3C-FP

3C-FP
Clinical data
Other names4-(3-Fluoropropoxy)-3,5-dimethoxyamphetamine; 3,5-Dimethoxy-4-(3-fluoropropoxy)amphetamine; α-Methylfluoroproscaline; 3C-Fluoroproscaline
Routes of
administration		Oral
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
Duration of action~8 hours
Identifiers
  • 1-[4-(3-fluoropropoxy)-3,5-dimethoxyphenyl]propan-2-amine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC14H22FNO3
Molar mass271.332 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=C(C(=C1)OC)OCCCF)OC)N
  • InChI=1S/C14H22FNO3/c1-10(16)7-11-8-12(17-2)14(13(9-11)18-3)19-6-4-5-15/h8-10H,4-7,16H2,1-3H3
  • Key:AKWFBZJFCPKTRW-UHFFFAOYSA-N

3C-FP, also known as 4-(3-fluoropropoxy)-3,5-dimethoxyamphetamine or as α-methylfluoroproscaline (3C-fluoroproscaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to TMA (3,4,5-TMA). It is the amphetamine (α-methyl) derivative of fluoroproscaline (FP).

According to Daniel Trachsel, 3C-FP's dose is 25 mg or more orally and its duration is approximately 8 hours. The specific effects of 3C-FP were not described.

The receptor interactions of 3C-FP have been studied. It shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 2,600–4,581 nM and 4,400 nM) and is a potent partial agonist of the serotonin 5-HT2A receptor (EC50Tooltip half-maximal effective concentration = 57 nM; EmaxTooltip maximal efficacy = 62%) but not of the serotonin 5-HT2B receptor (EC50 = >10,000 nM).

The chemical synthesis of 3C-FP has been described.

3C-FP was first described in the scientific literature by Trachsel in 2002. Subsequently, its pharmacology as well as its properties in humans were reported by Trachsel and colleagues in 2012, 2013, and 2021.

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. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  2. 1 2 3 Trachsel D (2002). "Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur-Aktivitätsbeziehungen, Mitteilung 1, Mescalin Derivate" [Synthesis of new (phenylalkyl)amines for the investigation of structure-activity relationships, Communication 1, Mescaline derivatives] (PDF). Helvetica Chimica Acta. 85 (9): 3019–3026. doi:10.1002/1522-2675(200209)85:9<3019::AID-HLCA3019>3.0.CO;2-4.
  3. 1 2 3 4 5 Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819. A series of 4-fluoroalkoxy analogs of 3,4,5-trimethoxyamphetamine (TMA, 12: 100–200 mg, 6–8 h[3]) has also been investigated (Figure 6, A).[86] The influence of fluorine introduction could not yet fully be determined, as at present too little biological data of either the non-fluorinated derivatives (85[3] and compounds described in Trachsel[86]) or the fluoro analogs 84 and 86–89 is available. For some fluorinated 3,4,5-substituted compounds some volunteers reported skin itching during experiments. Whether this might point towards the involvement of other targets, such as the histamine receptors, remains to be seen. [...] Some effects upon a-methyl introduction into the 3,4,5-series could also be observed. Among the very limited data so far, a slight increase of affinities for the a-methyl derivatives over their counterparts could be suggested at the 5-HT2A receptor (Table 2; s. pairs 72/84; 76/86; 77/87; 80/89).
  4. 1 2 3 4 5 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.