Alkylation of Opioid Receptor Subtypes by α-Chlornaltrexamine Produces Concurrent Irreversible Agonistic and Irreversible Antagonistic Activities1

L. M. Sayre, P. S. Portoghese, A. E. Takemori

Research output: Contribution to journalArticlepeer-review

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Abstract

α-Chlornaltrexamine (la, α-CNA), the C-6 epimer of the opioid receptor affinity label β-CNA (1b), has been synthesized and tested in vitro and in vivo. In vitro, α-CNA appears to alkylate opioid receptor subtypes μ κ, and δ) and is similar to β-CNA in its ability to produce irreversible antagonism at all three subtypes. However, la differs from lb in that it exhibits additionally an irreversible agonist activity in the guinea pig ileum preparation but not in the mouse vas deferens preparation. This latter activity is discussed in terms of an irreversible mixed agonism-antagonism at κ receptors, or, alternatively, it may reflect differences between μ receptors in the two in vitro preparations.

Original languageEnglish (US)
Pages (from-to)503-506
Number of pages4
JournalJournal of medicinal chemistry
Volume26
Issue number4
DOIs
StatePublished - Apr 1983

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