ChemRxiv
August 19, 2017
Jeremy J Roach, Yusuke Sasano, Cullen L. Schmid et al.
preprint
Salvinorin A (SalA) is a plant metabolite that agonizes the human kappa -opioid receptor (κ-OR) with high affinity and high selectivity over mu- and delta- opioid receptors. Its therapeutic potential has stimulated extensive semi-synthetic studies and total synthesis campaigns. However, structural modification of SalA has been complicated by its instability, and efficient total synthesis has...
Psychopharmacology
August 1, 2017
Amy W M Ewald, Peter J Bosch, Aimee Culverhouse et al.
Kappa-opioid receptor (KOPr) agonists have pre-clinical anti-cocaine and analgesic effects. However, side effects including sedation, dysphoria, aversion, anxiety and depression limit their therapeutic development. The unique structure of salvinorin A has been used to develop longer acting KOPr agonists. We evaluate two novel C-2 analogues of salvinorin A, ethoxymethyl ether Sal B (EOM Sal B)...
Journal of Ethnopharmacology
July 12, 2017
Karina Simón-arceo, Ma Eva González-trujano, Ulises Coffeen et al.
26 citations
Salvia divinorum is a medicinal plant traditionally used in hallucinogenic ethnopharmacological practices and for its analgesic and antinflammatory properties. Its active compounds include diterpenes known as salvinorins which act as potent κ opioid receptor agonists. Given its effects in acute animal models of pain, as well as its antinflammatory attributes, we decided to investigate the...
Journal of Medicinal Chemistry
May 11, 2017
Alexander M. Sherwood, Rachel Saylor Crowley, Kelly F Paton et al.
Previous structure-activity studies on the neoclerodane diterpenoid salvinorin A have demonstrated the importance of the acetoxy functionality on the A-ring in its activity as a κ-opioid receptor agonist. Few studies have focused on understanding the role of conformation in these interactions. Herein we describe the synthesis and evaluation of both flexible and conformationally restricted...
Phytochemistry
May 1, 2017
André R. Cruz, Sara Domingos, Eugenia Gallardo et al.
44 citations
Until the mid-60s, only the Mazatecs, an indigenous group from Oaxaca, Mexico, used Salvia Divinorum (S. divinorum) due to its hallucinogen properties. Later it was found that the hallucinogen effects of this plant were caused by the presence of a neoclerodane diterpene Salvinorin A (salvinorin A), which is a highly selective agonist of kappa-opioid receptor (KOR) that cause more intense...
Colombia Forense
April 10, 2017
Valentina Soto-Restrepo, Gonzalo Taborda Ocampo, William F. Garzón Mendez
Tema y alcance: el objetivo de esta revisión es presentar los estudios químicos que se han realizado sobre Salvia divinorum E&J en estos últimos años. Características: desde la década de 1990 hasta hoy se ha incrementado la distribución y el uso de Salvia divinorum E&J para “fines recreativos”, debido a sus efectos alucinógenos y a su fácil acceso. Sus efectos en el organismo se han relacionado...
European Journal of Pharmacology
April 5, 2017
James Oluwagbamigbe Fajemiroye, Polepally Reddy Prabhakar, Luiz Carlos da Cunha et al.
The increasing cases of depression has made the searches for new drugs and understanding of the underligning neurobiology of this psychiatric disorder a necessity. Here, we modified the structure of salvinorin A (a known halucinogen) and investigated antidepressant-like activity of its four derivatives; 22-methylsulfanylsalvinorin A(SA1), 2-O-cinnamoylsalvinorin B (CSB), 22-azidosalvinorin A...
Fermentation Technology
March 13, 2017
Feridun Gürlek, Eyyüp Taådemir, T. Teker
1 citation
Nowadays, narcotic and enjoyable substances threaten especially adolescents and young people. These substances are fairly common and various. This makes them easier to access. Their use is also closely associated with low socio-economic and socio-cultural conditions. It has been known psychoactive and hallucinogenic effects of Salvia divinorum for many years. It is abused for this purpose. In...
Journal of experimental botany
February 1, 2017
Xiaoyue Chen, Anna Berim, Franck E Dayan et al.
Salvia divinorum (Lamiaceae) is an annual herb used by indigenous cultures of Mexico for medicinal and ritual purposes. The biosynthesis of salvinorin A, its major bioactive neo-clerodane diterpenoid, remains virtually unknown. This investigation aimed to identify the enzyme that catalyzes the first reaction of salvinorin A biosynthesis, the formation of (-)-kolavenyl diphosphate [(-)-KPP],...
Chemistry - A European Journal
December 12, 2016
Nathan J Line, Aaron C Burns, Sean C Butler et al.
41 citations
Salvinorin A (1) is natural hallucinogen that binds the human κ-opioid receptor. A total synthesis has been developed that parlays the stereochemistry of l-(+)-tartaric acid into that of (-)-1 via an unprecedented allylic dithiane intramolecular Diels-Alder reaction to obtain the trans-decalin scaffold. Tsuji allylation set the C9 quaternary center and a late-stage stereoselective chiral...