5-TOM

Last updated
5-TOM
5-TOM.png
Clinical data
Other names2-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
  • 1-(2-methoxy-4-methyl-5-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=C1SC)CC(C)N)OC
  • 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

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]

Contents

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]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 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/pihkal172.shtml
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 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.
  3. 1 2 3 4 5 6 7 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.
  4. 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).
  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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