Understanding Terpenes, Cannabinoids, and Flavonoids

Research continues to provide evidence that there are many factors that go into how strains affect a person – more than just levels of THC.

This course details a few of the many chemical compounds responsible for cannabis’ effects and provides examples of methods for administering medical cannabis. Also, this course makes it easy to understand this information so you can choose the most effective cannabis products to address your individual needs.

Cannabis is a very complex plant with hundreds of chemical compounds whose benefits are continually researched and discovered.

While you may have heard of cannabinoids, the most common of which are THC and CBD, some of the other compounds found in cannabis are terpenes. Both cannabinoids and terpenes have the ability to influence and alter the effects of cannabis.

There are over 100 unique terpenes that have been identified to date in the cannabis plant, and each one contributes to a different scent and sensory experience.

Terpenes are for the most part volatile, aromatic oils and are the most common plant-based chemical in nature. They are what give plants their distinctive fragrance. Many serve a protective function for the plants by deterring herbivores. Essential oils are made up primarily of terpenes.

So what do terpenes in cannabis do?

Cannabis terpenes are produced in the trichomes, the same glands that produce the cannabinoids. They are responsible for the aromatic properties of cannabis. Along with producing a distinctive aroma, they can also serve a therapeutic purpose. Cannabis varieties with very similar cannabinoid profiles can have vastly different psychoactive and therapeutic effects. This might be due to the variation in terpenes. Although terpenes and essential oils are well known to aromatherapists, perfumers, and herbalists, cannabis researchers are just now starting to study the medicinal properties of these hydrocarbons.¹

Below is a brief description of the most common cannabis terpenes:

Alpha-Pinene is the most common terpene in the plant world. It is what gives conifers their aroma and is also found in rosemary and basil. It is often found in cannabis, is a bronchodilator and has been used in the treatment of asthma. It promotes alertness, is anti-inflammatory and helps with short-term memory retention.

Beta-caryophyllene is a terpene that is also considered to be a dietary cannabinoid because it interacts with receptors in the endocannabinoid system. It is common in black pepper, oregano, green leafy vegetables and other edible herbs, as well as cannabis. Its aroma is spicy, woody and peppery. It is a powerful anti-inflammatory, both internally and externally.

Humulene is found in hops, Vietnamese coriander and cannabis. It is anti-tumor, anti-inflammatory and suppresses appetite.

Limonene is found in citrus, peppermint, and rosemary, as well as cannabis. It is the main active ingredient in citrus cleaners. It is associated with strains that have a quick onset and may be able to treat gastric reflux. It also has powerful antimicrobial properties.

Linalool is prominent in lavender, rosewood, birch and many other plants. Its aroma is floral and can smell slightly of candy. It has sedative, analgesic, anti-convulsant, and anti-epileptic properties and can help with stress.

Myrcene is found in mangos, hops, lemongrass and cannabis. Its aroma is earthy, herbal and sometimes fruity. It is very sedative, increases the effects of other sedative medicines and is a muscle relaxant. It can help with insomnia, inflammation, muscle tension and pain. It is much more common in indica strains than in sativa strains but most strains contain some Myrcene.

 


 

¹Fischedick J, E. (2015). Cannabinoids and Terpenes as Chemotaxonomic Markers in Cannabis. Natural Products Chemistry & Research, [online] 03(04). Available at: https://www.researchgate.net/publication/281006045_Cannabinoids_and_Terpenes_as_Chemotaxonomic_Markers_in_Cannabis [Accessed 28 Oct. 2017].

CBG, or Cannabigerol, is non-psychoactive and non-intoxicating “parent” of other cannabinoids. CBG is synthesized and is then converted to the other cannabinoids through processes internal to the cannabis plant.

CBG has been studied for its potential for the treatment of pain¹, skin conditions², and inflammatory bowel disease³, among other medical ailments.

 


 

¹Russo, E. (2011). Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. British Journal of Pharmacology, [online] 163(7), pp.1344-1364. Available at: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3165946.

²Oláh, A., Markovics, A., Szabó-Papp, J., Szabó, P., Stott, C., Zouboulis, C. and Bíró, T. (2016). Differential effectiveness of selected non-psychotropic phytocannabinoids on human sebocyte functions implicates their introduction in dry/seborrhoeic skin and acne treatment. Experimental Dermatology, [online] 25(9), pp.701-707. Available at: https://www.ncbi.nlm.nih.gov/pubmed/27094344.

³Borrelli, F., Fasolino, I., Romano, B., Capasso, R., Maiello, F., Coppola, D., Orlando, P., Battista, G., Pagano, E., Di Marzo, V. and Izzo, A. (2013). Beneficial effect of the non-psychotropic plant cannabinoid cannabigerol on experimental inflammatory bowel disease. Biochemical Pharmacology, 85(9), pp.1306-1316.

