Structure via PubChem · Public domain (PubChem)
2-methylthio-4,5-dimethoxyamphetamine
Sign in to saveAlso known as ortho-DOT, 4,5-dimethoxy-2-methylthioamphetamine
Ortho-DOT, also known as 4,5-dimethoxy-2-methylthioamphetamine or as 2-thio-TMA-2, is a psychoactive drug of the phenethylamine and amphetamine families related to TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 2 position has been replaced with a methylthio group. In addition, the drug is a positional isomer of Aleph (DOT; para-DOT).
Chemical data
- Formula
- C12H19NO2S
- Molecular weight
- 241.35 g/mol
- IUPAC name
- 1-(4,5-dimethoxy-2-methylsulfanylphenyl)propan-2-amine
- SMILES
- CC(CC1=CC(=C(C=C1SC)OC)OC)N
- InChIKey
- GQUWSNDODZTHKC-UHFFFAOYSA-N
- XLogP
- 2.3
- Polar surface area
- 69.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 241.114
Show 2 more facts
- chemical formula
- C₁₂H₁₉NO₂S
- canonical SMILES
- CC(CC1=CC(=C(C=C1SC)OC)OC)N
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
Ortho-DOT, also known as 4,5-dimethoxy-2-methylthioamphetamine or as 2-thio-TMA-2, is a psychoactive drug of the phenethylamine and amphetamine families related to TMA-2. It is the analogue of TMA-2 in which the methoxy group at the 2 position has been replaced with a methylthio group. In addition, the drug is a positional isomer of Aleph (DOT; para-DOT).
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists ortho-DOT's dose as greater than 25mg orally and its duration as unknown. The effects of ortho-DOT have been reported to include threshold effects, vague awareness, a feeling of an impending something, and gastrointestinal disturbance. No clear hallucinogenic effects were described. Shulgin concluded that ortho-DOT was inactive. Higher doses were not tested.
Excerpted from Wikipedia’s “2-methylthio-4,5-dimethoxyamphetamine” article, available under the CC BY-SA 4.0 licence.