Salvinorin
Template:Short description Template:Missing information 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 | –OCOCH3 | − | C23H28O8 | 432.46 g·mol−1 | 83729-01-5 | Template:PubChem | |
| Salvinorin B | –OH | − | C21H26O7 | 390.43 g·mol−1 | 92545-30-7 | Template:PubChem | |
| Salvinorin C | –OCOCH3 | –OCOCH3 | C25H30O9 | 475.29 g·mol−1 | 385785-99-9 | – | |
| Salvinorin D<ref name=Munro2003/> | –OH | –OCOCH3 | C23H28O8 | 432.47 g·mol−1 | 540770-13-6 | – | |
| Salvinorin E<ref name=Munro2003/> | –OCOCH3 | –OH | C23H28O8 | 432.47 g·mol−1 | 540770-14-7 | – | |
| Salvinorin F<ref name=Munro2003/> | –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 | – | – | C21H28O7 | 392.45 g·mol−1 | 917951-71-4 | – | |
| 17α-Salvinorin J | File:17alpha-Salvinorin J.svg | – | – | C23H30O8 | 434.49 g·mol−1 | 1157894-83-1 | – |
| 17β-Salvinorin J | File:17beta-Salvinorin J.svg | – | – | 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)<ref name="Anatolia">Template:Cite journal</ref>
- Salvia absconditiflora (salvinorin A at 51.5 μg/g, and salvinorin B at 402.2 μg/g)<ref name="Anatolia"/>
- Salvia glutinosa (salvinorin A, 38.9 μg/g)<ref name="Anatolia"/>
- Salvia potentillifolia (salvinorin B, 2352.0 μg/g)<ref name="Anatolia"/>
- Salvia adenocaulon (salvinorin B, 768.8 μg/g)<ref name="Anatolia"/>
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.<ref name="Anatolia"/>
Interestingly, the above reported species are not very closely related to S. divinorum.<ref name="Anatolia"/>
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.<ref name=Munro2008/><ref name=Holden2007/><ref name=Lee2006/><ref name=Beguin2006/>
22-Thiocyanato-salvinorin A is notable because of its functional selectivity.<ref name="pmid25320048">Template:Cite journal</ref> 2-Methoxymethyl Salvinorin B is seven times more potent than Salvinorin A at KOPr in GTP-γS assays.<ref>Template:Cite journal</ref>
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.<ref name=Bigham2003/><ref name=Munro2003/>