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Salvinorin
Group of chemical compounds
Group of chemical compounds
Salvinorins are a group of natural chemical compounds and their structural analogs. Several salvinorins have been isolated from Salvia divinorum. They are classified as diterpenoid furanolactones. Salvinorin A is a hallucinogen with dissociative effects.
Several salvinorins have been isolated and characterized.
| Name | Structure | R1 | R2 | Chemical formula | Molar mass | CAS number | PubChem | ||
|---|---|---|---|---|---|---|---|---|---|
| Salvinorin A | [[File:Salvinorin AB.svg | 120px | right]] | –OCOCH3 | − | C23H28O8 | 432.46 g·mol−1 | 83729-01-5 | |
| Salvinorin B | –OH | − | C21H26O7 | 390.43 g·mol−1 | 92545-30-7 | ||||
| Salvinorin C | [[File:Salvinorin CDEFGH.svg | 120px | right]] | –OCOCH3 | –OCOCH3 | C25H30O9 | 475.29 g·mol−1 | 385785-99-9 | – |
| Salvinorin D | –OH | –OCOCH3 | C23H28O8 | 432.47 g·mol−1 | 540770-13-6 | – | |||
| Salvinorin E | –OCOCH3 | –OH | C23H28O8 | 432.47 g·mol−1 | 540770-14-7 | – | |||
| Salvinorin F | –H | –OH | C21H26O6 | 374.43 g·mol−1 | 540770-15-8 | – | |||
| Salvinorin G | =O | –OCOCH3 | C23H26O8 | 430.45 g·mol−1 | 866622-54-0 | – | |||
| Salvinorin H | –OH | –OH | C21H26O7 | 390.43 g·mol−1 | 872004-62-1 | – | |||
| Salvinorin I | [[File:Salvinorin I.svg | 120px | right]] | – | – | C21H28O7 | 392.45 g·mol−1 | 917951-71-4 | – |
| 17α-Salvinorin J | [[File:17alpha-Salvinorin J.svg | 140px]] | – | – | C23H30O8 | 434.49 g·mol−1 | 1157894-83-1 | – | |
| 17β-Salvinorin J | [[File:17beta-Salvinorin J.svg | 140px]] | – | – | C23H30O8 | 434.49 g·mol−1 | 1157894-85-3 | – |
Occurrence
Originally isolated from S. divinorum, salvinorins are also detected in smaller amounts in:
- Salvia recognita (salvinorin A, 212.9 μg/g)
- Salvia absconditiflora (salvinorin A at 51.5 μg/g, and salvinorin B at 402.2 μg/g)
- Salvia glutinosa (salvinorin A, 38.9 μg/g)
- Salvia potentillifolia (salvinorin B, 2352.0 μg/g)
- Salvia adenocaulon (salvinorin B, 768.8 μg/g)
For comparison, the amount of salvinorin A in S. divinorum ranges from 0.89 to 3.70 mg/g. All fractions reported are based on dry mass.
Interestingly, the above reported species are not very closely related to S. divinorum.
Associated compounds
In search for useful biological activity, several synthetic and semi-synthetic analogs have been prepared for study. Semi-synthetic analogs include salvinorin B ethoxymethyl ether and salvinorin B methoxymethyl ether. Fully synthetic analogs include herkinorin.
Several derivates can be conveniently made from salvinorin B. Most derivatives are selective kappa opioid agonists as with salvinorin A, although some are even more potent, with the most potent compound 2-ethoxymethyl salvinorin B being ten times stronger than salvinorin A. Some derivatives, such as herkinorin, reduce kappa opioid action and instead act as mu opioid agonists.
22-Thiocyanato-salvinorin A is notable because of its functional selectivity. 2-Methoxymethyl Salvinorin B is seven times more potent than Salvinorin A at KOPr in GTP-γS assays.
Many other terpenoids have been isolated from Salvia divinorum, including classes named divinatorins and salvinicins. None of these compounds have shown significant (sub-micromolar) affinity at the kappa-opioid receptor, and there is no evidence that they contribute to the plant's psychoactivity.
References
References
- (November 2017). "Screening of Hallucinogenic Compounds and Genomic Characterisation of 40 Anatolian Salvia Species.". Phytochemical Analysis.
- (2014). "The G-protein biased k-opioid receptor agonist RB-64 is analgesic with a unique spectrum of activities in vivo". J. Pharmacol. Exp. Ther..
- (2008). "2-methoxymethyl-salvinorin B is a potent kappa opioid receptor agonist with longer lasting action in vivo than salvinorin A.". Journal of Pharmacology and Experimental Therapeutics.
- (2006). "Synthesis and in vitro evaluation of salvinorin A analogues: effect of configuration at C(2) and substitution at C(18)". Bioorganic & Medicinal Chemistry Letters.
- (2003). "Divinatorins A-C, new neoclerodane diterpenoids from the controlled sage ''Salvia divinorum''". Journal of Natural Products.
- (2007). "Synthetic studies of neoclerodane diterpenes from ''Salvia divinorum'': exploration of the 1-position". Bioorganic & Medicinal Chemistry Letters.
- (2006). "Synthesis and in vitro pharmacological studies of new C(4)-modified salvinorin A analogues". Bioorganic & Medicinal Chemistry Letters.
- (2003). "Salvinorins D-F, new neoclerodane diterpenoids from ''Salvia divinorum'', and an improved method for the isolation of salvinorin A". Journal of Natural Products.
- (2008). "Standard protecting groups create potent and selective κ opioids: salvinorin B alkoxymethyl ethers". Bioorganic & Medicinal Chemistry.
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