Salvia Chemistry

Salvia Divinorum Chemistry

For many generations the Mazatec Indians of the Oaxaca Mountains of Mexico have harvested salvia divinorum for use in their ceremonies as a divination tool. Botanist Jean Basset Johnson conducted field research in the 30’s and began to share this miraculous plant with the rest of the world. Salvia divinorum possesses very powerful psychotropic properties and is considered as the most unique of among the nearly 1,000 different salvia species. Salvia divinorum contains a substance known as salvinorin. This diterpene compound (in laymen’s term it only contains carbon, hydrogen and oxygen atoms) is present as salvinorin A (at 96%) and B (at 4%). Morphine, for example, contains carbon, hydrogen, oxygen, and nitrogen. While salvinorin B is not known to have any psychoactive effects, salvinorin A, which is abundant in salvia divinorum, is known to be the most potent natural psychoactive substance known to man.

Chemical Composition

Salvia divinorum cannot be classified as a drug due to a couple of important reasons. For one, salvinorin A does not contain any opiates when broken down. Salvinorin doesn’t contain alkaloids either. Both are what all drug tests look for. Alkaloids contain nitrogen atoms (which are exactly what shows up positive on a drug test.) Salvinorin is a diterpene which contains no nitrogen.  Basically, if you had to take a urine test, salvia would not produce a positive result for either opiates, or other alkaloid drugs. The chemical composition, however is quite complicated, as explained below from the European Monitoring Centre for Dugs and Drug Addiction journal on salvinorin A:

“The chemical identification of the psychoactive principle of Salvia divinorum was completed simultaneously by Ortega and Valdés in the early 1980s. The main ingredient responsible for the psychoactive effect of the plant is a neoclerodane diterpene called salvinorin A. The IUPAC systematic name is (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(acetyloxy)-2-(3-furanyl)dodecahydro-6a,10b-dimethyl-4,10-dioxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester (CAS number: 83729-01-5). Unlike classical natural or synthetic hallucinogens, salvinorin A does not contain a nitrogen atom — it is not an alkaloid. The dried leaves, leaf extracts and pure salvinorin A are stable at ambient temperature in the absence of light or air, although there is no systematic study on this. Salvinorin A is unstable in basic solutions and is soluble in conventional organic solvents, including acetone, acetonitrile, chloroform, dimethyl sulfoxide and methanol, but is essentially insoluble in hexane and water.” (EMCDDA, 2015)

Molecular Structure

Molecular formula: C₂₃H₂₈O₈
Molecular weight: 432.47 g/mol

Physical Form

In the natural structure, salvia divinorum is a shrub-like plant, native to the lamiaceae (or mint family). It grows to 0.05m to 1.50 meters in height, and has a square-like, hollow stem with opposing pairs of ovate-lanceolate, jagged-edged leaves, which are occasionally described as velvety or hairy in appearance. The characteristic flower of the plant has a white corolla surrounded by a violet blue calyx. Salvia divinorum rarely ever germinates, or produces seeds, and even when they are produced, they are hardly ever viable for growing another plant from and that is why the propagation of the plant is exclusively vegetative and most of the Salvia divinorum plants now cultivated worldwide are mere clones of a few selections from the early Oaxaca collections. Pure salvinorin A forms colorless crystals with a melting point of 242–244 ^oC.

Pharmacology

Salvinorin A has a unique mode of action and pharmacology. The potent and selective full agonist activity at k-opioid receptor (KOR) subtypes is primarily responsible for the hallucinogenic effect of the drug. There are three main opioid receptor groups: mu, kappa, and delta. Different reactions will occur depending on which receptor is triggered.  Research has shown that salvinorin A is a potent κ-opioid (kappa) receptor agonist; meaning that it binds to the receptor and triggers a response by the corresponding cell. Agonists often have the same effect as a naturally occurring substance. The κ-opioid receptor is a protein and one of five receptors that bind opium-like compounds in the brain, controlling the effects of said compounds (including mood, consciousness, motor control, and pain). It also is the main receptor associated with visual hallucinations. Where the ‘classical’ hallucinogens found in psilocybin, mushrooms and LSD are all alkaloidal in nature and therefore interact with specific serotonin receptor subtypes. Morphine, for example, contains carbon, hydrogen, oxygen, and nitrogen. Since salvinorin A only has carbon, hydrogen, and oxygen, it is cannot be broken down into salt, unlike opiates. Salvinorin A shows no significant binding to over 50 other (psycho)pharmacologically important receptors, transporter proteins and ion channels.

“In humans, salvinorin A is known to cause rather short-lived, yet extremely profound hallucinations. Inhalation of doses equivalent to 200–500 micrograms leads to loss of control over physical movements (incapacitation); uncontrollable laughter; vivid, colorful and often bizarre, dream- or film-like hallucinations. Temporal boundaries among past, present and future disappear and the user is transported to alternative time and places (‘spatiotemporal dislocation’) with perceptions of being in several locations simultaneously. The ‘trip’, especially at higher doses, can be frightening and can cause serious psychotic disturbances. It has been reported that this can last for hours after the hallucinations have disappeared. Common after-effects include tiredness, dizziness and amnesia. Emergency reports have described lasting psychosis in vulnerable individuals.” (EMCDDA, 2015)