2-TOM

2-TOM
Clinical data
Other names	2-Methylthio-4-methyl-5-methoxyamphetamine; 5-Methoxy-4-methyl-2-methylthioamphetamine; 2-Thio-DOM; 2T-DOM; 2-Methylthio-DOM
Routes of; administration	Oral
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None;
Pharmacokinetic data
Duration of action	8–10 hours
Identifiers
	IUPAC name 1-(5-methoxy-4-methyl-2-methylsulfanylphenyl)propan-2-amine;
CAS Number	207740-44-1;
PubChem CID	15915345;
ChemSpider	21106409;
UNII	PWF2TYB2Z5;
ChEMBL	ChEMBL123914;
Chemical and physical data
Formula	C12H19NOS
Molar mass	225.35 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC(=C(C=C1OC)CC(C)N)SC;
	InChI 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]

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]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ 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
^ ^a ^b ^c ^d ^e ^f 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.
^ ^a ^b ^c ^d 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).
^ ^a ^b ^c ^d ^e ^f ^g 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.
^ ^a ^b 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.

External links

[PiHKAL-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ 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

[Shulgin2003-2] ^ ^a ^b ^c ^d ^e ^f 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.

[Nichols1994-3] 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).

[JacobShulgin1983-4] ^ ^a ^b ^c ^d ^e ^f ^g 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.

[Marcher-RørstedHalberstadtKlein2020-5] 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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See also

References

External links