2-TOM

2-TOM, also known as 2-methylthio-4-methyl-5-methoxyamphetamine or as 2-thio-DOM, is a psychedelic drug of the phenethylamine and amphetamine families related to the DOx psychedelic DOM.^[1][2][3][4] It is the analogue of DOM in which the methoxy group at the 2 position has been replaced with a methylthio group.^[1][2][3][4] The drug is one of two possible TOM (thio-DOM) positional isomers, the other being 5-TOM.^[1][2][3][4]

Other names2-Methylthio-4-methyl-5-methoxyamphetamine; 5-Methoxy-4-methyl-2-methylthioamphetamine; 2-Thio-DOM; 2T-DOM; 2-Methylthio-DOM

Routes of
administrationOral^[1]

Drug classSerotonergic psychedelic; Hallucinogen

ATC code

• None

Quick facts Clinical data, Other names ...

2-TOM

Clinical data
Other names	2-Methylthio-4-methyl-5-methoxyamphetamine; 5-Methoxy-4-methyl-2-methylthioamphetamine; 2-Thio-DOM; 2T-DOM; 2-Methylthio-DOM
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	8–10 hours[1]
Identifiers
IUPAC name 1-(5-methoxy-4-methyl-2-methylsulfanylphenyl)propan-2-amine
CAS Number	207740-44-1
PubChem CID	15915345
ChemSpider	21106409
UNII	PWF2TYB2Z5
ChEMBL	ChEMBL123914
Chemical and physical data
Formula	C12H19NOS
Molar mass	225.35 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(=C(C=C1OC)CC(C)N)SC
InChI InChI=1S/C12H19NOS/c1-8-5-12(15-4)10(6-9(2)13)7-11(8)14-3/h5,7,9H,6,13H2,1-4H3 Key:CROYZNIEESCKGY-UHFFFAOYSA-N

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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 2-TOM's dose as 60 to 100 mg orally and its duration as 8 to 10 hours.^[1][2] Whereas 2-TOM has a fully effective dose of around 80 mg, DOM has a fully effective dose of about 5 mg, and so there is around a 15-fold loss of potency with the drug.^[1][2][3][5] In addition, it has a shorter duration than DOM, with DOM having a listed duration of 14 to 20 hours.^[1]

The effects of 2-TOM have been reported to include closed-eye visuals, feeling strange, "superb body feeling", pleasantness, bodily awareness, and feeling heavy.^[1] It has none of the neurological or physical "roughness" that was observed with 5-TOM.^[1]

The chemical synthesis of 2-TOM has been described.^[1][4] The phenethylamine analogue, 2C-2-TOM (2-thio-2C-D), has been synthesized, but was not tested and its properties are unknown.^[1][4] Bis-TOM, the 2,5-dimethylthio analogue of DOM, was synthesized and tested, but was inactive at doses of up to 160 mg orally or approximately 50 times the minimum effective dose of DOM.^[1][2][5][4]

2-TOM was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983.^[4] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.^[1]