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The Orvinols and Related Opioids - High Affinity Ligands with Diverse Efficacy Profiles

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The thevinols and orvinols derived from thebaine via the thebaine-methylvinyl ketone adduct (thevinone) were thoroughly investigated in the 1960's and 1970's by the Reckitt group. From this work a number of important opioids emerged. Buprenorphine is a m partial agonist, κ / δ-antagonist that is now used primarily in the treatment of heroin abuse and dependence though it was initially launched as an analgesic for the treatment of moderate to severe pain. Etorphine and dihydroetorphine are very potent m agonists that have found application in vetinary and human medicine respectively. Diprenorphine is primarily a m antagonist though it also has some κ-partial agonist effects. It has high affinity for all types of opioid receptors and as a 'universal' opioid ligand has been much in demand as a pharmacological tool. It has also been converted into a [ 11 C] version for use in Positron Emission Tomography (PET) studies of brain function related to the opioid receptor system.

More recent medicinal chemistry investigations have been concerned with gaining a greater understanding of buprenorphine's unique opioid profile. This has involved the synthesis and evaluation of a number of series of buprenorphine analogues in which the C20 t-butyl group has been constrained in a ring system. These studies have suggested that the methyls in the t-butyl group inhibit the conformational changes in the k-receptor required for generation of an agonist response. Introduction of a 7α-cinnamoylaminomethyl group in place of the orvinol tertiary alcohol function leads to selective irreversible μ antagonism.
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Keywords: antagonism; cinnamoylaminomethyl; orvinol tertiary alcohol; receptor

Document Type: Review Article

Affiliations: Department of Pharmacy and Pharmacology University of Bath Claverton Down Bath BA2 7AY UK.

Publication date: 01 March 2004

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  • Current Pharmaceutical Design publishes timely in-depth reviews covering all aspects of current research in rational drug design. Each issue is devoted to a single major therapeutic area. A Guest Editor who is an acknowledged authority in a therapeutic field has solicits for each issue comprehensive and timely reviews from leading researchers in the pharmaceutical industry and academia.

    Each thematic issue of Current Pharmaceutical Design covers all subject areas of major importance to modern drug design, including: medicinal chemistry, pharmacology, drug targets and disease mechanism.
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