Trifluoroproscaline

Trifluoroproscaline
Clinical data
Other names	TFP; 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
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code	None;
Pharmacokinetic data
Duration of action	Unknown
Identifiers
	IUPAC name 2-[3,5-dimethoxy-4-(3,3,3-trifluoropropoxy)phenyl]ethanamine;
PubChem CID	64565107;
ChemSpider	46326946;
Chemical and physical data
Formula	C13H18F3NO3
Molar mass	293.286 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(=CC(=C1OCCC(F)(F)F)OC)CCN;
	InChI 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-HT_2A 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]

References

^ ^a ^b ^c ^d ^e ^f ^g 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.
^ ^a ^b ^c ^d ^e ^f 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.
^ ^a ^b ^c ^d ^e ^f ^g ^h 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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