| Verifiedrevid | 415883653 |
|---|---|
| Width | 225px |
| Routes of administration | Oral[1] |
| Class | Psychoactive drug |
| Atc prefix | None |
| Duration of action | Unknown[1] |
| Cas number | 79440-51-0 |
| Pubchem | 144890 |
| Chemspiderid | 127831 |
| Unii | FQL7H4OV45 |
| Chembl | 31077 |
| Synonyms | o-DOT; 4,5-Dimethoxy-2-methylthioamphetamine; 2-Methylthio-4,5-dimethoxyamphetamine; 2-Thio-TMA-2 |
| Iupac name | 1-[4,5-dimethoxy-2-(methylsulfanyl)phenyl]propan-2-amine |
| C | 12 |
| H | 19 |
| N | 1 |
| O | 2 |
| S | 1 |
| Smiles | S(c1cc(OC)c(OC)cc1CC(N)C)C |
| Stdinchi | 1S/C12H19NO2S/c1-8(13)5-9-6-10(14-2)11(15-3)7-12(9)16-4/h6-8H,5,13H2,1-4H3 |
| Stdinchikey | GQUWSNDODZTHKC-UHFFFAOYSA-N |
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.[1][2] It is the analogue of TMA-2 in which the methoxy group at the 2 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]
In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists ortho-DOT's dose as greater than 25 mg orally and its duration as unknown.[1][2] The effects of ortho-DOT have been reported to include threshold effects, vague awareness, a feeling of an impending something, and gastrointestinal disturbance.[1] No clear hallucinogenic effects were described.[1] Shulgin concluded that ortho-DOT was inactive.[2] Higher doses were not tested.[1]
Ortho-DOT has been found to produce hyperthermia in rabbits, albeit with approximately 50-fold lower potency than DOM, though with somewhat greater potency than mescaline.[1][3][4]
The chemical synthesis of ortho-DOT has been described.[1][3] Analogues of ortho-DOT include TMA-2, Aleph (DOT; para-DOT; 4-thio-TMA-2), meta-DOT (5-thio-TMA-2), 2-TOM (2-thio-DOM), and 2-TOET (2-thio-DOET), among others.[1][2]
Ortho-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]
See also
References
- ^ Ortho-DOT entry
- ^ Shulgin AT (2003). "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived 13 July 2025 at the Wayback Machine.
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.
- ^ Jacob P, Anderson G, Meshul CK, Shulgin AT, Castagnoli N (October 1977). "Monomethylthio analogues of 1-(2,4,5-trimethoxyphenyl)-2-aminopropane". J Med Chem. 20 (10): 1235–1239. doi:10.1021/jm00220a001. PMID 903913. Archived 2025-07-12 at the Wayback Machine.
- ^ Anderson GM, Castagnoli N, Kollman PA (1978). "Quantitative structure-activity relationships in the 2,4,5-ring substituted phenylisopropylamines". NIDA Res Monogr. ' (22): 199–217. PMID 101881