# 2-TOET

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/2-TOET
> Markdown URL: https://mediated.wiki/source/2-TOET.md
> Source: https://en.wikipedia.org/wiki/2-TOET
> Source revision: 1338619885
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Infobox drug
| drug_name = 
| image = 2-TOET.svg
| image_class = skin-invert-image
| width = 225px
| caption = 

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| dependency_liability = 
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| routes_of_administration = [Oral](/source/Oral_administration)<ref name="PiHKAL" />
| class = [Psychoactive drug](/source/Psychoactive_drug)
| ATC_prefix = None
| ATC_suffix = 

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<!-- Pharmacokinetic data -->
| bioavailability = 
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| duration_of_action = Unknown (but long-lasting)<ref name="PiHKAL" />
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<!-- Identifiers -->
| CAS_number = 779279-63-9
| CAS_supplemental = 
| PubChem = 15915347
| PubChemSubstance = 
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| ChemSpiderID = 21106408
| UNII = 28GRS3DSL2
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| synonyms = 2-Methylthio-4-ethyl-5-methoxyamphetamine; 4-Ethyl-2-methylthio-5-methoxyamphetamine; 2-Thio-DOET; 2T-DOET; 2-Methylthio-DOET

<!-- Chemical data -->
| IUPAC_name = 1-(4-ethyl-5-methoxy-2-methylsulfanylphenyl)propan-2-amine
| C=13 | H=21 | N=1 | O=1 | S=1
| SMILES = CCC1=CC(=C(C=C1OC)CC(C)N)SC
| StdInChI = 1S/C13H21NOS/c1-5-10-8-13(16-4)11(6-9(2)14)7-12(10)15-3/h7-9H,5-6,14H2,1-4H3
| StdInChIKey = TZIBUOSWJBKVTA-UHFFFAOYSA-N
}}

'''2-TOET''', also known as '''2-methylthio-4-ethyl-5-methoxyamphetamine''' or as '''2-thio-DOET''', is a [psychoactive drug](/source/psychoactive_drug) of the [phenethylamine](/source/substituted_phenethylamine) and [amphetamine](/source/substituted_amphetamine) families related to the [DOx](/source/DOx_(psychedelics)) psychedelic [DOET](/source/DOET_(drug)).<ref name="PiHKAL">{{CitePiHKAL}} https://www.erowid.org/library/books_online/pihkal/pihkal169.shtml</ref><ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | veditors = Laing RR | chapter = Basic Pharmacology and Effects | title = Hallucinogens: A Forensic Drug Handbook | pages = 67–137 | year = 2003 | publisher = Elsevier Science | series = Forensic Drug Handbook Series | isbn = 978-0-12-433951-4 | url = https://books.google.com/books?id=l1DrqgobbcwC | chapter-url = https://bibliography.maps.org/resources/download/12634 | archive-url = https://web.archive.org/web/20250713013624/https://bibliography.maps.org/resources/download/12634 | archive-date = 13 July 2025 }}</ref><ref name="Nichols1994">{{cite book | vauthors = [Nichols DE](/source/David_E._Nichols) | veditors = Cho AK, Segal DS | chapter = Medicinal Chemistry and Structure-Activity Relationships | title = Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse | pages = 3–41 | date = 1994 | publisher = [Academic Press](/source/Academic_Press) | isbn = 978-0-12-173375-9 | url = https://books.google.com/books?id=w99sAAAAMAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/AmphetamineAndItsAnalogs3 | quote = Biological activity is low in compounds in which the oxygen atom of either the 2- or the 5-methoxy group has been replaced with a sulfur, illustrating the difficulty in developing bioisosteres of the 2,5-dimethoxy-substituted aromatic nucleus. However, if relative importance were assigned to the two methoxy groups, the 2-methoxy group would appear to be more, critical for optimal activity (Jacob et al., 1977). For example, referring to Table l, when the 2-methoxy group of DOEt is replaced with a methylthio group, in vivo activity is reduced by more than one order of magnitude (Jacob and Shulgin, 1983; Shulgin and Shulgin, 1991). However, the replacement of the 5-methoxy oxygen with a sulfur reduces activity only 4- to 6-fold. Similarly, when the 2-methoxy group of DOM is replaced with a methylthio group, activity drops by a factor of 10–20, whereas similar replacement of the 5-methoxy only reduces activity 5- to 10-fold (Jacob et al., 1977; Shulgin and Shulgin, 1991).}}</ref><ref name="JacobShulgin1983" /> It is the [analogue](/source/structural_analog) of DOET in which the [methoxy group](/source/methoxy_group) at the 2 position has been replaced with a [methylthio group](/source/methylthio_group).<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="Nichols1994" /><ref name="JacobShulgin1983" /> The drug is one of two possible [TOET](/source/TOET_(drug)) (thio-DOET) [positional isomer](/source/positional_isomer)s, the other being [5-TOET](/source/5-TOET).<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="Nichols1994" /><ref name="JacobShulgin1983" />

