/details/shulgin-index-vol-1/page/282/mode/1up | publisher = Transform Press | isbn = 978-0-9630096-3-0 | oclc = 709667010 }}</ref><ref name="Trachsel_2013">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title = Phenethylamine: von der Struktur zur Funktion | location = Solothurn | pages = 883,923 | year = 2013 | trans-title = Phenethylamines: From Structure to Function | edition = 1 | publisher = Nachtschatten-Verlag | series = Nachtschatten-Science | isbn = 978-3-03788-700-4 | oclc = 858805226 | url = https://books.google.com/books?id=-Us1kgEACAAJ | language = de }}</ref> It is one of the possible [[positional isomer]]s of [[tetramethoxyphenethylamine]] (TeMPEA).<ref name="Shulgin_2011" /><ref name="Trachsel_2013" /> The ''[[in-vitro]]'' [[drug metabolism|metabolism]] and effects of TeMPEA-2 on behavior in animals have been studied.<ref name="Shulgin_2011" /><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 β-phenethylamines | journal = The Alabama Journal of Medical Sciences | volume = 1 | pages = 417–429 | date = October 1964 | pmid = 14230671 }}</ref><ref name="Clark_1965">{{cite journal | vauthors = Clark LC, Benington F, Morin RD | title = The effects of ring-methoxyl groups on biological deamination of phenethylamines | journal = Journal of Medicinal Chemistry | volume = 8 | issue = 3 | pages = 353–355 | date = May 1965 | pmid = 14323146 | doi = 10.1021/jm00327a016 }}</ref> The drug showed little or no activity as a [[norepinephrine releasing agent]] ''in vitro''.<ref name="Shulgin_2011" /><ref name="Daly_1966">{{cite journal | vauthors = Daly JW, Creveling CR, Witkop B | title = The chemorelease of norepinephrine from mouse hearts. Structure-activity relationships. I. Sympathomimetic and related amines | journal = Journal of Medicinal Chemistry | volume = 9 | issue = 3 | pages = 273–280 | date = May 1966 | pmid = 5960887 | doi = 10.1021/jm00321a001 }}</ref> It does not seem to have been tested in humans.<ref name="Shulgin_2011" /> TeMPEA-2 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-β-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 }}</ref>

'''2,3,4,6-Tetramethoxyphenethylamine''' ('''2,3,4,6-TeMPEA'''), also known as '''TeMPEA-2''', is a [[drug]] of the [[substituted phenethylamine|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 = #115. TeMPEA-3 | title = [[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]] | location = Berkeley, CA | volume = 1 | pages = 282–283 | year = 2011 | chapter-url = https://archive.org/details/shulgin-index-vol-1/page/282/mode/1up | publisher = Transform Press | isbn = 978-0-9630096-3-0 | oclc = 709667010 }}</ref><ref name="Trachsel_2013">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title = Phenethylamine: von der Struktur zur Funktion | location = Solothurn | pages = 883, 923 | year = 2013 | trans-title = Phenethylamines: From Structure to Function | edition = 1 | publisher = Nachtschatten-Verlag | series = Nachtschatten-Science | isbn = 978-3-03788-700-4 | oclc = 858805226 | url = https://books.google.com/books?id=-Us1kgEACAAJ | language = de }}</ref> It is one of the possible [[positional isomer]]s of [[tetramethoxyphenethylamine]] (TeMPEA).<ref name="Shulgin_2011" /><ref name="Trachsel_2013" /> The ''[[in-vitro]]'' [[drug metabolism|metabolism]] and effects of TeMPEA-2 on behavior in animals have been studied.<ref name="Shulgin_2011" /><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 β-phenethylamines | journal = The Alabama Journal of Medical Sciences | volume = 1 | pages = 417–429 | date = October 1964 | pmid = 14230671 }}</ref><ref name="Clark_1965">{{cite journal | vauthors = Clark LC, Benington F, Morin RD | title = The effects of ring-methoxyl groups on biological deamination of phenethylamines | journal = Journal of Medicinal Chemistry | volume = 8 | issue = 3 | pages = 353–355 | date = May 1965 | pmid = 14323146 | doi = 10.1021/jm00327a016 }}</ref> The drug showed little or no activity as a [[norepinephrine releasing agent]] ''in vitro''.<ref name="Shulgin_2011" /><ref name="Daly_1966">{{cite journal | vauthors = Daly JW, Creveling CR, Witkop B | title = The chemorelease of norepinephrine from mouse hearts. Structure-activity relationships. I. Sympathomimetic and related amines | journal = Journal of Medicinal Chemistry | volume = 9 | issue = 3 | pages = 273–280 | date = May 1966 | pmid = 5960887 | doi = 10.1021/jm00321a001 }}</ref> It does not seem to have been tested in humans.<ref name="Shulgin_2011" /> TeMPEA-2 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-β-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 }}</ref>

==See also==

==See also==

==External links==

==External links==

* [https://isomerdesign.com/pihkal/explore/7873 TeMPEA-2 - Isomer Design]

* [https://isomerdesign.com/pihkal/explore/7873 TeMPEA-2 - Isomer Design]

{{Phenethylamines}}

{{Phenethylamines}}

[[Category:Methoxyphenethylamines]]

[[Category:Methoxyphenethylamines]]

{{Hallucinogen-stub}}

{{Hallucinogen-stub}}