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Terpenes

Terpenes are an incredibly diverse group of low molecular weight organic molecules that occur naturally in many medicinal plants, flowers, fruits, herbs, as well as some insects.  These compounds are responsible for the characteristic aroma/essence associated with these species (e.g. citrus fruits, lavender, hops, pine needles, cilantro). Terpenes are the largest group of plant chemicals and are ubiquitous in nature with some 15-20,000 distinct compounds fully characterized (Langenheim, J. H. J. Chem. Ecol. 1994, 20, 1223-1279). 

Over 200 terpenes have been identified in the cannabis plant (Rothschild, M.; Bergstrom, G.; Wangberg, S-A. Bot. J. Linn. Soc. 2005, 147, 387-397). These compounds are responsible not only for the distinct aroma and taste of various hemp strains, but are also believed to contribute to the different physiologic effects (energy, focus, creativity, relaxation, etc.) associated with each strain (McPartland, J. M.; Russo, E. B. J. Cannabis Therap. 2001, 1, 103-132).   The pharmacology of cannabis terpenes is still not well understood but continues to be studied as the wealth of anecdotal effects due to different terpene profiles continues to build (Nahtigal, I.; Blake, A.; Hand, A.; Florentinus-Mefailoski, A.; Hashemi, H.; Friedberg, J. J. Pain Management 2016, 9, 481-491).  

Some useful information relating to the most prominent terpenes found in cannabis (industrial hemp) is given below:

Bisabolol (Bis)

chemical structure of bisabolol terpene

Bisabolol is a sesquiterpenoid alcohol with a weak, sweet floral aroma and citrus and spice undertones.  It is the primary constituent of the essential oil from German chamomile.  Studies suggest that it possesses anti-inflammatory, anti-microbial, and anti-cancer properties (Kamatou, G.; Viljoen, A. J. Am. Oil Chem. Soc. 2010, 87, 1-7).  

Caryophyllene (Car)

chemical structure of caryophyllene terpene

Caryophyllene is a very common sesquiterpene found in cannabis, cloves, rosemary, and it contributes to the aroma of black pepper. Pharmacologically, it possesses anti-inflammatory activity (Basile, A. C.; Sertie, J. A.; Freitas, P. C. Zanini, A. C. J. Ethnopharmacol. 1988, 22, 101-109) and remarkably, is the first proven phytocannabinoid outside of the cannabis genus to be a selective full agonist at CB2 receptors (Gertsch, J.; Leonti, M.; Raduner, S.; Racz, I.; Chen, J. Z.; Xie, X. Q. Proc. Natl. Acad. Sci. USA 2008, 105, 9099-9104; Alberti, T.; Barbosa, W.; Vieira, J.; Raposo, N.; Dutra, R. Int. J. Mol. Sci. 2017, 18, 691).  

Eucalyptol (Euc)

chemical structure of eucalyptol terpene

Eucalyptol is a monoterpene ether commonly found in eucalyptus leaves, bay leaf, sage, rosemary, tea tree oil, and cannabis.  It has a penetrating mint aroma and a spicy, cooling taste. It has been used as a nasal decongestant and anti-cough agent and has been shown to have bronchodilator activity (Soares, M.; Damiani, C.; Moreira, C.; Stefanon, I.; Vassallo, D. Braz. J. Med. Biol. Res. 2005, 38, 453-461).

Geraniol (Ger)

chemical structure of geraniol terpene

Geraniol is a monoterpenoid alcohol that is found in significant quantities in rose oil and citronella oil and at lower levels in geraniums, bergamot and citrus fruits.  It has a rose-like aroma. Studies suggest that it possesses anti-inflammatory, anti-microbial, and anti-cancer properties (Kamatou, G.; Viljoen, A. J. Am. Oil Chem. Soc. 2010, 87, 1-7).  

