beta-Caryophyllene

beta-Caryophyllene (Cay-21572) is a sesquiterpene that has been found in plants, including C. sativa, C. indica, and hemp, and has diverse biological activities, including lipid metabolic, antioxidant, anti-neuroinflammatory, anti-proliferative, and antinociceptive properties. It is an agonist of the cannabinoid (CB) receptor CB2 (Ki = 155 nM) that inhibits cAMP production induced by forskolin in CHO-K1 cells expressing CB2 receptors (EC50 = 38 nM). beta-Caryophyllene is also an agonist of peroxisome proliferator-activated receptor alpha (PPARalpha, EC50 = 9.58 µM in a reporter assay). beta-Caryophyllene (1 and 2.5 µM) reduces the production of reactive oxygen species (ROS) in and protects against cytotoxicity of SH-SY5Y cells induced by 1-methyl-4-pheylpyridinium (MPP+). It also decreases the beta-amyloid burden in the hippocampus and cerebral cortex and improves memory in an APP/PS1 transgenic mouse model of Alzheimer's disease, decreasing the latency to find the platform in the Morris water maze during training and increasing the time spent in the target quadrant during testing when administered at a dose of 48 mg/kg per day. beta-Caryophyllene (50 mg/kg) increases the number of entries into and the time spent in the open arms of the elevated plus maze and the time spent immobile in the forced swim test, indicating anxiolytic-like and antidepressant-like activity, effects that can be blocked by the CB2 receptor antagonist AM630 (Cay-10006974).Formal Name: (1R,4E,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene. CAS Number: 87-44-5. Synonyms: (-)-beta-Caryophyllene, (-)-trans-Caryophyllene, NSC 11906. Molecular Formula: C15H24. Formula Weight: 204.4. Purity: >95%. Formulation: (Request formulation change), A neat oil. SMILES: CC1(C)C[C@@]2([H])[C@@]1([H])CC/C(C)=C/CCC2=C. InChi Code: InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1. InChi Key: NPNUFJAVOOONJE-GFUGXAQUSA-N. Origin: Synthetic.