(-)-Caryophyllene oxide is a bicyclic sesquiterpene and a metabolite of β-caryophyllene that has been found in C. sativa and has anticancer properties. Unlike β-caryophyllene, (-)-caryophyllene oxide does not bind to the cannabinoid (CB) receptor CB2 (Ki = >20 μM). It induces calcium currents in HL-60 cells expressing CB2 receptors but also does so in CB2-deficient cells. (-)-Caryophyllene oxide is cytotoxic to HepG2, AGS, HeLa, SNU-1 and SNU-16 cells (IC50s = 3.95, 12.6, 13.55, 16.79, and 27.39 μM, respectively). It is the volatile component of C. sativa sensed by narcotic detection dogs. Formulations containing (-)-caryophyllene have been used as flavoring agents.

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