CannabinoidsCannabisLifestyleCannabinoids Part 4: The Entourage Effect

July 12, 2019by John Cooper

‘With a Little Help from My Friends’ CBN

One person’s oxidation product is another’s therapeutic relief. While generally found only in trace amounts in cannabis, tetrahydrocannabinol (THC) converts to cannabinol (CBN) when exposed to air, heat (160°C/320°F – 180°C/356°F) and/or light over time through an oxidation process1,2. While trying to determine the main psychoactive component of cannabis, researchers isolated CBN, the first isolated cannabinoid3. In the 1930s, its structure was revealed by Dr. Robert Sidney Cahn and it was finally synthesized in the laboratory of Dr. Roger Adams as well as Lord Alexander Todd in 1940. In the years that followed, CBN was found to be only mildly intoxicating with only ¼ the potency of THC.

As a by-product of THC, it also has the ability to bind to the endocannabinoid system (ECS) receptors but has a lower affinity to the CB1 and CB2 receptors. CBN is also able to bind the Transient Receptor Potential Cation Channel Subfamily V Member 2 (TRPV2), which has roles in immunity/inflammation, glucose homeostasis, function of heart cells (cardiomyocytes), and mediating epileptic activity4. The potential therapeutic benefits from isolated CBN is still poorly understood, and most of the studies involve CBN in combination with THC and/or terpenes, which collectively contribute to symptom relief. While there is some evidence for CBN exhibiting sedative qualities, the potential major sedative effects are observed when CBN is consumed along with other cannabinoids and terpenes or the “entourage effect”5. While preliminary studies appear to indicate CBN has promising therapeutic value to moderate epilepsy, inflammation, and bacterial infections, more work needs to be done to elucidate its mechanism of action, effective dosing, and pharmacology6-9. Even though cannabis breeders rarely cultivate high CBN strains, obtaining CBN is relatively easy as long as you are willing to wait (ie. leave a THC strain in a non-airtight container and in the sunlight for a few weeks to months!).

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1. Ross, S.A. & ElSohly, M.A. CBN and D9-THC concentration ratio as an indicator of the age of stored marijuana samples. (United Nations Office on Drugs and Crime 1997).
2. Wang, M. et al. Decarboxylation Study of Acidic Cannabinoids: A Novel Approach Using Ultra-High-Performance Supercritical Fluid Chromatography/Photodiode Array-Mass Spectrometry. Cannabis Cannabinoid Res 1, 262-271 (2016).
3. Pertwee, R.G. Cannabinoid pharmacology: the first 66 years. Br J Pharmacol 147 Suppl 1, S163-71 (2006).
4. Qin, N. et al. TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons. J Neurosci 28, 6231-8 (2008).
5. Karniol, I.G., Shirakawa, I., Takahashi, R.N., Knobel, E. & Musty, R.E. Effects of delta9-tetrahydrocannabinol and cannabinol in man. Pharmacology 13, 502-12 (1975).
6. Russo, E.B. Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. Br J Pharmacol 163, 1344-64 (2011).
7. Turner, C.E., Elsohly, M.A. & Boeren, E.G. Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod 43, 169-234 (1980).
8. Evans, F.J. Cannabinoids: the separation of central from peripheral effects on a structural basis. Planta Med 57, S60-7 (1991).
9. Appendino, G. et al. Antibacterial cannabinoids from Cannabis sativa: a structure-activity study. J Nat Prod 71, 1427-30 (2008).

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