Meta-DOT

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.^[1][2] It is the analogue of TMA-2 in which the methoxy group at the 5 position has been replaced with a methylthio group.^[1][2] In addition, the drug is a positional isomer of Aleph (DOT; para-DOT).^[1][2]

Other names5-Methylthio-2,4-dimethoxyamphetamine; 2,4-Dimethoxy-5-methylthioamphetamine; 5-Thio-TMA-2

Routes of
administrationOral^[1]

Drug classPsychoactive drug

ATC code

• None

Quick facts Clinical data, Other names ...

Meta-DOT

Clinical data
Other names	5-Methylthio-2,4-dimethoxyamphetamine; 2,4-Dimethoxy-5-methylthioamphetamine; 5-Thio-TMA-2
Routes of administration	Oral[1]
Drug class	Psychoactive drug
ATC code	None
Pharmacokinetic data
Duration of action	Unknown[1]
Identifiers
IUPAC name 1-[2,4-dimethoxy-5-(methylsulfanyl)phenyl]propan-2-amine
CAS Number	79440-52-1 Y
PubChem CID	144891
ChemSpider	127832 Y
UNII	8A89CW1FXK
ChEMBL	ChEMBL31787 Y
CompTox Dashboard (EPA)	DTXSID701000472
Chemical and physical data
Formula	C12H19NO2S
Molar mass	241.35 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1cc(OC)c(cc1SC)CC(N)C)C
InChI InChI=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 Y Key:BEMIKIUJWHLJTP-UHFFFAOYSA-N Y
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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists meta-DOT's dose as greater than 35 mg orally and its duration as unknown.^[1][2] 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.^[1] However, the effects at tested doses were not said to be completely believable and Shulgin concluded that it was inactive.^[1][2] Higher doses were not tested.^[1]

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.^[1][3]

The chemical synthesis of meta-DOT has been described.^[1][3] 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.^[1][2]

Meta-DOT was first described in the scientific literature by Shulgin and colleagues in 1977.^[3] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.^[1]