CBN (Cannabinol) is an oxidative degradation product of THC (oxidation happens when something is exposed to oxygen). While noted for its use with sleep disorders when combined with THC¹, it is commonly considered a weak psychoactive (with some studies measuring slight psychoactive properties², while others suggesting that it has none³).

CBC (Cannabichromene) is another cannabinoid, and though less commonly known it is actually one of the more prevalent cannabinoids found in young cannabis plants⁴. CBC has been found to interact with receptors differently than other cannabinoids⁵, and also to be an antibacterial⁶ and provide sedative effects – including anti-depressant effects⁷.

 


 

¹Russo, E. (2011). Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. British Journal of Pharmacology, [online] 163(7), pp.1344-1364. Available at: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3165946/pdf/bph0163-1344.pdf [Accessed 14 Oct. 2017].

²Karniol, I., Shirakawa, I., Takahashi, R., Knobel, E. and Musty, R. (1975). Effects of &Delta;<sup>9</sup>-Tetrahydrocannabinol and Cannabinol in Man. Pharmacology, [online] 13(6), pp.502-512. Available at: https://www.karger.com/Article/Abstract/136944 [Accessed 14 Oct. 2017].

³Dalterio, S., Mayfield, D., Bartke, A. and Morgan, W. (1985). Effects of psychoactive and non-psychoactive cannabinoids on neuroendocrine and testicular responsiveness in mice. Life Sciences, [online] 36(13), pp.1299-1306. Available at: https://www.ncbi.nlm.nih.gov/pubmed/2984499.

⁴Harvey, D. and Brown, N. (1990). In vitro metabolism of cannabichromene in seven common laboratory animals. Drug Metabolism and Disposition, [online] 18(6). Available at: http://dmd.aspetjournals.org/content/18/6/1065.long; https://www.ncbi.nlm.nih.gov/pubmed/1981514 [Accessed 14 Oct. 2017].

⁵Aizpurua-Olaizola, O., Soydaner, U., Öztürk, E., Schibano, D., Simsir, Y., Navarro, P., Etxebarria, N. and Usobiaga, A. (2016). Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes. Journal of Natural Products, [online] 79(2), pp.324-331. Available at: http://pubs.acs.org/doi/abs/10.1021/acs.jnatprod.5b00949 [Accessed 14 Oct. 2017].

⁶TURNER, C. and ELSOHLY, M. (1981). Biological Activity of Cannabichromene, its Homologs and Isomers. The Journal of Clinical Pharmacology, [online] 21(S1), pp.283S-291S. Available at: http://onlinelibrary.wiley.com/doi/10.1002/j.1552-4604.1981.tb02606.x/abstract;jsessionid=5438D2DDBA8A4160886BF4E402A440A3.f02t04.

⁷El-Alfy, A., Ivey, K., Robinson, K., Ahmed, S., Radwan, M., Slade, D., Khan, I., ElSohly, M. and Ross, S. (2010). Antidepressant-like effect of Δ9-tetrahydrocannabinol and other cannabinoids isolated from Cannabis sativa L. Pharmacology Biochemistry and Behavior, [online] 95(4), pp.434-442. Available at: http://www.sciencedirect.com/science/article/pii/S0091305710000730 [Accessed 14 Oct. 2017].

Some additional cannabinoids include:

  • THCA (Δ9-tetrahydrocannabinolic acid): A non-psychoactive chemical¹ within fresh, raw, undried cannabis. It has a variety of properties including being anti-inflammatory², neuroprotective³, and antiemetic⁴.
  • CBDA (Cannabidiolic acid): A non-psychoactive chemical found in the resin glands (trichomes) of raw cannabis plants⁵, and the acidic precursor of CBD. CBDA is thought to be an antioxidant⁶, as well as a painkiller⁷ and antimicrobial⁸.
  • CBGA (Cannabichromenenic acid): CBGA can be thought of as the stem cell cannabinoid⁹ because through varying types of biosynthesis, such as THC biosynthase or CBD biosynthase, CBGA can become THC / THCA, CBD / CBDA, CBC / CBCA, and CBG.¹⁰

 

Some less studied cannabinoids include CBL (Cannabicyclol), CBV (Cannabivarin), CBDVA (Cannabidivarinic acid), CBCVA (Cannabichromevarinic acid), CBGVA (Cannabigerovarinic acid), CBGM (Part of the Cannabigerol family), and CBE (Cannabielsoin), among others.

 


 

¹Starks, M. (1995). Marijuana chemistry. Berkeley, Calif: Ronin.

²Ruhaak, L., Felth, J., Karlsson, P., Rafter, J., Verpoorte, R. and Bohlin, L. (2011). Evaluation of the Cyclooxygenase Inhibiting Effects of Six Major Cannabinoids Isolated from Cannabis sativa. Biological & Pharmaceutical Bulletin, [online] 34(5), pp.774-778. Available at: https://www.jstage.jst.go.jp/article/bpb/34/5/34_5_774/_article [Accessed 20 Oct. 2017].

