Fluorophen

Fluorophen
Clinical data
ATC code	None;
Identifiers
	IUPAC name (1R,9S,13R)-10-[2-(4-fluorophenyl)ethyl]-1,13-dimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-4-ol;
CAS Number	86495-14-9;
PubChemCID	3036297;
ChemSpider	2300351;
CompTox Dashboard(EPA)	DTXSID501006862;
Chemical and physical data
Formula	C22H26FNO
Molar mass	339.454 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Fc1ccc(cc1)CCN4[C@H]3Cc2c(cc(O)cc2)[C@@]([C@H]3C)(CC4)C;
	InChI InChI=1S/C22H26FNO/c1-15-21-13-17-5-8-19(25)14-20(17)22(15,2)10-12-24(21)11-9-16-3-6-18(23)7-4-16/h3-8,14-15,21,25H,9-13H2,1-2H3/t15-,21-,22+/m0/s1; Key:PUPFATUGTIQBQA-UZQPLGKSSA-N;

Fluorophen, or fluorofen, is a fluorinated analogue of phenazocine, an opioid drug of the benzomorphan group, which was developed as a radioligand for the purpose of labeling opioid receptors during PET scans (with ¹⁸F).^[1]^[2] Unlike most other benzomorphan derivatives, fluorophen acts as a full agonist of the opioid receptors with preferential affinity for the μ-opioid receptor (approximately 6x that of morphine), similar but slightly lower affinity for the δ-opioid receptor (equipotent to [D-Ala², D-Leu⁵]enkephalin), and very low affinity for the κ-opioid receptor.^[1]^[2]

References

1 2Rice KC, Konicki PE, Quirion R, Burke TR, Pert CB (November 1983). "Synthesis and pharmacological characterization of (±)-5,9 alpha-dimethyl-2-[2-(4-fluorophenyl)ethyl]-2'-hydroxy-6,7-benzomorphan (fluorophen), a ligand suitable for visualization of opiate receptors in vivo". Journal of Medicinal Chemistry. 26 (11): 1643–5. doi:10.1021/jm00365a017. PMID 6313921.
1 2Cody Paul Coyne (9 January 2008). Comparative Diagnostic Pharmacology: Clinical and Research Applications in Living-System Models. John Wiley & Sons. p. 692. ISBN 978-0-470-34429-3. Retrieved 22 April 2012.