The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans

Matthew D. Metcalf, Mario D. Aceto, Louis S. Harris, James H. Woods, John R. Traynor, Andrew Coop, Everette L. May

Research output: Contribution to journalArticle

5 Scopus citations

Abstract

To investigate the effects of carboxylic ester and acid moieties as the N-substituent of opioids, a short series of racemic N-substituted normetazocines was prepared. The introduction of both groups as the normetazocine N-substituent produced compounds which displayed low potency in vitro and in vivo, with the esters displaying the greater activity. The pharmacology of the compounds is discussed with implications resulting from potential in vivo metabolic hydrolysis.

Original languageEnglish (US)
Pages (from-to)869-873
Number of pages5
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number2
DOIs
StatePublished - Jan 15 2008
Externally publishedYes

Keywords

  • Benzomorphan
  • N-Normetazocine
  • Normetazocine
  • Opioid

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'The influence of esters and carboxylic acids as the N-substituent of opioids. Part 1: Benzomorphans'. Together they form a unique fingerprint.

Cite this