Synthesis and Evaluation of 1- and 2-Substituted Fentanyl Analogues for Opioid Activity

Mohamed Y.H. Essawi, Philip S. Portoghese

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

We synthesized fentanyl analogues that possess key groups common to the opioid peptides to investigate whether or not these two classes of compounds interact with common subsites on opioid receptors. The design of the analogues was based on the possibility of structural analogy between the two aromatic rings of fentanyl and the Tyr1 and Phe4 residues of the opioid peptides. The synthesized compounds showed very weak or no opioid activity as tested in the electrically stimulated longitudinal muscle of the guinea pig ileum or mouse vas deferens preparations. These results, together with those of reported studies, suggest that fentanyl and the opioid peptides interact with different subsites on either μ or δ receptors. Studies using the irreversible μ opioid receptor antagonist, β-funaltrexamine, indicate that fentanyl interacts preferentially with μ opioid receptors.

Original languageEnglish (US)
Pages (from-to)348-352
Number of pages5
JournalJournal of medicinal chemistry
Volume26
Issue number3
DOIs
StatePublished - Mar 1983

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