Trifluoromescaline

Mescaline derivative From Wikipedia, the free encyclopedia

Trifluoromescaline (TFM), also known as 4-(trifluoromethoxy)-3,5-dimethoxyphenethylamine, is a derivative of the phenethylamine psychedelic mescaline, which has a 4-trifluoromethoxy group replacing the 4-methoxy group of mescaline.[2][1][3]

Other namesTFM; 4-(Trifluoromethoxy)-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-(trifluoromethoxy)phenethylamine
ATC code
  • None
Quick facts Clinical data, Other names ...
Trifluoromescaline
Clinical data
Other namesTFM; 4-(Trifluoromethoxy)-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-(trifluoromethoxy)phenethylamine
Routes of
administration
Oral[1][2]
Drug classSerotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action14–24 hours[1][2]
Identifiers
  • 2-[3,5-dimethoxy-4-(trifluoromethoxy)phenyl]ethanamine
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H14F3NO3
Molar mass265.232 g·mol−1
3D model (JSmol)
  • COc1cc(CCN)cc(OC)c1OC(F)(F)F
  • InChI=1S/C11H14F3NO3/c1-16-8-5-7(3-4-15)6-9(17-2)10(8)18-11(12,13)14/h5-6H,3-4,15H2,1-2H3
  • Key:AVPVNYDXWCNFJD-UHFFFAOYSA-N
Close

It was found to be one of the most potent compounds in the scaline series, with a reported dose of 15 to 40 mg (and 60 mg being described as a "strong overdose"), and a slow onset of action and long duration of effects, lasting 14 to 24 hours.[2]

The drug showed about 34-fold higher affinity and 36-fold greater activational potency at the serotonin 5-HT2A receptor compared to mescaline in vitro.[3] In addition, it appears to be much more lipophilic than mescaline (predicted log P = 1.9 vs. 0.7, respectively).[4][5]

Analogues of trifluoromescaline include the fluorinated scalines difluoromescaline, metadifluoromescaline, fluoroescaline, difluoroescaline, trifluoroescaline, fluoroproscaline, and trifluoroproscaline, among others. Some other analogues include the fluorinated phenethylamines 2C-TFM, DOTFM, 2C-TFE, DOTFE, 2C-T-28 (2C-T-FP), 2C-T-36 (2C-T-TFM), and 3C-DFE, among others.

TFM was first described in the scientific literature by Daniel Trachsel by 2012.[1][2] Many other related compounds have also been described by Trachsel and colleagues.[6][1][2] It is not a controlled substance in Canada as of 2025.[7]

See also

References

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