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What Are Terpenes?

What Are Terpenes?

July 17, 2019

Terpenes are volatile hydrocarbon molecules that are ubiquitous in the plant world. They are commonly used for culinary purposes and aromatherapy. Cannabinoids are not the only chemicals in hemp; terpenes are also abundant. They confer important benefits and may play a critical role in the entourage effect [1].

At least 150 distinct terpenes have been identified in hemp [2]. Terpenes give hemp its aroma and flavor. They secrete from the same glands that produce cannabinoids and serve protective and regulatory functions [3]. Hemp terpenes generally align to one of two chemical structures:

  • Monoterpene: C10H16 (two isoprene units)
  • Sesquiterpene: C15H24 (three isoprene units)

 

Top Terpenes

Here are some of the top terpenes in full spectrum hemp products:

 

β-caryophyllene

β-caryophyllene is a sesquiterpene that may have evolved in hemp to protect against insect herbivores. It is commonly found in black pepper [1]. 

This is the only known terpene to act on the endocannabinoid system directly; it is an agonist of the CB2 receptor [2,4]. For this reason, researchers in 2008 gave it the moniker, “dietary cannabinoid” [4]. In mice, β-caryophyllene was shown to act as an effective local anesthetic [5].

β-myrcene

β-myrcene is a monoterpene most notable in hop and used in brewing [1]. This terpene is associated with sedative effects as demonstrated in mice [6]. It may also have anti-inflammatory and analgesic effects [1].

Linalool

Linalool is also a monoterpene; it is famous for its presence in lavender [1]. Linalool has demonstrated anxiolytic effects in several murine studies [7,8]. It is thought to be an anticonvulsant, and plant species with linalool are part of the traditional medicine in the Brazilian Amazon [9]. Lavender oil, which is high in linalool, shows potential as an adjunctive therapy for mild depression [10]. 

Limonene

D-limonene (or limonene) is a monoterpene that effectively repels insects; in fact, it is used in commercial insecticides [11]. Limonene is commonly found in the peels of lemons and citrus fruit [1].

Potential clinical applications of limonene include dissolving cholesterol-based gallstones and relieving heartburn. This terpene has also been investigated for anti-cancer properties [12].

α-pinene

α-pinene is another monoterpene with a unique aroma and distinct therapeutic properties. Not surprisingly, it is predominant in pine needles [1].

α-pinene has been found to possess significant antibacterial properties; in one study, it matched the effectiveness of an antibiotic against MRSA and other resistant bacterial infections [13]. This terpene also appears to be a mild bronchodilator in humans [14], and may even boost short-term memory via inhibition of acetylcholinesterase [15].

 

This is just a snapshot of the many terpenes present in full spectrum CBD. The specific ways that these terpenes synergize with cannabinoids is unclear, but the individual benefits are evident. Like cannabinoids, terpenes are part of nature’s great reservoir of healing compounds.

  1. Russo E.B. (2011). Taming THC: Potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. British Journal of Pharmacology,163(7), 1344-64. doi:10.1111/j.1476-5381.2011.01238.x
  2. Booth, J. K., & Bohlmann, J. (2019). Terpenes in Cannabis sativa – From plant genome to humans. Plant Science,284, 67-72. doi:10.1016/j.plantsci.2019.03.022
  3. Lange, B. M., & Turner, G. W. (2012). Terpenoid biosynthesis in trichomes-current status and future opportunities. Plant Biotechnology Journal,11(1), 2-22. doi:10.1111/j.1467-7652.2012.00737.x
  4. Gertsch, J., et al. (2008). Beta-caryophyllene is a dietary cannabinoid. Proceedings of the National Academy of Sciences,105(26), 9099-9104. doi:10.1073/pnas.0803601105
  5. Ghelardini, C., et al. (2001). Local anaesthetic activity of β-caryophyllene. Il Farmaco,56(5-7), 387-389. doi:10.1016/s0014-827x(01)01092-8
  6. Vale, T. G., et al. (2002). Central effects of citral, myrcene and limonene, constituents of essential oil chemotypes from Lippia alba (Mill.) N.E. Brown. Phytomedicine,9(8), 709-714. doi:10.1078/094471102321621304
  7. Linck, V. M., et al. (2010). Effects of inhaled Linalool in anxiety, social interaction and aggressive behavior in mice. Phytomedicine, 17(8), 679–683. https://doi.org/https://doi.org/10.1016/j.phymed.2009.10.002
  8. Souto-Maior, F. N., et al. (2011). Anxiolytic-like effects of inhaled linalool oxide in experimental mouse anxiety models. Pharmacology Biochemistry and Behavior, 100(2), 259–263. https://doi.org/https://doi.org/10.1016/j.pbb.2011.08.029
  9. Elisabetsky, E., Marschner, J., & Souza, D. O. (1995). Effects of linalool on glutamatergic system in the rat cerebral cortex. Neurochemical Research,20(4), 461-465. doi:10.1007/bf00973103
  10. Akhondzadeh, S., et al. (2003). Comparison of Lavandula angustifolia Mill. tincture and imipramine in the treatment of mild to moderate depression: A double-blind, randomized trial. Progress in Neuro-Psychopharmacology and Biological Psychiatry,27(1), 123-127. doi:10.1016/s0278-5846(02)00342-1
  11. Showler, A. T., Harlien, J. L., & Léon, A. A. (2019). Effects of Laboratory Grade Limonene and a Commercial Limonene-Based Insecticide on Haematobia irritans irritans (Muscidae: Diptera): Deterrence, Mortality, and Reproduction. Journal of Medical Entomology. doi:10.1093/jme/tjz020
  12. Sun, J. (2007). D-Limonene: Safety and clinical applications. Alternative Medicine Review, 12(3), 259-264.
  13. Köse, E. O., et al. (2010). Chemical composition, antimicrobial and antioxidant activities of the essential oils of Sideritis erythrantha Boiss. and Heldr. (var. erythrantha and var. cedretorum P.H. Davis) endemic in Turkey. Food and Chemical Toxicology,48(10), 2960-2965. doi:10.1016/j.fct.2010.07.033
  14. Falk, A. A., et al. (1990). Uptake, distribution and elimination of alpha-pinene in man after exposure by inhalation. Scandinavian Journal of Work, Environment & Health,16(5), 372-378. doi:10.5271/sjweh.1771
  15. Miyazawa, M., & Yamafuji, C. (2005). Inhibition of acetylcholinesterase activity by bicyclic monoterpenoids. Journal of Agricultural and Food Chemistry,53(5), 1765-1768. doi:10.1021/jf040019b



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