2-TOM

Last updated
2-TOM
2-TOM.png
Clinical data
Other names2-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
  • 1-(5-methoxy-4-methyl-2-methylsulfanylphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C12H19NOS
Molar mass 225.35 g·mol−1
3D model (JSmol)
  • CC1=CC(=C(C=C1OC)CC(C)N)SC
  • 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

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]

Contents

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]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN   0-9630096-0-5. OCLC   25627628. https://www.erowid.org/library/books_online/pihkal/pihkal171.shtml
  2. 1 2 3 4 5 6 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN   978-0-12-433951-4. Archived from the original on 13 July 2025.
  3. 1 2 3 4 Nichols DE (1994). "Medicinal Chemistry and Structure-Activity Relationships". In Cho AK, Segal DS (eds.). Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. pp. 3–41. ISBN   978-0-12-173375-9. Biological activity is low in compounds in which the oxygen atom of either the 2- or the 5-methoxy group has been replaced with a sulfur, illustrating the difficulty in developing bioisosteres of the 2,5-dimethoxy-substituted aromatic nucleus. However, if relative importance were assigned to the two methoxy groups, the 2-methoxy group would appear to be more, critical for optimal activity (Jacob et al., 1977). For example, referring to Table l, when the 2-methoxy group of DOEt is replaced with a methylthio group, in vivo activity is reduced by more than one order of magnitude (Jacob and Shulgin, 1983; Shulgin and Shulgin, 1991). However, the replacement of the 5-methoxy oxygen with a sulfur reduces activity only 4- to 6-fold. Similarly, when the 2-methoxy group of DOM is replaced with a methylthio group, activity drops by a factor of 10–20, whereas similar replacement of the 5-methoxy only reduces activity 5- to 10-fold (Jacob et al., 1977; Shulgin and Shulgin, 1991).
  4. 1 2 3 4 5 6 7 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.
  5. 1 2 Marcher-Rørsted E, Halberstadt AL, Klein AK, Chatha M, Jademyr S, Jensen AA, Kristensen JL (May 2020). "Investigation of the 2,5-Dimethoxy Motif in Phenethylamine Serotonin 2A Receptor Agonists". ACS Chem Neurosci. 11 (9): 1238–1244. doi:10.1021/acschemneuro.0c00129. PMID   32212672. Shulgin observed that replacement of either the 2-position (10, Figure 2) or the 5- position (11, Figure 2) oxygen in 9 with a sulfur atom reduces its hallucinogenic potency by approximately 15- or 10-fold, respectively.13 Replacing both oxygen atoms with sulfur (12, Figure 2) completely abolished activity.
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