Trifluoroproscaline

Last updated

Trifluoroproscaline
Trifluoroproscaline.svg
Clinical data
Other namesTFP; 3,3,3-Trifluoroproscaline; 3,3,3-TFP; 4-(3,3,3-Trifluoropropoxy)-3,5-dimethoxyphenethylamine; 3,5-Dimethoxy-4-(3,3,3-trifluoropropoxy)phenethylamine
Routes of
administration 		Oral [1] [2] [3]
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action Unknown [1] [3]
Identifiers
  • 2-[3,5-dimethoxy-4-(3,3,3-trifluoropropoxy)phenyl]ethanamine
PubChem CID
ChemSpider
Chemical and physical data
Formula C13H18F3NO3
Molar mass 293.286 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1OCCC(F)(F)F)OC)CCN
  • InChI=1S/C13H18F3NO3/c1-18-10-7-9(3-5-17)8-11(19-2)12(10)20-6-4-13(14,15)16/h7-8H,3-6,17H2,1-2H3
  • Key:SANRTCNYSAUXOQ-UHFFFAOYSA-N

Trifluoroproscaline (TFP), also known as 4-(3,3,3-trifluoropropoxy)-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. [1] [2] [3] It is a trifluorinated derivative of proscaline. [1] [2] [3] Based on limited trials, trifluoroproscaline is active at a dose of 33 to 66 mg or more orally and its duration is unknown. [1] [2] [3] Initial trials provided evidence of effects including good fantasy and slight color intensification. [1] The drug might be less potent than proscaline similarly to fluoroproscaline. [2] It acts as a low-potency serotonin 5-HT2A receptor partial agonist and also interacts with other serotonin receptors and targets. [3] Trifluoroproscaline was first described in the scientific literature by Daniel Trachsel in 2012. [1] [3] [2] Its pharmacology was subsequently studied in greater detail in 2021. [3]

Contents

See also

References

  1. 1 2 3 4 5 6 7 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 706, 712. ISBN   978-3-03788-700-4. OCLC   858805226.
  2. 1 2 3 4 5 6 Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID   22374819. A fluorinated analog of proscaline (79) [3] was also investigated.[86] At the cloned [3 H]ketanserin-labelled serotonin h5-HT2A receptor fluoroproscaline (80: Ki= 8792nM) showed only low affinity and in humans, fluoroproscaline (80: 60–150 mg, 3–5 h) was distinctly less potent and of shorter duration than proscaline (79: 30–60 mg, 8–12 h). Similarly, limited trials suggest that trifluoroproscaline (81: 66 mg or more) might be less potent as well.
  3. 1 2 3 4 5 6 7 8 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". Frontiers in Pharmacology. 12 794254. doi: 10.3389/fphar.2021.794254 . PMC   8865417 . PMID   35222010.
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