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Bioorg Med Chem Lett. 2007 Nov 15;17(22):6111-5. Epub 2007 Sep 15.

Synthetic studies of neoclerodane diterpenes from Salvia divinorum: exploration of the 1-position.

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  • 1Holden Laboratories, Carmel, CA 93923, USA.


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.

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