Synthetic studies of neoclerodane diterpenes from Salvia divinorum: role of the furan in affinity for opioid receptors.
Denise S Simpson, Kimberly M Lovell, Anthony Lozama, Nina Han, Victor W Day, Christina M Dersch, Richard B Rothman, Thomas E Prisinzano
Organic & biomolecular chemistry September 21, 2009 DOI: 10.1039/b905148a (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Experimental study Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Key findings | Piperidine 21 and thiomorpholine 23 are selective partial agonists at kappa opioid receptors. |
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.