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Issue 18, 2009
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Synthetic studies of neoclerodane diterpenes from Salvia divinorum: role of the furan in affinity for opioid receptors

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Abstract

Further synthetic modification of the furan ring of salvinorin A (1), the major active component of Salvia divinorum, has resulted in novel neoclerodane diterpenes with opioid receptor affinity and activity. A computational study has predicted 1 to be a reproductive toxicant in mammals and is suggestive that use of 1 may be associated with adverse effects. We report in this study that piperidine 21 and thiomorpholine 23 have been identified as selective partial agonists at kappa opioid receptors. This indicates that additional structural modifications of 1 may provide ligands with good selectivity for opioid receptors but with reduced potential for toxicity.

Graphical abstract: Synthetic studies of neoclerodane diterpenes from Salvia divinorum: role of the furan in affinity for opioid receptors

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Publication details

The article was received on 13 Mar 2009, accepted on 08 Jun 2009 and first published on 14 Jul 2009


Article type: Paper
DOI: 10.1039/B905148A
Citation: Org. Biomol. Chem., 2009,7, 3748-3756
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    Synthetic studies of neoclerodane diterpenes from Salvia divinorum: role of the furan in affinity for opioid receptors

    D. S. Simpson, K. M. Lovell, A. Lozama, N. Han, V. W. Day, C. M. Dersch, R. B. Rothman and T. E. Prisinzano, Org. Biomol. Chem., 2009, 7, 3748
    DOI: 10.1039/B905148A

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