Synthesis, in vitro, and in vivo activity of N-p-substituted-benzyl- (- )- and (+)-N-normetazocines, (-)- and (+)-N-normorphinans, N- norketobemidones, and (-)-N-nor-4,5-epoxymorphinans

Everette L. May, Arthur E. Jacobson, Mariena V. Mattson, Andrew Coop, Mario D. Aceto, Edward R. Bowman, John R. Traynor, James H. Woods, Louis S. Harris

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

N-benzyl- and N-p-nitrobenzyl-N-norketobemidone, and N-p-fluorobenzyl- N-normetazocine have been synthesized and found to have equivalent or higher affinity for the (σ(i)-binding site than the previously described (+)-N- benzylnormetazocine. None of the examined compounds had significant affinity for the σ2-binding site and few had high affinity for μ-, δ-, and κ- opioid receptors. (-)-N-Benzyl-N-normetazocine displayed weak agonist- antagonist activity and (-)-N-benzylnoroxymorphone had one-tenth the antagonist activity of naloxone.

Original languageEnglish (US)
Pages (from-to)311-321
Number of pages11
JournalMedicinal Chemistry Research
Volume8
Issue number6
StatePublished - 1998
Externally publishedYes

ASJC Scopus subject areas

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

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