Crebanine

Crebanine is an aporphine alkaloid that has been found in Stephania venosa and has diverse biological activities. It is an antagonist of alpha7 nicotinic acetylcholine receptors (nAChRs, IC50 = 19.1 µM) and inhibits sodium currents (INa) in isolated guinea pig ventricular myocytes (IC50 = 283 µM). Crebanine is active against the Gram-positive bacteria M. lysodeikticus, B. cereus, B. megaterium, B. subtilis, and S. aureus (MICs = 0.312, 0.213, 0.312, 0.312, and 0.312 g/L, respectively). It inhibits the LPS-induced production of TNF-alpha, IL-6, nitric oxide (NO), and prostaglandin E2 (PGE2, Cay-14010) in RAW 264.7 macrophages when used at a concentration of 29.5 µM. Crebanine inhibits the proliferation of A549 lung, MDA-MB-231 and MCF-7 breast, and SKOV3 and Caov-3 ovarian cells and reduces TNF-alpha induced invasion and migration of A549 cells in a concentration-dependent manner. It prevents scopolamine-induced memory deficits in the Morris water maze in mice when administered at a dose of 25 mg/kg.Formal Name: (7R)-6,7,7a,8-tetrahydro-9,10-dimethoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline. CAS Number: 25127-29-1. Synonyms: (-)-Crebanine. Molecular Formula: C20H21NO4. Formula Weight: 339.4. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMF: 12 mg/ml, DMSO: 10 mg/ml, Ethanol: Slightly soluble. lambdamax: 217, 280 nm. SMILES: CN1[C@@]2([H])C3=C(CC1)C=C(OCO4)C4=C3C5=CC=C(OC)C(OC)=C5C2. InChi Code: InChI=1S/C20H21NO4/c1-21-7-6-11-8-16-20(25-10-24-16)18-12-4-5-15(22-2)19(23-3)13(12)9-14(21)17(11)18/h4-5,8,14H,6-7,9-10H2,1-3H3/t14-/m1/s1. InChi Key: UVDQDNQWGQFIAO-CQSZACIVSA-N. Origin: Plant/Stephania yunnanensis.