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Caryophylleen

β-Caryophyllene has the distinction of being the first known “dietary cannabinoid,” a common component of food that has GRAS (Generally Recognized as Safe) status and is approved by the FDA for food use. 

β-Caryophyllene is the primary sesquiterpene contributing to the spiciness of black pepper; it is also a major constituent of cloves, hops, rosemary, copaiba, and cannabis. It was one of the first cannabis-derived compounds other than THC, CBD, and CBN shown to bind directly to endocannabinoid receptors (Gertsch, 2008). In fact, it was one of the first cannabis-derived compounds with a fundamentally different structure from the classical cannabinoids that interacts with the endocannabinoid system in humans. β-Caryophyllene is known to selectively bind to the CB2 receptor; therefore, it is sometimes also classed as an atypical cannabinoid (Gertsch et al., 2010). As described elsewhere in this chapter, CB1 is responsible for the psychoactive effects associated with certain cannabinoids such as THC. However, CB2, particularly in peripheral tissues in the body, is a therapeutic target for treatment of inflammation, pain, atherosclerosis, and osteoporosis (Gertsch, 2008; Gertsch et al., 2008). 

β-Caryophyllene has now been shown to be directly beneficial for colitis (Bento et al., 2011), osteoarthritis (Rufino et al., 2015), diabetes (Basha and Sankaranarayanan, 2014), cerebral ischemia (Chang et al., 2013), anxiety and depression (Bahi et al., 2014), liver fibrosis (Calleja et al., 2013; Mahmoud et al., 2014), and Alzheimer-like disease types (Cheng et al., 2014). In cancer studies, β-caryophyllene demonstrated synergy with the chemotherapy drug Paclitaxel on human tumor cell lines, and alone it stimulates apoptosis and suppresses tumor growth (Legault and Pichette, 2007). In a Caenorhabditis elegans model, β-caryophyllene modulated stress-related genes and extended the lifespan of the organism (Pant et al., 2014). Importantly, it has been shown to be orally bioavailable; therefore, it would provide an important medicinal benefit to oral cannabis preparations.
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