An investigation of the N-demethylation of 3-deoxymorphine and the affinity of the alkylation products to μ, δ, and κ receptors

Csaba Csutoras, Ao Zhang, Jean M. Bidlack, John L. Neumeyer

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

The N-demethylation of 3-deoxymorphine (1) was investigated using methyl chloroformate and hydrazine. 3-Deoxynormorphine (2) was obtained in 70% yield, and 3-deoxydihydronormorphine (3) was also obtained as a side product. The μ, δ, and κ receptor binding affinity of a series of N-substituted 3-deoxynormorphines 6 and 7 and N-substituted 3-deoxydihydronormorphines 8-11 was also determined.

Original languageEnglish
Pages (from-to)2687-2690
Number of pages4
JournalBioorganic and Medicinal Chemistry
Volume12
Issue number10
DOIs
Publication statusPublished - May 15 2004

Keywords

  • Binding affinity
  • Codeine
  • Morphine
  • N-demethylation
  • Opioid receptor

ASJC Scopus subject areas

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

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