5-TOM

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

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

Routes of
administrationOral^[1]

Drug classSerotonergic psychedelic; Hallucinogen

ATC code

• None

Quick facts Clinical data, Other names ...

5-TOM

Clinical data
Other names	2-Methoxy-4-methyl-5-methylthioamphetamine; 5-Methylthio-4-methyl-2-methoxyamphetamine; 5-Thio-DOM; 5T-DOM; 5-Methylthio-DOM
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Onset of action	30 minutes[2][1] Peak: ~3 hours[2][1]
Duration of action	6–10 hours (but up to 12–16 hours)[1][2]
Identifiers
IUPAC name 1-(2-methoxy-4-methyl-5-methylsulfanylphenyl)propan-2-amine
CAS Number	207740-45-2
PubChem CID	15915349
ChemSpider	21106388
UNII	C4U5T6C5LG
ChEMBL	ChEMBL338149
Chemical and physical data
Formula	C12H19NOS
Molar mass	225.35 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(=C(C=C1SC)CC(C)N)OC
InChI InChI=1S/C12H19NOS/c1-8-5-11(14-3)10(6-9(2)13)7-12(8)15-4/h5,7,9H,6,13H2,1-4H3 Key:DPPFTYBYPWHNRM-UHFFFAOYSA-N

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In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 5-TOM's dose as 30 to 50 mg orally and its duration as 6 to 10 hours (but up to 12–16 hours).^[1][3][2] Its onset is about 30 minutes and its time to peak is a little over 3 hours.^[2] Whereas 5-TOM has an effective dose of around 40 mg, DOM has a fully effective dose of about 5 mg, and so there is around an 8-fold loss of potency with the drug.^[1][3][4][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 5-TOM have been reported to include sensory enhancement, closed-eye imagery and fantasy, substantial open-eye visuals and some visual distortions, catatonia-like state, "pretty heavy-duty experience", body load, generalized discomfort or malaise, neurological discoordination, gastrointestinal disturbance such as cramping and nausea, irritability, anger, sleep disturbance, and next-day lethargy.^[1][2] According to Shulgin, there were no completely positive experiences, more negative reports than positive ones, not even many neutral reports, and the consensus being that the drug wasn't worth the struggle.^[1] There also appears to be significant interindividual variability in intensity of 5-TOM.^[1][2]

The chemical synthesis of 5-TOM has been described.^[1][2] The phenethylamine analogue, 2C-5-TOM (5-thio-2C-D), has been synthesized, but was not tested and its properties are unknown.^[1][2] 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][3][5][2] TOMSO is the sulfoxide of 5-TOM, and produced few effects on its own at doses of up to 150 mg orally.^[1][3][2]

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