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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

Year: 1983

Type: article

Abstract: A fluorinated derivative of the benzomorphan opiate agonist phenazocine, (+/-)-5,9 alpha-dimethyl-2-[2-(4-fluorophenyl)ethyl]-2'-hydroxy-6, 7-benzomorphan (fluorophen), was prepared by N-acylation of (+/-)-5,9 alpha-dimethyl-2'-hydroxybenzomorphan with (p-fluorophenyl)acetyl chloride, followed by diborane reduction of the resulting amide. Fluorination produces only a twofold opiate receptor affinity loss when measured either by bioassay or receptor binding (selectivity mu congruent to delta greater than kappa). Labeled with 18F, fluorophen should be sufficiently potent to be useful as an in vivo probe for visualizing opiate receptors by positron emission transaxial tomography (PETT).

Source: Journal of Medicinal Chemistry

DOI: 10.1021/jm00365a017

Authors: Kenner C. Rice, P. Eric Konicki, Remi Quirion, Terrence R. Burke, Candace B. Pert

Language: English

Topic: Neuropeptides and Animal Physiology

Subfield: Cellular and Molecular Neuroscience

Field: Neuroscience

Domain: Life Sciences

SDG: Good health and well-being

Open Access status: green

OpenAlex ID: W2087977018

FWCI: 0.552

Cites:

Cited by: 4

Related to: 10