In his book ''[PiHKAL](/source/PiHKAL)'' (''Phenethylamines I Have Known and Loved'') and other publications, [Alexander Shulgin](/source/Alexander_Shulgin) lists 2-TOET's dose as greater than 65{{nbsp}}mg [orally](/source/oral_administration) and its [duration](/source/duration_of_action) as unknown (but long-lasting).<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="JacobShulgin1983" /> The drug is more than 10-fold less [potent](/source/potency_(pharmacology)) than DOET, which has a listed dose range of 2 to 6{{nbsp}}mg orally.<ref name="PiHKAL" /><ref name="Shulgin2003" /><ref name="Nichols1994" />

The effects of 2-TOET have been reported to include slight [lightheadedness](/source/lightheadedness), feeling physically a bit fragile, possible [appetite loss](/source/appetite_loss), possible [erectile dysfunction](/source/erectile_dysfunction), and next-day residual fragility.<ref name="PiHKAL" /> It was described as inactive as a [hallucinogen](/source/hallucinogen) at assessed doses, and higher doses were not tested.<ref name="PiHKAL" /><ref name="Shulgin2003" />

The [chemical synthesis](/source/chemical_synthesis) of 2-TOET has been described.<ref name="PiHKAL" /><ref name="JacobShulgin1983" /> The [phenethylamine](/source/substituted_phenethylamine) [analogue](/source/structural_analog), [2C-2-TOET](/source/2C-2-TOET) (2-thio-2C-E), has been synthesized, but was not tested and its properties are unknown.<ref name="PiHKAL" />

2-TOET was first described in the [scientific literature](/source/scientific_literature) by [Alexander Shulgin](/source/Alexander_Shulgin) and [Peyton Jacob III](/source/Peyton_Jacob_III) in 1983.<ref name="JacobShulgin1983">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Sulfur analogues of psychotomimetic agents. 2. Analogues of (2,5-dimethoxy-4-methylphenyl)-and (2,5-dimethoxy-4-ethylphenyl)isopropylamine | journal = J Med Chem | volume = 26 | issue = 5 | pages = 746–752 | date = May 1983 | pmid = 6842515 | doi = 10.1021/jm00359a021 | url = }}</ref> Subsequently, it was described in greater detail by Shulgin in ''PiHKAL'' in 1991.<ref name="PiHKAL" />

==See also==
* [Substituted methoxyphenethylamine](/source/Substituted_methoxyphenethylamine)
* [5-TOET](/source/5-TOET) and [2-TOM](/source/2-TOM)
* [Ortho-DOT](/source/Ortho-DOT) (2-thio-TMA-2)

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/169 2-TOET - Isomer Design]
* [https://erowid.org/library/books_online/pihkal/pihkal169.shtml 2-TOET - PiHKAL - Erowid]
* [https://isomerdesign.com/pihkal/read/pk/169 2-TOET - PiHKAL - Isomer Design]

{{Psychedelics}}
{{Phenethylamines}}

Category:Ethyl compounds
Category:Methoxyphenethylamines
Category:Methylthio compounds
Category:PiHKAL
Category:Psychedelic phenethylamines
Category:Substituted amphetamines
Category:Thio-2Cs and -DOx

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Adapted from the Wikipedia article [2-TOET](https://en.wikipedia.org/wiki/2-TOET) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/2-TOET?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.