Cannabinoids vs. Cannabimimetic Compounds by Jillian Thayer

June 10 2020 0 Comment(s)

Cannabinoids are compounds found primarily in the cannabis plant that are able to affect components of the endocannabinoid system such as receptors or enzymes. There are two types of cannabinoids: endocannabinoids and phytocannabinoids.

Endocannabinoids are lipid compounds derived from arachidonic acid that the human body generates on demand and where needed. The two most well-researched endocannabinoids are anandamide (N-arachidonoylethanolamine) and 2-AG (2-arachidonoyl glycerol). These neurotransmitters work to keep the body in balance by inhibiting or stimulating physiological processes that can modulate pain, memory, appetite, and more.

Phytocannabinoids refer to plant-derived cannabinoids. These are produced in glandular structures called trichomes from the cannabis plant. These structures contain resin and it consists of phytocannabinoids, terpenes, and other compounds. Phytocannabinoids exist in the plant in their acidic forms which means they contain carboxyl groups. For example, a cannabis plant contains CBDA; the neutral form of CBD occurs through a process called decarboxylation where the carboxyl group in CBDA is eliminated once the plant material has been exposed to sunlight or heat. This happens after the plant is harvested, dried, and processed for end products like concentrated oil or prepared as smokable flowers (decarboxylation will instantly occur here once plant material is ignited and inhaled). 

The two most well-known phytocannabinoids are THC and CBD. Once the compound THC was discovered to be the source of psychoactivity, research has continued to grow to attempt to understand how cannabis works within the body. It has even spurred research to locate other sources of cannabinoids in non-cannabis plants, leading to the discovery of cannabimimetic compounds.  

Cannabimimetic compounds are chemical compounds that mimic cannabis phytocannabinoids by their ability to affect receptors and enzymes from the endocannabinoid system but are not derived from cannabis.  There are a few documented examples of other non-cannabis plants that contain constituents that can work on certain aspects of the endocannabinoid system. This elucidates how complex the endocannabinoid system truly is and it could potentially provide an alternative to cannabis-derived products if certain consumers want to avoid specific compounds. For example, the parent cannabinoid cannabigerol (CBG) has been found in trace amounts in Helichrysum umbraculigerum. The moss liverwort (Radula marginata) contains a constituent called “perrottetinenic acid,” which is structurally similar to THC and can bind to the same cannabinoid receptor in the body as THC. One other well-known cannabimimetic compound is beta-caryophyllene, a sesquiterpene found within cannabis and other aromatic plants. Beta-caryophyllene has an affinity for and binds to the CB2 receptor in the body, which helps provide another route of anti-inflammatory effects. Research is still in the early stages of this work, but it remains to be seen that cannabis isn’t the only unique plant to generate compounds that can affect the endocannabinoid system.

References

Chicca, A., Schafroth, M. A., Reynoso-Moreno, I., Erni, R., Petrucci, V., Carreira, E. M., & Gertsch, J. (2018). Uncovering the psychoactivity of a cannabinoid from liverworts associated with a legal high. Science Advances, 4(10), 1-10. DOI: 10.1126/sciadv.aat2166

Gertsch, J., Leonti, M., Raduner, S., Racz, I., Chen, J. Z., Xie, X. Q., Altmann, K. H., Karsak, M., & Zimmer, A. (2008). Beta-caryophyllene is a dietary cannabinoid. Proceedings of the National Academy of Sciences of the United States of America, 105(26), 9099–9104. https://doi.org/10.1073/pnas.0803601105

Gertsch, J., Pertwee, R. G., & Di Marzo, V. (2010). Phytocannabinoids beyond the Cannabis plant - do they exist?. British journal of pharmacology, 160(3), 523–529. https://doi.org/10.1111/j.1476-5381.2010.00745.x

McPartland, J. M., Guy, G. W., & Di Marzo, V. (2014). Care and feeding of the endocannabinoid system: a systematic review of potential clinical interventions that upregulate the endocannabinoid system. PloS one, 9(3). https://doi.org/10.1371/journal.pone.0089566

Russo E. B. (2019). The Case for the Entourage Effect and Conventional Breeding of Clinical Cannabis: No “Strain,” No Gain. Frontiers in plant science, 9. https://doi.org/10.3389/fpls.2018.01969

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