(+)-Kavain

(+)-Kavain is a kavalactone and the major constituent of the pepper plant kava (P. methysticum) and has diverse biological activities. It is a positive allosteric modulator of alpha4beta2delta subunit-containing GABAA receptors with EC50 values of 25 and 59 µM in the presence and absence of 300 µM (+)-kavain, respectively, in Xenopus oocytes expressing human receptors. (+)-Kavain reduces growth of WPMY-1 prostate cancer cells (IC50 = 5.2 µg/ml). It reduces LPS-induced TNF-alpha production in primary murine macrophages in a concentration-dependent manner. In vivo, (+)-kavain (1 mg/animal) reduces hind paw swelling and TNF-alpha production in wild-type, but not Erk-/-, mice in a mouse model of collagen-induced arthritis. (+)-Kavain also reduces acetic acid-induced abdominal constrictions in mice (ED50= 15.71 mg/kg).Formal Name: (6R)-5,6-dihydro-4-methoxy-6-[(1E)-2-phenylethenyl]-2H-pyran-2-one. CAS Number: 500-64-1. Synonyms: Kawain, NSC 112162. Molecular Formula: C14H14O3. Formula Weight: 230.3. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 25 mg/ml, DMSO: 25 mg/ml, Ethanol: 5 mg/ml. lambdamax: 210, 245 nm. SMILES: O=C1O[C@@H](/C=C/C2=CC=CC=C2)CC(OC)=C1. InChi Code: InChI=1S/C14H14O3/c1-16-13-9-12(17-14(15)10-13)8-7-11-5-3-2-4-6-11/h2-8,10,12H,9H2,1H3/b8-7+/t12-/m0/s1. InChi Key: XEAQIWGXBXCYFX-GUOLPTJISA-N. Origin: Synthetic.