 | |
| Clinical data | |
|---|---|
| Other names | 4-(3-Fluoropropoxy)-3,5-dimethoxyamphetamine; 3,5-Dimethoxy-4-(3-fluoropropoxy)amphetamine; α-Methylfluoroproscaline; 3C-Fluoroproscaline |
| Routes of administration | Oral[1] |
| Drug class | Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen |
| ATC code |
|
| Pharmacokinetic data | |
| Duration of action | ~8 hours[1] |
| Identifiers | |
| |
| PubChem CID | |
| ChemSpider | |
| Chemical and physical data | |
| Formula | C14H22FNO3 |
| Molar mass | 271.332 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
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).[1][2][3][4] It is the amphetamine (α-methyl) derivative of fluoroproscaline (FP).[1][3][4]
According to Daniel Trachsel, 3C-FP's dose is 25 mg or more orally and its duration is approximately 8 hours.[1] The specific effects of 3C-FP were not described.[1]
The receptor interactions of 3C-FP have been studied.[4][3] 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).[4][3]
The chemical synthesis of 3C-FP has been described.[2]
3C-FP was first described in the scientific literature by Trachsel in 2002.[2] Subsequently, its pharmacology as well as its properties in humans were reported by Trachsel and colleagues in 2012,[3] 2013,[1] and 2021.[4]
See also
References
- 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.
- 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.
- 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).
- 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.