{{Infobox drug | verifiedrevid = 415699350 | drug_name = | image = Meta-DOT.svg | image_class = skin-invert-image | width = 225px | caption =
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = Psychoactive drug | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = Unknown<ref name="PiHKAL" /> | excretion =
<!-- 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 of the phenethylamine and amphetamine families related to TMA-2.<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 of TMA-2 in which the methoxy group at the 5 position has been replaced with a methylthio group.<ref name="PiHKAL" /><ref name="Shulgin2003" /> In addition, the drug is a positional isomer of Aleph (DOT; para-DOT).<ref name="PiHKAL" /><ref name="Shulgin2003" />
In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') and other publications, Alexander Shulgin lists meta-DOT's dose as greater than 35{{nbsp}}mg orally and its duration 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 stimulation.<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 in rabbits, albeit with approximately 30-fold lower potency than DOM, though with somewhat greater potency than mescaline.<ref name="PiHKAL" /><ref name="JacobAndersonMeshul1977" />
The 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 (2-thio-TMA-2), 5-TOM (5-thio-DOM), and 5-TOET (5-thio-DOET), among others.<ref name="PiHKAL" /><ref name="Shulgin2003" />
Meta-DOT was first described in the 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 * DOx § Related compounds * 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