Synthesis of neoclerodane diterpenes and their pharmacological effects.
Kimberly M Lovell, Katherine M Prevatt-Smith, Anthony Lozama, Thomas E Prisinzano
Topics in current chemistry 2011 DOI: 10.1007/128_2010_82 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Review Peer reviewed |
|---|---|
| Topics | Salvia divinorum |
| Keywords | Chemical synthesis Drug discovery Opioid ligands Chiral chemistry |
| Citations | 17 |
| Key findings | Salvinorin A is a non-serotonergic hallucinogen and the first opioid ligand without a basic nitrogen, acting as a kappa opioid receptor agonist. |
Abstract
Salvinorin A is a neoclerodane diterpene that has been shown to be an agonist at kappa opioid receptors. Its unique structure makes it an attractive target for synthetic organic chemists due to its seven chiral centers and diterpene scaffold. This molecule is also interesting to pharmacologists because it is a non-serotonergic hallucinogen, and the first opioid ligand discovered that lacks a basic nitrogen. There have been several total synthesis approaches to salvinorin A, and these will be detailed within this chapter. Additionally, research efforts have concentrated on structure modification of the salvinorin A scaffold through semi-synthetic methods. Most modifications have focused on the manipulation of the acetate at C-2 and the furan ring. However, chemistry has also been developed to generate analogs at the C-1 ketone, the C-4 methyl ester, and the C-17 lactone. The synthetic methodologies developed for the salvinorin A scaffold will be described, as well as specific analogs with interesting biological activities.
Comparable studies
Other narrative reviews on salvia divinorum, most cited first.
| Study | Year | Design | Participants |
|---|---|---|---|
| Here today, gone tomorrow…and back again? A review of herbal marijuana alternatives (K2, Spice), synthetic cathinones (bath salts), kratom, Salvia divinorum, methoxetamine, and piperazines. General (review of novel psychoactive substances) | 2012 | Review | |
| Opioid receptors and legal highs:Salvia divinorumand Kratom | 2008 | Review | |
| Salvinorin A: the "magic mint" hallucinogen finds a molecular target in the kappa opioid receptor. | 2003 | Review | |
| Salvia divinorum and the unique diterpene hallucinogen, Salvinorin (divinorin) A. | 1994 | Review | |
| Drug models of schizophrenia. General (review of drug models of schizophrenia) | 2015 | Review |
Citations in the library
Cited by 5
- Michael acceptor approach to the design of new salvinorin A-based high affinity ligands for the kappa-opioid receptor. European journal of medicinal chemistry October 6, 2014
- Total Synthesis of the Neoclerodane Diterpene Salvinorin A via an Intramolecular Diels–Alder Strategy Organic Letters May 22, 2018
- Salvinorina A: terpeno alucinógeno presente en Salvia divinorum Epling & Játiva Colombia Forense April 10, 2017
- A Protecting-Group-Free Synthesis of (-)-Salvinorin A. Chemistry - A European Journal May 20, 2021
- Pharmacology and anti-addiction effects of the novel κ opioid receptor agonist Mesyl Sal B, a potent and long-acting analogue of salvinorin A. British Journal of Pharmacology 2015
Cites 32
- 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
- Ethnopharmacology of ska María Pastora (Salvia divinorum, Epling and Játiva-M.). Journal of Ethnopharmacology May 1, 1983
- Salvia divinorum and the unique diterpene hallucinogen, Salvinorin (divinorin) A. Journal of Psychoactive Drugs 1994
- Psychopharmacology of the hallucinogenic sage Salvia divinorum. Life Sciences December 22, 2005
and 27 more in the library