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Fluorophen

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Chemical compound

Pharmaceutical compound

Fluorophen
Clinical data

ATC code	None
Identifiers
IUPAC name (1R,9S,13R)-10-[2-(4-fluorophenyl)ethyl]-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,7]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, orfluorofen, is a fluorinatedanalogue ofphenazocine, anopioid drug of thebenzomorphan group, which was developed as aradioligand for the purpose of labelingopioid receptors duringPET scans (with¹⁸F).^[1]^[2] Unlike most other benzomorphan derivatives, fluorophen acts as afull agonist of the opioid receptors with preferentialaffinity for theμ-opioid receptor (approximately 6x that of morphine), similar but slightly lower affinity for theδ-opioid receptor (equipotent to[D-Ala²,D-Leu⁵]enkephalin), and very low affinity for theκ-opioid receptor.^[1]^[2]

^^a ^bRice 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.
^^a ^bCody 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. Retrieved22 April 2012.