³Moldzio, R., Pacher, T., Krewenka, C., Kranner, B., Novak, J., Duvigneau, J. and Rausch, W. (2012). Effects of cannabinoids Δ(9)-tetrahydrocannabinol, Δ(9)-tetrahydrocannabinolic acid and cannabidiol in MPP+ affected murine mesencephalic cultures. Phytomedicine, [online] 19(8-9), pp.819-824. Available at: http://www.sciencedirect.com/science/article/pii/S0944711312001249?via%3Dihub [Accessed 20 Oct. 2017].

⁴Rock, E., Kopstick, R., Limebeer, C. and Parker, L. (2013). Tetrahydrocannabinolic acid reduces nausea-induced conditioned gaping in rats and vomiting inSuncus murinus. British Journal of Pharmacology, [online] 170(3), pp.641-648. Available at: http://onlinelibrary.wiley.com/doi/10.1111/bph.12316/abstract;jsessionid=F34850D2B90C65A4EA10511EF81EEDFC.f02t04 [Accessed 20 Oct. 2017].

⁵Butterfield, D. (2017). Cannabidiolic Acid (CBDA): The Raw Cannabinoid That Fights Inflammation. [online] HERB. Available at: https://herb.co/2017/05/20/cbda/ [Accessed 20 Oct. 2017].

⁶HAMPSON, A., GRIMALDI, M., LOLIC, M., WINK, D., ROSENTHAL, R. and AXELROD, J. (2006). Neuroprotective Antioxidants from Marijuanaa. Annals of the New York Academy of Sciences, [online] 899(1), pp.274-282. Available at: http://onlinelibrary.wiley.com/doi/10.1111/j.1749-6632.2000.tb06193.x/abstract [Accessed 20 Oct. 2017].

⁷Izzo, A., Borrelli, F., Capasso, R., Di Marzo, V. and Mechoulam, R. (2009). Non-psychotropic plant cannabinoids: new therapeutic opportunities from an ancient herb. Trends in Pharmacological Sciences, [online] 30(10), pp.515-527. Available at: http://www.stcm.ch/en/files/paper_izzo_tips_2009.pdf [Accessed 20 Oct. 2017].

⁸Leizer, C., Ribnicky, D., Poulev, A., Dushenkov, S. and Raskin, I. (2000). The Composition of Hemp Seed Oil and Its Potential as an Important Source of Nutrition. Journal of Nutraceuticals, Functional & Medical Foods. Available at: http://www.davoil.ro/documente/the-composition-of-seed-oil-and-its-potential-as-an-important-source-nutrition.pdf [Accessed 20 Oct. 2017].

⁹McGee, K. (2016). CBGa: The Cannabinoid Stem Cell | THCU Insider. [online] THCU Insider. Available at: http://insider.thcuniversity.org/cbga-the-cannabinoid-stem-cell/ [Accessed 20 Oct. 2017].

¹⁰Understanding Medical Cannabis. (2013). [ebook] Elemental Wellness. Available at: http://cannagramma.com/wp-content/uploads/2016/10/UnderstandingCannabis.pdf [Accessed 20 Oct. 2017].

Flavonoids are an important compound contributing color and pigmentation to plants. It is responsible for the colors of petals in flowers, as well as colors in many other plants.

Flavonoids that have been found in cannabis are called cannaflavins¹ ² and have been studied for their anti-inflammatory properties³.


¹Radwan, M., ElSohly, M., Slade, D., Ahmed, S., Wilson, L., El-Alfy, A., Khan, I. and Ross, S. (2008). Non-cannabinoid constituents from a high potency Cannabis sativa variety. Phytochemistry, [online] 69(14), pp.2627-2633. Available at: https://www.ncbi.nlm.nih.gov/pubmed/18774146?dopt=Abstract [Accessed 19 Oct. 2017].

²ElSohly, M. and Slade, D. (2005). Chemical constituents of marijuana: The complex mixture of natural cannabinoids. Life Sciences, [online] 78(5), pp.539-548. Available at: http://www.sciencedirect.com/science/article/pii/S002432050500891X?via%3Dihub [Accessed 19 Oct. 2017].

³Barrett, M., Gordon, D. and Evans, F. (1985). Isolation from cannabis sativa L. of cannflavin—a novel inhibitor of prostaglandin production. Biochemical Pharmacology, [online] 34(11), pp.2019-2024. Available at: http://www.sciencedirect.com/science/article/pii/0006295285903259?via%3Dihub [Accessed 19 Oct. 2017].

The most common routes of administration for medical cannabis are oral, topical, and inhalation.

Oral delivery includes all methods where the cannabis product is taken through the mouth. For example, indigestible oils, tinctures, and capsules.

Topical cannabis products are absorbed through the skin and can include salves, ointments, lotions, and sprays.

Inhalation involves smoking or vaporization and allows the gases from the lit cannabis product to enter the lungs for quicker relief.

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