Trifluoromescaline

Last updated
Trifluoromescaline
Trifluoromescaline.svg
Clinical data
Other namesTFM; 4-(Trifluoromethoxy)-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-(trifluoromethoxy)phenethylamine
Routes of
administration 		Oral [1] [2]
Drug class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 2-[3,5-dimethoxy-4-(trifluoromethoxy)phenyl]ethanamine
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H14F3NO3
Molar mass 265.232 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

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. 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 or more. [2] The drug showed about 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] 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]

Contents

See also

References

  1. 1 2 3 Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Test Anal. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID   22374819.
  2. 1 2 3 4 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine Von der Struktur zur Funktion. Nachtschatten Verlag AG. pp. 704–723. ISBN   978-3-03788-700-4.
  3. ↑ Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021). "Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines". Front Pharmacol. 12 794254. doi: 10.3389/fphar.2021.794254 . PMC   8865417 . PMID   35222010.
  4. ↑ "Trifluoromescaline". PubChem. Retrieved 19 July 2025.
  5. ↑ "Mescaline". PubChem. Retrieved 19 July 2025.
  6. ↑ Trachsel D (2002). "Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, Mescalin Derivate". Helvetica Chimica Acta. 85 (9): 3019–3026. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4.
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