Guaiol (Gua)

chemical structure of guaiol terpene

Guaiol is a sesquiterpene alcohol found in cypress pine, guaiacum shrubs, and cannabis.  It has a pine-like aroma with woody and rose undertones.  It has been shown to possess strong anxiolytic properties (Kamal, B. S.; Kamal, F.; Lantela, D. E. Front. Neurosci. 2018, 12, 1-14) and to effectively inhibit the proliferation of non-small cell lung carcinoma (NSCLC) cells in vitro (Yang, X.; Zhu, J.; Wu, J.; Huang, N.; Cui, Z.; Luo, Y.; Sun, F.; Pan, Q.; Li, Y.; Yang, Q. Cancer Biol. Ther. 2018, 19, 706-714).

Humulene (Hum)

chemical structure of humulene terpene

Humulene (aka alpha-caryophyllene) is a sesquiterpene found in hops, pine trees, orange trees, ginseng, ginger, sage, and cannabis. It has a woody, earthy, herbal aroma with spice undertones.  As such, it plays a significant role in the aroma of cannabis.  Studies suggest that it possesses anti-inflammatory and analgesic properties (Fernandes, E. F.; Passos, G. F.; Medeiros, R.; da Cunha, F.; Ferreira, J.; Campos, M.; Pianowski, L.; Calixto, J. Eur. J. Pharmacol. 2007, 569, 228-236).  

Limonene (Lim)

chemical structure of limonene terpene

Limonene is the second most widely distributed terpene in nature and is commonly found in lemons and other citrus fruits. Pharmacological effects associated with limonene include potent anxiolytic (anxiety-reducing) activity in mice (Pultrini Ade, M.; Galindo, L. A.; Costa, M. Life Sci. 2006, 78, 1720-1725), antidepressant activity in humans (Komori, T.; Fujiwara, R.; Tanida, M.; Nomura, J.; Yokoyama, M. M. Neuroimmunomodulation 1995, 2, 174-180), anti-stress effects in rat brain (Fukumoto, S.; Morishita, A.; Furutachi, K.; Terashima, T.; Nakayama, T.; Yokogoshi, H. Stress Health 2008, 24, 3-12) and potent radical scavenging effects (Choi, H. S.; Song, H. S.; Ukeda, H.; Sawamura, M. J. Agric. Food Chem. 2000, 48, 4156-4161).  

Linalool (Lin)

chemical structure of linalool terpene

Linalool, a monoterpenoid alcohol, is responsible for the well-known psychotropic anxiolytic properties of lavender.  It exudes a fresh, clean floral aroma with a citrus undertone.  Linalool has been shown to be an inhalation sedative in mice studies (Buchbauer, G.; Jirovetz, L.; Jager, W.; Dietrich, H.; Plank, C. Z. Naturforsch 1991, 46, 1067-1072) and has anesthetic properties similar to procaine and menthol (Ghelardini, C.; Galeotti, N.; Salvatore, G.; Mazzanti, G. Planta Med. 1999, 65, 700-703).  Additionally, linalool was shown to have anticonvulsant activity ( Elisabetsky, E.; Marschner, J.; Souza, D. O. Neurochem. Res. 1995, 20, 461-465)) and is thought to modulate glutamate and GABA neurotransmitter systems resulting in its anxiolytic, sedative, and anticonvulsant properties (Nunes, D. S.; Linck, V. M.; da Silva, A. L.; Figueiro, M.; Elisabetsky, E. “Psychopharmacology of Essential Oils. In: Handbook of Essential Oils.”  CRC Press 2010, 297-314).

Myrcene (Myr)

chemical structure of myrcene terpene

Myrcene is a monoterpene that occurs as a significant component of the essential oils of several plant species including hops, parsley, wild thyme, ylang-ylang, lemon grass, mango and cannabis.  Myrcene is pungently fragrant with notes of grape, peach, vanilla, balsamic vinegar and pepper with a woody undertone.   

