TOMSO

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TOMSO
Clinical data
Other names5-TOMSO; 5-TOM-sulfoxide; 2-Methoxy-4-methyl-5-methylsulfinylamphetamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action10–16 hours[1]
Identifiers
  • 1-[5-(methanesulfinyl)-2-methoxy-4-methylphenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H19NO2S
Molar mass241.35 g·mol−1
3D model (JSmol)
  • COC1=C(C=C(C(=C1)C)S(=O)C)CC(C)N
  • 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 checkY
  • Key:LMQLBXOYCGXTOM-UHFFFAOYSA-N checkY
  (verify)

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]

The chemical synthesis of TOMSO has been described.[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]

See also

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References

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  1. ^ a b c d e f g h i j Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. TOMSO entry
  2. ^ a b c Jacob P, Shulgin AT (May 1983). "Sulfur analogues of psychotomimetic agents. 2. Analogues of (2,5-dimethoxy-4-methylphenyl)-and (2,5-dimethoxy-4-ethylphenyl)isopropylamine". J Med Chem. 26 (5): 746–752. doi:10.1021/jm00359a021. PMID 6842515.
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