Short synthesis of a novel class of salvinorin A analogs with hemiacetalic structure.
Ruslan V Bikbulatov, Jeremy Stewart, Wentao Jin, Feng Yan, Bryan L. Roth, Daneel Ferreira, Jordan K Zjawiony
Tetrahedron Letters February 4, 2008 DOI: 10.1016/j.tetlet.2007.12.041 (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 | New semisynthetic salvinorin A analogs with an unusual hemiacetal structure were prepared, formed with epimerization at C-12 while preserving salvinorin A's original configuration. The dimethyl ester derivative of the hemiacetal showed affinity for both the κ-opioid receptor (KOR) and the μ-opioid receptor (MOR), unlike salvinorin A's KOR selectivity. |
Abstract
Novel semisynthetic analogs of salvinorin A, a full agonist having extraordinary affinity as well as selectivity for the κ-opioid receptor (KOR), were obtained in good yields. The derivatives are remarkable for their unusual and unique hemiacetal structure in the salvinorin series of compounds. The formation of the hemiacetal occurs with epimerization at C-12, thus preserving the original configuration of salvinorin A. The dimethyl ester derivative of the hemiacetal was found to have an affinity for both KOR and MOR (μ-opioid receptor).
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 7
- Neuropharmacology of the naturally occurring kappa-opioid hallucinogen salvinorin A. Pharmacological Reviews June 1, 2011
- Synthesis of neoclerodane diterpenes and their pharmacological effects. Topics in current chemistry 2011
- Investigating the Effects of Novel Kappa Opioid Receptor Agonists on the Dopamine Transporter 2011
- Solving an Old Puzzle: Elucidation and Evaluation of the Binding Mode of Salvinorin A at the Kappa Opioid Receptor Preprints.org November 1, 2022
- Synthesis and biological evaluation of C-2 halogenated analogs of salvinorin A. Bioorganic & Medicinal Chemistry Letters October 1, 2010
and 2 more in the library
Cites 15
- Salvinorin A: a potent naturally occurring nonnitrogenous kappa opioid selective agonist. Proceedings of the National Academy of Sciences September 3, 2002
- Divinorin A, a psychotropic terpenoid, and divinorin B from the hallucinogenic Mexican mint, Salvia divinorum The Journal of Organic Chemistry November 1, 1984
- Salvia divinorum and the unique diterpene hallucinogen, Salvinorin (divinorin) A. Journal of Psychoactive Drugs 1994
- Salvinorin C, a new neoclerodane diterpene from a bioactive fraction of the hallucinogenic Mexican mint Salvia divinorum. Organic Letters November 29, 2001
- Salvinorin A: allosteric interactions at the mu-opioid receptor. Journal of Pharmacology and Experimental Therapeutics February 1, 2007
and 10 more in the library