TOMSO

TOMSO, or 5-TOMSO, also known as 2-methoxy-4-methyl-5-methylsulfinylamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families related to the DOx series.^[1][2] It is the analogue of DOM in which the methoxy group at the 5 position has been replaced with a sulfur-containing methylsulfinyl group.^[1][2] In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists TOMSO's dose as >150 mg orally alone or 100 to 150 mg orally in combination with alcohol and its duration as 10 to 16 hours.^[1] TOMSO was reported to produce no or only threshold effects by itself at the assessed doses, but when alcohol was concomitantly ingested, clear hallucinogenic effects occurred.^[1] These effects included facial distortion and remarkable time dilation, among others.^[1] When combined with alcohol, "plus-two" and "plus-three" experiences occurred on the Shulgin Rating Scale.^[1] TOMSO 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]

TOMSO

Clinical data
Other names	2-Methoxy-4-methyl-5-methylsulfinylamphetamine
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Pharmacokinetic data
Duration of action	10–16 hours[1]
Identifiers
IUPAC name 1-[5-(methanesulfinyl)-2-methoxy-4-methylphenyl]propan-2-amine
CAS Number	757142-16-8 Y
PubChem CID	15915373
ChemSpider	21106387 Y
UNII	7SW3C48M3B
CompTox Dashboard (EPA)	DTXSID901027145
Chemical and physical data
Formula	C12H19NO2S
Molar mass	241.35 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=C(C=C(C(=C1)C)S(=O)C)CC(C)N
InChI InChI=1S/C12H19NO2S/c1-8-5-11(15-3)10(6-9(2)13)7-12(8)16(4)14/h5,7,9H,6,13H2,1-4H3 Y Key:LMQLBXOYCGXTOM-UHFFFAOYSA-N Y
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See also

• Substituted methoxyphenethylamine
• TOM (psychedelic)