Synthesis of salvinorin A analogues as opioid receptor probes.
Kevin Tidgewell, Wayne W Harding, Anthony Lozama, Howard Cobb, Kushal Shah, Pavitra Kannan, Christina M Dersch, Damon Parrish, Jeffrey R Deschamps, Richard B Rothman, Thomas E Prisinzano
Journal of Natural Products June 2006 DOI: 10.1021/np060094b (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Key points | Reports the semisynthesis of neoclerodane diterpene analogues from salvinorin A and their structure-affinity relationships at opioid receptors, with the aim of enabling further development of novel opioid receptor ligands. No specific affinity values are stated in the abstract. |
Abstract
Several neoclerodanes, such as salvinorin A (1) and herkinorin (3), have recently been shown to possess opioid receptor activity in vitro and in vivo. To explore the structure-affinity relationships of this interesting class of compounds, we have synthesized a series of analogues from 1 isolated from Salvia divinorum. Here, we report the semisynthesis of neoclerodane diterpenes and their structure-affinity relationships at opioid receptors. This work will allow the further development of novel opioid receptor ligands.
Comparable studies
Other theoretical and historical papers on salvia divinorum, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A. | 2008 | Theoretical or philosophical paper | |
| The claustrum's proposed role in consciousness is supported by the effect and target localization of Salvia divinorum. | 2014 | Theoretical or philosophical paper | |
| Total Synthesis of (-)-Salvinorin A. | 2016 | Theoretical or philosophical paper | |
| Salvia Divinorum: entrSalvia divinorum: Entre la prohibición y la construcción de su conocimientoe a proibição e a construção do seu saber | 2022 | Theoretical or philosophical paper | |
| Salvia divinorum induces body awareness changes comparable to metamorphic symptoms in the Alice in Wonderland syndrome | 2019 | Theoretical or philosophical paper |
Citations in the library
Cited by 27
- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. Pharmacological Reviews June 1, 2011
- Salvia divinorum and salvinorin A: an update on pharmacology and analytical methodology. Planta Medica August 1, 2007
- Salvinorin A: allosteric interactions at the mu-opioid receptor. Journal of Pharmacology and Experimental Therapeutics February 1, 2007
- Neo-clerodane diterpenes from the hallucinogenic sage Salvia divinorum. Journal of Natural Products December 1, 2006
- Total synthesis of the hallucinogenic neoclerodane diterpenoid salvinorin A. Organic Letters April 3, 2008
and 22 more in the library
Cites 11
- Salvinorin A, an active component of the hallucinogenic sage salvia divinorum is a highly efficacious kappa-opioid receptor agonist: structural and functional considerations. Journal of Pharmacology and Experimental Therapeutics March 1, 2004
- Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum The Journal of Organic Chemistry November 1, 1984
- Ethnopharmacology of ska María Pastora (Salvia divinorum, Epling and Játiva-M.). Journal of Ethnopharmacology May 1, 1983
- Salvinorin A: the "magic mint" hallucinogen finds a molecular target in the kappa opioid receptor. TIPS - Trends in Pharmacological Sciences March 1, 2003
- Pharmacokinetics of the plant-derived kappa-opioid hallucinogen salvinorin A in nonhuman primates. Synapse December 1, 2005
and 6 more in the library