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High-Potency Cannabis: The Novel Cannabinoid Esters in Cannabis Sativa

A research paper authored by the University of Mississippi presents the discovery and analysis of eleven new cannabinoid esters from a high-potency Cannabis sativa strain. Conducted at the National Center for Natural Products Research and the Departments of Pharmacognosy and Pharmaceutics, this study significantly advances our understanding of cannabis chemistry.


In this groundbreaking study, scientists have discovered these new chemical compounds, known as cannabinoid esters, in a specific high-potency strain of the Cannabis sativa plant. These compounds were identified alongside three already-known cannabinoid acids and the well-known compound Δ9-tetrahydrocannabinol (Δ9-THC).


Using advanced techniques, researchers were able to determine the precise structure of these new compounds, revealing unique combinations of cannabis-derived molecules with various terpenes. These substances contribute to the plant's scent and flavor.


Cannabis sativa, a plant with a long history of human use, offers various applications, from producing fiber and seeds for textiles and food to medicinal uses, thanks to its aromatic resin. The plant's chemical makeup is highly complex, featuring over a hundred cannabinoids, the most famous being Δ9-THC, responsible for its psychoactive effects.


The classification of cannabis into drug, intermediate, and fiber types is based on the Δ9-THC content, demonstrating the plant's versatility. The discovery of these new esters enriches our understanding of cannabis's intricate chemistry and opens new avenues for research and potential applications.


The significance of this discovery extends beyond the scientific curiosity of uncovering new compounds. One of these new esters showed promising antimicrobial properties against a type of fungus, indicating potential medicinal applications. Moreover, this research highlights the vast, untapped potential of high-potency cannabis strains in yielding novel compounds that could lead to new therapeutic agents.


Despite the long history of cannabis research, these findings underscore the plant's continual capacity to surprise and offer new possibilities for medicine, indicating that even well-studied natural sources like cannabis still hold secrets waiting to be discovered.


Let's dig deeper:


Discovery of New Esters:


Researchers report the isolation and detailed analysis (structure elucidation) of eleven previously unknown esters from a high-potency cannabis variety. Esters are chemical compounds formed by replacing the hydrogen of an acid with an alkyl or other organic group. Many esters are derived from carboxylic acids, and in the context of cannabis, these new esters are modifications of cannabinoids, the active chemical compounds in cannabis.

These compounds are named based on their chemical structure, indicating the type of terpene (a large and diverse class of organic compounds produced by a variety of plants) attached to the cannabinoid base molecule (like Δ9-tetrahydrocannabinol or cannabigerol).


List of New Esters: The newly discovered esters include:


  • β-fenchyl Δ9-tetrahydrocannabinolate

  • epi-bornyl Δ9-tetrahydrocannabinolate

  • α-terpenyl Δ9-tetrahydrocannabinolate

  • 4-terpenyl Δ9-tetrahydrocannabinolate

  • α-cadinyl Δ9-tetrahydrocannabinolate

  • γ-eudesmyl Δ9-tetrahydrocannabinolate

  • γ-eudesmyl cannabigerolate

  • 4-terpenyl cannabinolate

  • bornyl Δ9-tetrahydrocannabinolate

  • α-fenchyl Δ9-tetrahydrocannabinolate

  • α-cadinyl cannabigerolate These compounds are named based on their chemical structure, indicating the type of terpene (a large and diverse class of organic compounds produced by a variety of plants) attached to the cannabinoid base molecule (like Δ9-tetrahydrocannabinol or cannabigerol).

    • Isolation of Known Cannabinoids: In addition to the new esters, the study also isolated four well-known cannabinoids:

    • Δ9-tetrahydrocannabinol (Δ9-THC)

    • Δ9-tetrahydrocannabinolic acid A (Δ9-THCA)

    • Cannabinolic acid A (CBNA)

    • Cannabigerolic acid (CBGA) These cannabinoids are recognized for their roles in the plant's effects on the human body, with Δ9-THC being particularly noted for its psychoactive properties. Evaluation of Isolated Compounds: All isolated compounds, both the newly discovered esters and the known cannabinoids, were tested for antimicrobial and antimalarial activities, as well as their ability to bind to the CB-1 receptor. The CB-1 receptor is a critical component of the human endocannabinoid system, regulating various physiological processes. The binding affinity of cannabinoids to the CB-1 receptor significantly influences their effects on the body.


Identifying the specific mono- and sesquiterpene components within these cannabinoid esters involved a thorough investigation to check if such terpenes had been previously detected in Cannabis. This task proved challenging due to the vague nature of past identifications.


For instance, although fenchol has been mentioned in eight studies as a component of cannabis volatile oils, only two of these studies specify it as β-fenchol, with no reports on α-fenchol. Similarly, while several reports exist for borneol, they all refer to the (±)-endo-borneol variety, with none mentioning the C-1″ epimer of borneol discovered in this study. The compound (±)-α-Terpineol is widely documented, yet only a couple of studies specify its exact structure as (−)-(S), identified through GC-MS analysis.


Reports on (±)-4-Terpineol and cadinol are also vague about their stereochemistry, though our research identified certain esters as α-cadinol esters based on GC-MS library comparisons. Previous literature does mention γ-Eudesmol.


Despite the extensive research on cannabis over the last forty years, our study represents the first detailed chemical examination of a high-potency cannabis strain and the discovery of new cannabinoid compounds since 1995.


This suggests that the unique potency of this cannabis material may lead to uncovering further novel metabolites.


Isn't this fascinating news? It's not news. It's from 2008, and information that every single person selling THC should know about and every single 'expert' in the industry should know of, but so few do, and this is why people are suffering from Endocannabinoid System Dysfunctions that many of the same people call a 'High Tolerance.'


If we don't know the constituents of the plant, and we don't know the eight main endocannabinoids - then we're like blind people trying to play baseball with no bat. We're not in the game, we can't see what we're doing, and if we swing too hard, someone is going to get hurt.


This is a 2008 study!



Wow, we've still got a lot to learn!


 


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