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.

doi:10.1021/JM00365A017

Paper

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.

Published Nov 1, 1983 · K. Rice, P. Konicki, R. Quirion

Journal of medicinal chemistry

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5

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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).

In Vitro Study

Study Snapshot

Fluorophen, a fluorinated derivative of phenazocine, shows potential as an in vivo probe for visualizing opiate receptors using positron emission tomography.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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.

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