Synthetic studies of neoclerodane diterpenes from Salvia divinorum: exploration of the 1-position.
Kenneth G Holden, Kevin Tidgewell, Alfred Marquam, Richard B Rothman, Hernan Navarro, Thomas E Prisinzano
Bioorganic & Medicinal Chemistry Letters November 15, 2007 DOI: 10.1016/j.bmcl.2007.09.050 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Key points | The C-1 ketone of herkinorin is essential for mu agonist activity; removing it converts the compound to a weak antagonist. |
Abstract
Modification of the C-1 ketone of salvinorin A (2a) produces analogues with opioid antagonist properties. Of particular significance is the finding that 1-deoxo-1,10-dehydrosalvinorin A (11a) is a moderately potent antagonist at all three opioid receptor subtypes, and that herkinorin (2b), a mu agonist, is converted to a weak antagonist by removal of the C-1 ketone (3b and 11b). These observations suggest that the ketone of 2b is a key structural feature responsible for mu agonist activity.
Citations in the library
Cited by 14
- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. Pharmacological Reviews June 1, 2011
- Legally high? Legal considerations of Salvia divinorum. Journal of Psychoactive Drugs June 1, 2008
- Semisynthetic neoclerodanes as kappa opioid receptor probes. Bioorganic & Medicinal Chemistry May 1, 2012
- Selective natural kappa opioid and cannabinoid receptor agonists with a potential role in the treatment of gastrointestinal dysfunction Drug News & Perspectives 2009
- Synthesis of neoclerodane diterpenes and their pharmacological effects. Topics in current chemistry 2011
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Cites 13
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- Salvinorin A: allosteric interactions at the mu-opioid receptor. Journal of Pharmacology and Experimental Therapeutics February 1, 2007
- A facile method for the preparation of deuterium labeled salvinorin A: synthesis of [2,2,2-2H3]-salvinorin A. Bioorganic & Medicinal Chemistry Letters October 18, 2004
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