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| | Berberine hydrochloride Basic information |
| | Berberine hydrochloride Chemical Properties |
| Melting point | 204-206 °C (dec.) | | storage temp. | Inert atmosphere,2-8°C | | solubility | methanol: soluble | | form | Yellow powder | | Colour Index | 75160 | | color | Yellow powder | | Water Solubility | SOLUBLE IN COLD WATER | | BRN | 3836585 | | Stability: | Hygroscopic | | InChI | InChI=1S/C20H18NO4.ClH/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;/p-1 | | InChIKey | VKJGBAJNNALVAV-UHFFFAOYSA-M | | SMILES | C12C=C3C(C(OC)=C(OC)C=C3)=C[N+]=1CCC1=CC3=C(OCO3)C=C21.[Cl-] | | CAS DataBase Reference | 633-65-8 | | EPA Substance Registry System | Berberine chloride (633-65-8) |
| Hazard Codes | Xn | | Risk Statements | 20/21/22-36/37/38 | | Safety Statements | 24/25-36-26 | | RIDADR | 1544 | | WGK Germany | 2 | | RTECS | DR9866400 | | F | 3-10 | | TSCA | Yes | | HazardClass | 6.1(b) | | PackingGroup | III | | HS Code | 29349990 | | Toxicity | LD50 orl-rat: >15 g/kg KSRNAM 8,654,74 |
| | Berberine hydrochloride Usage And Synthesis |
| Chemical Properties | yellow crystalline powder | | Uses | antiarrhythmic, alpha2 agonist, anticonvulsant, antiinflammatory, antibacterial, antifungal, antitrypanosomal, antineoplastic, immunostimulant | | Uses | An isoqinoline alkaloid shown to have a chemopreventive property against colon tumor formation by inhibiting the enzyme cyclooxygenase-2 (cox-2) which is abundantly expressed in colon cancer cells. Al
so inhibits Activator Protein 1 (AP-1), a transcription factor that plays a critical role in inflammation and carcinogenesis. Treatment with berberine potentially results in the reduced accumulation o
f chemotherapeutic drugs. | | Uses | An ingredient in some commercial eyewash products. | | Definition | ChEBI: Berberine chloride (TN) is an organic molecular entity. | | General Description | A highly potent and selective oxysterol EBI2 (GPR183) agonist (Kd) = 450 pM in a saturation binding assay, and EC50 = 140 pM over EC50 = 2.1 nM for its enantiomer, 7β,25-OHC, in a GTP-γS binding assay). Dose-dependently suppresses forskolin-induced cAMP accumulation in an EBI2-expressing SK-N-MC/CRE-β-galactosidase cell line (IC50 = 2 nM), but not in control cells. Stimulates migration of LPS-activated spleen B-cells and anti-CD3/CD28-activated CD4+ T-cells in a dose-dependent manner. In addition, pharmacological inhibition of its biosynthesis in vivo by Clotrimazole, a CYP7B1inhibitor, promotes the migration of adoptively transferred pre-activated B cells to the T/B boundary, mimicking the phenotype of pre-activated B cells in EBI2-deficient mice. | | Biochem/physiol Actions | An alkaloid with weak antibiotic properties. Substrate for MDR efflux pumps. Antimicrobial activities of berberine is potentiated by the MDR inhibitor 5′-methoxyhydnocarpin (5′-MHC). Berberine upregulates the expression of Pgp in hepatoma cells. Treatment with berberine potentially results in the reduced accumulation of chemotherapeutic drugs. | | Safety Profile | Poison by intraperitoneal route.Slightly toxic by ingestion. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx andCl-. | | Purification Methods | Berberine chloride crystallises from water to give the dihydrate. The anhydrous salt may be obtained by recrystallisation from EtOH/Et2O, wash the crystals with Et2O and dry them in a vacuum. The iodide has m 250o(dec) (from EtOH). [Perkin J Chem Soc 113 503 1918, Kametani et al. J Chem Soc(C) 2036 1969, Beilstein 27 I 515, 27 II 567.] |
| | Berberine hydrochloride Preparation Products And Raw materials |
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