# Meta-DOT

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Meta-DOT
> Markdown URL: https://mediated.wiki/source/Meta-DOT.md
> Source: https://en.wikipedia.org/wiki/Meta-DOT
> Source revision: 1340340232
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{Infobox drug
| verifiedrevid = 415699350
| drug_name = 
| image = Meta-DOT.svg
| image_class = skin-invert-image
| width = 225px
| caption = 

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| pronounce = 
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| pregnancy_AU = 
| pregnancy_category = 
| dependency_liability = 
| addiction_liability = 
| 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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| legal_status = 

<!-- Pharmacokinetic data -->
| bioavailability = 
| protein_bound = 
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| elimination_half-life = 
| duration_of_action = Unknown<ref name="PiHKAL" />
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<!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 79440-52-1
| CAS_supplemental = 
| PubChem = 144891
| PubChemSubstance = 
| IUPHAR_ligand = 
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 127832
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8A89CW1FXK
| KEGG = 
| ChEBI = 
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 31787
| NIAID_ChemDB = 
| PDB_ligand = 
| synonyms = 5-Methylthio-2,4-dimethoxyamphetamine; 2,4-Dimethoxy-5-methylthioamphetamine; 5-Thio-TMA-2

<!-- Chemical data -->
| IUPAC_name = 1-[2,4-dimethoxy-5-(methylsulfanyl)phenyl]propan-2-amine
| C = 12 | H = 19 | N = 1 | O = 2 | S = 1
| SMILES = O(c1cc(OC)c(cc1SC)CC(N)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H19NO2S/c1-8(13)5-9-6-12(16-4)11(15-3)7-10(9)14-2/h6-8H,5,13H2,1-4H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BEMIKIUJWHLJTP-UHFFFAOYSA-N
}}

'''Meta-DOT''', also known as '''5-methylthio-2,4-dimethoxyamphetamine''' or as '''5-thio-TMA-2''', is a [psychoactive drug](/source/psychoactive_drug) of the [phenethylamine](/source/substituted_phenethylamine) and [amphetamine](/source/substituted_amphetamine) families related to [TMA-2](/source/TMA-2_(drug)).<ref name="PiHKAL">{{CitePiHKAL}} http://www.erowid.org/library/books_online/pihkal/pihkal125.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 | quote = The two other possible oxygen substitutions of DOT have been synthesized and evaluated; this completes the three theoretical thio-analogues of TMA-2. 4,5-Dimethoxy-2-methylthioamphetamine and 2,4-dimethoxy-5-methylthioam-phetamine (Ortho-DOT and Meta-DOT respectively) were without any central effects at levels of 25mg orally.}}</ref> It is the [analogue](/source/structural_analog) of TMA-2 in which the [methoxy group](/source/methoxy_group) at the 5 position has been replaced with a [methylthio group](/source/methylthio_group).<ref name="PiHKAL" /><ref name="Shulgin2003" /> In addition, the drug is a [positional isomer](/source/positional_isomer) of [Aleph](/source/Aleph_(psychedelic)) (DOT; para-DOT).<ref name="PiHKAL" /><ref name="Shulgin2003" />

In his book ''[PiHKAL](/source/PiHKAL)'' (''Phenethylamines I Have Known and Loved'') and other publications, [Alexander Shulgin](/source/Alexander_Shulgin) lists meta-DOT's dose as greater than 35{{nbsp}}mg [orally](/source/oral_administration) and its [duration](/source/duration_of_action) as unknown.<ref name="PiHKAL" /><ref name="Shulgin2003" /> The effects of meta-DOT have been reported to include threshold effects, a vague awareness of something or of a "thinness", and possibly some brief [cardiovascular](/source/cardiovascular) [stimulation](/source/sympathomimetic).<ref name="PiHKAL" /> However, the effects at tested doses were not said to be completely believable and Shulgin concluded that it was inactive.<ref name="PiHKAL" /><ref name="Shulgin2003" /> Higher doses were not tested.<ref name="PiHKAL" />

Meta-DOT has been found to produce [hyperthermia](/source/hyperthermia) in rabbits, albeit with approximately 30-fold lower [potency](/source/potency_(pharmacology)) than [DOM](/source/DOM_(drug)), though with somewhat greater potency than [mescaline](/source/mescaline).<ref name="PiHKAL" /><ref name="JacobAndersonMeshul1977" />

The [chemical synthesis](/source/chemical_synthesis) of meta-DOT has been described.<ref name="PiHKAL" /><ref name="JacobAndersonMeshul1977" /> Analogues of meta-DOT include TMA-2, Aleph (DOT; para-DOT; 4-thio-TMA-2), [ortho-DOT](/source/ortho-DOT) (2-thio-TMA-2), [5-TOM](/source/5-TOM) (5-thio-DOM), and [5-TOET](/source/5-TOET) (5-thio-DOET), among others.<ref name="PiHKAL" /><ref name="Shulgin2003" />

Meta-DOT was first described in the [scientific literature](/source/scientific_literature) by Shulgin and colleagues in 1977.<ref name="JacobAndersonMeshul1977">{{cite journal | vauthors = Jacob P, Anderson G, Meshul CK, Shulgin AT, Castagnoli N | title = Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane | journal = J Med Chem | volume = 20 | issue = 10 | pages = 1235–1239 | date = October 1977 | pmid = 903913 | doi = 10.1021/jm00220a001 | url = https://bibliography.maps.org/resources/download/8601 | archive-url = https://web.archive.org/web/20250712230051/https://bibliography.maps.org/resources/download/8601 | archive-date = 2025-07-12}}</ref> Subsequently, it was described in greater detail by Shulgin in ''PiHKAL'' in 1991.<ref name="PiHKAL" />

==See also==
* [Substituted methoxyphenethylamine](/source/Substituted_methoxyphenethylamine)
* [DOx § Related compounds](/source/DOx)
* [Meta-DOB](/source/Meta-DOB) (5-bromo-TMA-2)

==References==
{{Reflist}}

==External links==
* [https://isomerdesign.com/pihkal/explore/125 META-DOT - Isomer Design]
* [https://erowid.org/library/books_online/pihkal/pihkal125.shtml META-DOT - PiHKAL - Erowid]
* [https://isomerdesign.com/pihkal/read/pk/125 META-DOT - PiHKAL - Isomer Design]

{{Phenethylamines}}

Category:Methoxyphenethylamines
Category:Methylthio compounds
Category:PiHKAL
Category:Psychoactive drugs
Category:Substituted amphetamines
Category:Thio-2Cs and -DOx

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