Salvinorins are a group of natural chemical compounds and their

structural analog A structural analog (analogue in modern traditional English; Commonwealth English), also known as a chemical analog or simply an analog, is a compound having a structure similar to that of another compound, but differing from it in respect to a ...

s. Several salvinorins have been isolated from ''

Salvia divinorum ''Salvia divinorum'' (Latin: "sage of the diviners"; also called ska maría pastora, seer's sage, yerba de la pastora, magic mint or simply salvia) is a plant species with transient psychoactive properties when its leaves are consumed by che ...

''. They are classified as

diterpenoid Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...

furanolactone A furanolactone is a heterocyclic chemical compound that contains both a lactone Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbo ...

Salvinorin A Salvinorin A is the main active psychotropic molecule in ''Salvia divinorum''. Salvinorin A is considered a dissociative hallucinogen. It is structurally distinct from other naturally occurring hallucinogens (such as DMT, psilocybin, and m ...

is a hallucinogen with dissociative effects. Several salvinorins have been isolated and characterized.

Occurrence

Originally isolated from ''S. divinorum'', salvinorins are also detected in smaller amounts in: * ''

Salvia recognita ''Salvia recognita'' is a woody-based perennial that is endemic to central Turkey, typically growing in light shade at the base of cliffs, at elevations of less than . It contains a low concentration of salvinorin A, at approximately 213 microgra ...

'' (salvinorin A, 212.9 μg/g) * ''

Salvia absconditiflora ''Salvia absconditiflora'' is a perennial plant species of the family Lamiaceae. It is endemic to Turkey. It contains Salvinorin A at a concentration of 51.5 micrograms In the metric system, a microgram or microgramme is a unit of mass equal ...

'' (salvinorin A at 51.5 μg/g, and salvinorin B at 402.2 μg/g) * ''

Salvia glutinosa ''Salvia glutinosa'', the glutinous sage, sticky sage, Jupiter's sage, or Jupiter's distaff, is a herbaceous perennial plant belonging to the family Lamiaceae. Description ''Salvia glutinosa'' grows to approximately tall.Pignatti S. - Flora d' ...

'' (salvinorin A, 38.9 μg/g) * ''

Salvia potentillifolia ''Salvia'' () is the largest genus of plants in the sage family Lamiaceae, with nearly 1000 species of shrubs, herbaceous perennials, and annuals. Within the Lamiaceae, ''Salvia'' is part of the tribe Mentheae within the subfamily Nepetoid ...

'' (salvinorin B, 2352.0 μg/g) * ''

Salvia adenocaulon ''Salvia'' () is the largest genus of plants in the sage family Lamiaceae, with nearly 1000 species of shrubs, herbaceous perennials, and annuals. Within the Lamiaceae, ''Salvia'' is part of the tribe Mentheae within the subfamily Nepetoid ...

'' (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 Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...

have been prepared for study. Semi-synthetic analogs include

salvinorin B ethoxymethyl ether Salvinorin B methoxymethyl ether (2-''O''-methoxymethylsalvinorin B) is a semi-synthetic analogue of the natural product salvinorin A used in scientific research. It has a longer duration of action of around 2–3 hours, compared to less than 30 ...

and

salvinorin B methoxymethyl ether Salvinorin B methoxymethyl ether (2-''O''-methoxymethylsalvinorin B) is a semi-synthetic analogue of the natural product salvinorin A used in scientific research. It has a longer duration of action of around 2–3 hours, compared to less than 30 ...

. Fully synthetic analogs include

herkinorin Herkinorin is an opioid analgesic that is an analog (chemistry), analogue of the natural product salvinorin A. It was discovered in 2005 during structure-activity relationship studies into neoclerodane diterpenes, the family of chemical compounds ...

. Several

derivate Derivatization is a technique used in chemistry which converts a chemical compound into a product (the reaction's derivate) of similar chemical structure, called a derivative. Generally, a specific functional group of the compound participates ...

s can be conveniently made from salvinorin B. Most derivatives are selective kappa opioid

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

s 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

, reduce kappa opioid action and instead act as mu opioid agonists. 22-Thiocyanato-salvinorin A is notable because of its

functional selectivity Functional selectivity (or “agonist trafficking”, “biased agonism”, “biased signaling”, "ligand bias" and “differential engagement”) is the ligand-dependent selectivity for certain signal transduction pathways relative to a referen ...

. 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

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