TOMSO
title: "TOMSO" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["methoxyphenethylamines", "phenol-ethers", "pihkal", "psychedelic-phenethylamines", "substituted-amphetamines", "sulfoxides", "thio-2cs-and--dox"] topic_path: "general/methoxyphenethylamines" source: "https://en.wikipedia.org/wiki/TOMSO" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::data[format=table title="Infobox drug"]
| Field | Value |
|---|---|
| verifiedrevid | 470476429 |
| image | TOMSO.svg |
| image_class | skin-invert-image |
| width | 200px |
| routes_of_administration | Oral |
| class | Serotonergic psychedelic; Hallucinogen |
| ATC_prefix | None |
| duration_of_action | 10–16 hours |
| CAS_number_Ref | |
| CAS_number | 757142-16-8 |
| PubChem | 15915373 |
| ChemSpiderID_Ref | |
| ChemSpiderID | 21106387 |
| UNII_Ref | |
| UNII | 7SW3C48M3B |
| synonyms | 5-TOMSO; 5-TOM-sulfoxide; 2-Methoxy-4-methyl-5-methylsulfinylamphetamine |
| IUPAC_name | 1-[5-(methanesulfinyl)-2-methoxy-4-methylphenyl]propan-2-amine |
| C | 12 |
| SMILES | COC1=C(C=C(C(=C1)C)S(=O)C)CC(C)N |
| StdInChI_Ref | |
| StdInChI | 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 |
| StdInChIKey_Ref | |
| StdInChIKey | LMQLBXOYCGXTOM-UHFFFAOYSA-N |
| :: |
| verifiedrevid = 470476429 | drug_name = | image = TOMSO.svg | image_class = skin-invert-image | width = 200px | caption =
| pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral | class = Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
| legal_status =
| bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = 10–16 hours | excretion =
| CAS_number_Ref = | CAS_number = 757142-16-8 | CAS_supplemental = | PubChem = 15915373 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 21106387 | UNII_Ref = | UNII = 7SW3C48M3B | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = 5-TOMSO; 5-TOM-sulfoxide; 2-Methoxy-4-methyl-5-methylsulfinylamphetamine
| IUPAC_name = 1-[5-(methanesulfinyl)-2-methoxy-4-methylphenyl]propan-2-amine | C=12 | H=19 | N=1 | O=2 | S=1 | SMILES = COC1=C(C=C(C(=C1)C)S(=O)C)CC(C)N | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = LMQLBXOYCGXTOM-UHFFFAOYSA-N
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. It is the analogue of DOM in which the methoxy group at the 5 position has been replaced with a sulfur-containing methylsulfinyl group.
In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists TOMSO's dose as 150mg orally alone or 100 to 150mg orally in combination with alcohol and its duration as 10 to 16hours. 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. These effects included facial distortion and remarkable time dilation, among others. When combined with alcohol, "plus-two" and "plus-three" experiences occurred on the Shulgin Rating Scale.
The chemical synthesis of TOMSO has been described.
TOMSO was first described in the scientific literature by Alexander Shulgin and Peyton Jacob III in 1983. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.
References
References
- {{CitePiHKAL [http://www.erowid.org/library/books_online/pihkal/pihkal173.shtml TOMSO entry]
- (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.
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