Pharmacologically, myrcene has anti-inflammatory, analgesic and sedative properties (Lorenzetti, B. B.; Souza, G. E.; Sarti, S. J.; Santos, D.; Ferreira, S. H. J. Ethnopharmacol. 1991, 34, 43-48; Rao, V. S.; Menezes, A. M.; Viani, G. S. J. Pharm. Pharmacol. 1990, 42, 877-878; Bisset, N. G.; Wichtl, M. “Herbal Drugs and Phytopharmaceuticals” (2004) CRC Press)  

Nerolidol (Ner)

chemical structure of nerolidol terpene

Nerolidol is a sequiterpenoid alcohol that is typicall found in low levels in orange and other citrus peels, ginger, jasmine, lavender, lemon grass and cannabis sativa.  The compound’s aroma is woody and reminiscent of fresh bark.  It is known to have sedative properties (Binet, L.; Binet, P. Miocque, M.; Roux, M.; Bernier, A. Ann. Pharm. Fr. 1972, 30, 611-616) and anti-fungal activity (Langenheim, J. H. J. Chem. Ecol. 1994, 20, 1223-1279). 

Ocimene (Oci)

chemical structure of ocimene terpene

Ocimene is a monoterpene that is found in mango, mango ginger rhizome, basil, tarragon, marigolds, and cannabis.  It exudes an herbaceous aroma with fruity and woody undertones.  As a major component of essential oil derived from marigolds, it has been implicated in anticancer activity in in vitro and in vivo studies (Mahmoud, G. I. J. Med. Plants Res. 2013, 7, 561-572). 

Pinene (Pin)

chemical structure of pinene terpene

Pinene is the most widely encountered terpene in nature.  It appears prominently in conifers where it acts as an insect repellant.  Not surprisingly, it smells like fresh pine needles (think Christmas tree sap).  Pharmacological effects associated with pinene include broad spectrum antibiotic activity (Nissen, L.; Zatta, A.; Stefanini, I.; Grandi, S.; Sgorbati, B.; Biavati, B. Fitoterapia 2010, 81, 413-419), anti-inflammatory activity (Gil, M. L.; Jimenez, J.; Ocete, M. A.; Zarzuelo, A.; Cabo, M. M. Pharmazie 1989, 44, 284-287), and inhibition of acetylcholinesterase (memory aid) (Perry, N. S.; Houghton, P. J.; Theobald, A.; Jenner, P.; Perry, E. K. J. Pharm Pharmacol. 2000, 52, 895-902).   

Terpinolene (Ter)

chemical structure of terpinolene terpene

Terpinolene is a monoterpene that is found in apples, nutmeg, cumin, rosemary, tea tree oil, and cannabis.  It has a woody aroma with citrus and floral undertones.  It is one of the more elusive terpenes in cannabis, occurring at significant levels only in strains such as Jack Herer and Pineapple Kush.  It possesses broad spectrum antibacterial activity (Eftekhar, F.; Yousefzadi, M.; Azizian, D.; Sonboli, A.; Salehi, P. Z. Naturforsch. 2005, 821-825), has inhalation sedative properties in  mice (Ito, K.; Ito, M. J. Nat. Med. 2013, 67, 833-837) and has been shown to markedly reduce the expression of protein kinase B, an enzyme involved in a variety of human cancers (Okumura, N.; Yoshida, H.; Nishimura, Y.; Kitagishi, Y.; Matsuda, S. Oncol. Lett. 2012, 3, 321-324).

Valencene (Val)

chemical structure of Valencene terpene

Valencene is a sesquiterpene commonly found in Valencia oranges and common sedge.  It has a sweet, citrus scent and bitter citrus flavor.  It has been shown to to be a major contributor to the anti-allergic activity of common sedge (Cyperus rotundus) (Jin, J. H.; Lee, D. U.; Kim, Y. S.; Kim, H. P. Arch. Pharm. Res. 2011, 34, 223-228).

 FDA Disclaimer

**These statements have not been evaluated by the Food and Drug Administration. These products are not intended to diagnose, treat, cure, or prevent any disease.**

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