2,5-Dimethoxy-4-trifluoromethylamphetamine

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DOTFM
2,5-Dimethoxy-4-trifluoromethylamphetamine.svg
Clinical data
Other names2,5-Dimethoxy-4-trifluoromethylamphetamine; DOTFM
Legal status
Legal status
Identifiers
  • (RS)-1-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H16F3NO2
Molar mass 263.260 g·mol−1
3D model (JSmol)
  • FC(F)(F)c1cc(OC)c(cc1OC)CC(N)C
  • InChI=1S/C12H16F3NO2/c1-7(16)4-8-5-11(18-3)9(12(13,14)15)6-10(8)17-2/h5-7H,4,16H2,1-3H3 Yes check.svgY
  • Key:WPGOTSORDNBMHP-UHFFFAOYSA-N Yes check.svgY
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2,5-Dimethoxy-4-trifluoromethylamphetamine (DOTFM) is a psychedelic drug of the substituted phenethylamine, substituted amphetamine, and DOx (where 'x' indicates a 4-substitution on the phenyl group of 2,5-dimethoxyamphetamine) classes. It was first synthesized in 1994 by a team at Purdue University led by David E. Nichols. [1] DOTFM is the α-methylated analogue of 2C-TFM and would be named 3C-TFM using this specific acronymic code.

It acts as an agonist at the serotonin 5-HT2A and 5-HT2C receptors. [1] In drug discrimination tests in rats, DOTFM fully substituted for LSD and was slightly more potent than DOI. [1] In addition, (R)-DOTFM robustly induces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, with equivalent potency as (R)-DOI. [2] The drug is around twice as potent as 2C-TFM in animal studies.

In contrast to (R)-DOI, which has extraordinarily potent serotonin 5-HT2A receptor-mediated anti-inflammatory effects, [3] [4] DOTFM shows no anti-inflammatory effects. [5] The differences between the drugs in this regard appear to be due to differences in functional selectivity at the serotonin 5-HT2A receptor. [5] [2]

See also

References

  1. 1 2 3 Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Gudelsky GA, et al. (December 1994). "1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist". Journal of Medicinal Chemistry. 37 (25): 4346–4351. doi:10.1021/jm00051a011. PMID   7996545.
  2. 1 2 Flanagan TW, Foster TP, Galbato TE, Lum PY, Louie B, Song G, et al. (February 2024). "Serotonin-2 Receptor Agonists Produce Anti-inflammatory Effects through Functionally Selective Mechanisms That Involve the Suppression of Disease-Induced Arginase 1 Expression". ACS Pharmacology & Translational Science. 7 (2): 478–492. doi:10.1021/acsptsci.3c00297. PMC   10863441 . PMID   38357283. The effects of (R)-DOTFM were examined in the head-twitch response (HTR) assay. (R)-DOTFM produced a strong HTR with a potent ED 50 of 0.60 μmol/kg. These values are equivalent to (R)-DOI, as previously determined.{{cite journal}}: CS1 maint: overridden setting (link)
  3. ↑ Nichols DE, Johnson MW, Nichols CD (February 2017). "Psychedelics as Medicines: An Emerging New Paradigm". Clinical Pharmacology and Therapeutics. 101 (2): 209–219. doi:10.1002/cpt.557. PMID   28019026.
  4. ↑ Yu B, Becnel J, Zerfaoui M, Rohatgi R, Boulares AH, Nichols CD (November 2008). "Serotonin 5-hydroxytryptamine(2A) receptor activation suppresses tumor necrosis factor-alpha-induced inflammation with extraordinary potency". The Journal of Pharmacology and Experimental Therapeutics. 327 (2): 316–323. doi:10.1124/jpet.108.143461. PMID   18708586.
  5. 1 2 Flanagan TW, Billac G, Nichols CD (2022). "Differential Regulation of Inflammatory Responses Following 5-HT 2 Receptor Activation in Pulmonary Tissues". The FASEB Journal. 36 (S1). doi: 10.1096/fasebj.2022.36.S1.R2617 . ISSN   0892-6638.
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