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Guide to Cannabinoids

Learn all about cannabinoids in Natural Kore’s Guide to Cannabinoids!

What are cannabinoids?

Phytocannabinoids, or simply called cannabinoids, are the naturally occurring compounds found in a few plants, but most abundantly in Cannabis sativa. There are over 100 known natural cannabinoids found in C. sativa, with Δ9-tetrahydrocannabinol (THC) and cannabidiol (CBD) being the most prominent and well-studied. Cannabinoids are in part responsible for the medicinal and psychoactive effects Cannabis can provide.

What is the endocannabinoid system?

Cannabinoids interact with the human body through the endocannabinoid system (ECS). The ECS is a neuron regulatory system made up of endocannabinoids (cannabinoids naturally produced by the human body), receptors (named CB1 and CB2) and enzymes that aid the body in maintaining homeostasis. This involves regulating an array of body systems, including pain, memory, mood and appetite.

Within the ECS, cannabinoid receptors can be found on the surface of specific cells. The primary endocannabinoid receptors are CB1 and CB2. CB1 receptors are prevalent in the brain but are found in other locations like kidney, liver and lung tissue. CB2 receptors are found outside the nervous system in peripheral tissue (for example, heart cells, bone cells, and immune cells like leukocytes, lymphocytes and macrophages). The receptors found in the cell membrane and are proteins that bind to signal molecules near the surface of the cell thus responding to chemical changes outside of the cell. The endocannabinoids and phytocannabinoids, along with synthetic cannabinoids, are specific signal molecules for CB1 and CB2 receptors. Once the cannabinoid binds to the receptor, the “signal” is transmitted across the membrane causing the appropriate cellular response. For example, the CB1 receptors bind with the phytocannabinoid THC to produce the psychoactive effect commonly associated with Cannabis. The CB2 receptors bind to cannabinoids like CBD and THC, which leads to enhancing the immune system by aiding in anti-inflammatory responses, digestion, and neuroprotection. For both receptors, there are other regulatory effects that contribute to the reported medicinal properties of cannabinoids, like CBD treatment for certain epileptic seizures. [1]

Important Cannabinoids

THC (Δ9–tetrahydrocannabinol)

Molecular formulaC21H30O2
Molecular weight314.5 g/mol
CAS Number (Chemical Abstracts Service number)1972-08-3

THC is the most well known phytocannabinoid, and that is because it is the one of the few cannabinoids that possesses the psychoactive effect that lead to the euphoric and calming feeling. THC binds with CB1 receptors in the brain which causes changes in the levels of various dopamine and epinephrine neurotransmitters leading to produce reported effects including euphoria, relaxation, and increased self-awareness. In a medical context, THC can improve digestion, provide pain relief and enhance mood. Although, THC has been used to treat medical disorders ranging from Parkinson’s disease to sleep apnea, scientific studies need be expanded to provide robust and sound research to establish whether there is clear evidence demonstrating effectiveness for various disorders.[2]

THC (Δ9–tetrahydrocannabinol)

 

CBD (cannabidiol)

Molecular formulaC21H30O2
Molecular weight314.5 g/mol
CAS Number13956-29-1

CBD differs from THC in that it does not produce psychoactive effects. Instead, CBD primarily binds to the CB2 receptors found throughout the body. It binds weakly to the CB1 receptor, and it has been reported to dampen the effects of THC. CBD demonstrates analgesic (pain relieving), anti-inflammatory, and antineoplastic (inhibits tumor growth) activities. Some of CBD’s physiological benefits include reduced stress, a better appetite and improved sleep.[3]

An FDA-approved drug, natural CBD, but produced by pharmaceutical companies, has been an effective treatment for epileptic seizures. It should be noted here that the chemical structure of Epidiolex is the same as the chemical structure of CBD. Epidiolex is pure CBD, while many products, but not all products on the market, are usually a plant extract that contains other cannabinoids and terpenes.[4] Many use topical CBD for pain and discomfort, but oral or inhaled CBD hemp for pain and stress as well. Cannabis sativa that produces less than 0.3% THC on a dry-weight basis is considered hemp and is legal based on the 2018 Federal Farm Bill.[5] Our products use hemp CBD that have been tested at an accredited analytical lab.

CBD (Cannabidiol)

CBN (cannabinol)

Molecular formulaC21H26O2
Molecular weight310.4 g/mol
CAS Number521-35-7

CBN is a cannabinoid found in low amounts. It is mildly psychoactive and much less potent than THC (approximately 2-10 times less potent, according to various research studies). CBN is derived from THC and is naturally formed when THC is exposed to oxygen, heat and light during the plant drying process after harvesting. Thus, as dry Cannabis plant material ages the THC level will decrease slowly while CBN levels increase, and the overall psychoactive effects of the plant will decrease as the amount of THC decreases. [6]

CBN (Cannabinol)

CBG (cannabigerol)

Molecular formulaC21H32O2
Molecular weight316.5 g/mol
CAS Number25654-31-3

CBG is a non-psychoactive cannabinoid and is generally found in very small quantities in most cannabis strains. CGBA is the parent molecule to THCA and CBDA, which are non-biologically converted, via decarboxylation, to THC and CBD, respectively. CBG is the direct decarboxylated product of CBGA. Scientists/breeders are breeding Cannabis strains to obtain higher yields of CBG and further testing the cannabinoid to examine its role as an appetite enhancer, a cannabinoid receptor agonist (like THC and CBD), an anti-inflammatory agent, an antibacterial agent, a neuroprotective agent and an antioxidant. [7]

