N-(Trifluoromethyl)benzyl substituted N-normetazocines and N-norketobemidones

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

Research output: Contribution to journalArticlepeer-review

1 Scopus citations


To further investigate the unusual profile of N-benzyl substituted opioids, N-trifluoromethylbenzyl normetazocines and norketobemidones were prepared. The introduction of trifluoromethyl substituents on the benzyl group of the (-)-metazocines reduced affinity at all three receptors, with the greatest loss at kappa receptors. Surprisingly, some of the (+)-normetazocines actually possessed higher affinity than the corresponding (-)-isomers. In the ketobemidone series, the effects were different - the 4-trifluoromethyl substituted ketobemidone actually possessed 3-fold higher mu affinity than the unsubstituted parent to give a ligand with good mu affinity. In functional in vitro assays, this compound was a weak antagonists, but in apparent contradiction it was inactive in in vivo assays.

Original languageEnglish (US)
Pages (from-to)31-33
Number of pages3
JournalBioorganic and Medicinal Chemistry
Issue number1
StatePublished - Jan 2 2003
Externally publishedYes

ASJC Scopus subject areas

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


Dive into the research topics of 'N-(Trifluoromethyl)benzyl substituted N-normetazocines and N-norketobemidones'. Together they form a unique fingerprint.

Cite this