CBG (Cannabigerol)

CBC (cannabichromene)

Molecular formulaC21H30O2
Molecular weight314.5 g/mol
CAS Number20675-51-8

CBC binds weakly to the CB1 receptors in the brain, and thus is non-psychoactive. CBC has been shown to spur neurogenesis and brain growth. CBC also has demonstrated strong anti-cancer and anti-tumor capabilities. CBC does bind well to CB2 receptors, driving anti-inflammatory activities.[8] Other conditions CBC has shown promise treating include irritable bowel syndrome, Crohn’s disease and post-operative pain. [9]

CBC (Cannabichromene)

THCV (tetrahydrocannabivarin)

Molecular formulaC19H26O2
Molecular weight286.4 g/mol
CAS Number31262-37-0

THCV has an almost identical molecular structure to Δ9-THC, differing only by the length of its lipophilic (“fatty”) alkyl (linear carbon) chain. Although possessing similar psychoactive properties as THC, the difference in THCV’s structure results in an array of different effects. THC demonstrates its effects through weak partial agonist activity of both CB1 and CB2 receptors, THCV acts as a CB1 antagonist and a partial agonist of CB2

One such difference of the effects of THC versus THCV is that THCV acts as an appetite suppressant. THCV has been shown to help reduce stress and fight anxiety, becoming a potent treatment for dealing with PTSD. [10]

THCV (Tetrahydrocannabivarin)

CBDV (cannabidivarin)

Molecular formulaC19H26O2
Molecular weight286.4 g/mol
CAS Number24274-48-4

Just like CBD, CBDV is non-psychoactive. The majority of the research on CBDV revolves around its benefits in dealing with seizures. GW Pharmaceuticals, which developed the first FDA-approved CBD drug called Epidiolex, is actively developing a CBDV-based drug known as GPW42006 to reduce or prevent epileptic and other forms of seizures, similar to the effects of CBD/Epidiolex. [11]

CBDV (Cannabidivarin)

References

[1] – Lu, Hui-Chen, and Ken Mackie. “An Introduction to the Endogenous Cannabinoid System.” Biological Psychiatry vol. 79,7 (2016): 516-25. doi:10.1016/j.biopsych.2015.07.028

[2] – National Center for Biotechnology Information. “PubChem Compound Summary for CID 16078, Dronabinol” PubChemhttps://pubchem.ncbi.nlm.nih.gov/compound/Dronabinol. Accessed 30 April, 2021.

[3] – National Center for Biotechnology Information. “PubChem Compound Summary for CID 644019, Cannabidiol” PubChemhttps://pubchem.ncbi.nlm.nih.gov/compound/Cannabidiol. Accessed 30 April, 2021.

[4] – FDA Regulation of Cannabis and Cannabis-Derived Products, Including Cannabidiol (CBD). Content current as of: 01/22/2021. https://www.fda.gov/news-events/public-health-focus/fda-regulation-cannabis-and-cannabis-derived-products-including-cannabidiol-cbd

[5] – Testimony Hemp Production and the 2018 Farm Bill. July 2019. https://www.fda.gov/news-events/congressional-testimony/hemp-production-and-2018-farm-bill-07252019. Accessed 30 April, 2021.

[6] – Ethan B. Russo, Jahan Marcu, “Chapter Three – Cannabis Pharmacology: The Usual Suspects and a Few Promising Leads”, Volume 80, 2017, Pages 67-134. https://www.sciencedirect.com/science/article/abs/pii/S1054358917300273

[7] – National Center for Biotechnology Information. “PubChem Compound Summary for CID 5315659, Cannabigerol” PubChemhttps://pubchem.ncbi.nlm.nih.gov/compound/Cannabigerol. Accessed 30 April, 2021.

[8] – Udoh, Michael et al. “Cannabichromene is a cannabinoid CB2 receptor agonist.” British journal of pharmacology vol. 176,23 (2019): 4537-4547. doi:10.1111/bph.14815

[9] – Leinwand, Kristina L et al. “Manipulation of the Endocannabinoid System in Colitis: A Comprehensive Review.” Inflammatory bowel diseases vol. 23,2 (2017): 192-199. doi:10.1097/MIB.0000000000001004

[10] – Abioye, A., Ayodele, O., Marinkovic, A. et al. Δ9-Tetrahydrocannabivarin (THCV): a commentary on potential therapeutic benefit for the management of obesity and diabetes. J Cannabis Res 2, 6 (2020). https://doi.org/10.1186/s42238-020-0016-7

[11] – “GW Pharmaceuticals Initiates Phase 2 Clinical Study of Cannabidivarin (CBDV) in Epilepsy”. https://ir.gwpharm.com/news-releases/news-release-details/gw-pharmaceuticals-initiates-phase-2-clinical-study. Accessed 30 April, 2021.

General References

National Academies of Sciences, Engineering, and Medicine; Health and Medicine Division; Board on Population Health and Public Health Practice; Committee on the Health Effects of Marijuana: An Evidence Review and Research Agenda. The Health Effects of Cannabis and Cannabinoids: The Current State of Evidence and Recommendations for Research. Washington (DC): National Academies Press (US); 2017 Jan 12. 4, Therapeutic Effects of Cannabis and Cannabinoids. Available from: https://www.ncbi.nlm.nih.gov/books/NBK425767/

All chemical data from https://pubchem.ncbi.nlm.nih.gov/