BERBAMINE DIHYDROCHLORIDE CAS 6078-17-7
BERBAMINE DIHYDROCHLORIDE Basic information
| Product Name: | BERBAMINE DIHYDROCHLORIDE |
| Synonyms: | BERBENINE;BERBAMINE DIHYDROCHLORIDE;BERBAMINE HCL;BERBAMINE 2HCL;(4aS,16aR)-3,4,4a,5,16a,17,18,19-Octahydro-21,22,26-trimethoxy-4,17-dimethyl-16H-1,24:6,9-dietheno-11,15-metheno-2H-pyrido[2',3':17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolin-12-ol hydrochloride;6,6',7-Trimethoxy-2,2'-dimethylberbaman-12-ol dihydrochloride;Berbaman-12-ol,6,6',7-trimethoxy-2,2'-dimethyl-, dihydrochloride (9CI);Berbamine dihydrochloride, >95% |
| CAS: | 6078-17-7 |
| MF: | C37H42Cl2N2O5 |
| MW: | 665.65 |
| EINECS: | 200-001-8 |
| Product Categories: | reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical |
| Mol File: | 6078-17-7.mol |
BERBAMINE DIHYDROCHLORIDE Chemical Properties
| Melting point | 250-253 °C(lit.) |
| storage temp. | under inert gas (nitrogen or Argon) at 2-8°C |
| solubility | ≥68 mg/mL in DMSO; ≥10.68 mg/mL in H2O; ≥4.57 mg/mL in EtOH |
| form | solid |
| color | White to off-white |
| Optical Rotation | [α]20/D +116°, c = 1% in ethanol |
| InChIKey | SFPGJACKHKXGBH-BISAGJBCNA-N |
| SMILES | C12[C@@H]3N(CCC=1C=C(OC)C(OC)=C2OC1C(OC)=CC2CCN(C)[C@@H](CC4C=CC(=CC=4)OC4=C(O)C=CC(=C4)C3)C=2C=1)C.Cl |&1:1,25,r| |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-36/37/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Chemical Properties | White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the rhizome of Coptis chinensis and the root of Berberis vulgaris (Three Needles). |
| Uses | Reactant for:
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| Uses | (+)-Berbamine Dihydrochloride exerts anti-inflammatory effects through inhibition of NF-κB and MAPK signalling pathways. |
| Biological Activity | extracted from berberidis;store the product in sealed, cool and dry condition |
| Synthesis | 478-61-5 6078-17-7 In a 250 mL three-necked flask, 60 mL of deionized water was added followed by 10 g of hydrated saponinamine. Under stirring conditions, the pH of the reaction system was adjusted to 1.5-3.5 by slow dropwise addition of 6 M hydrochloric acid solution. the reaction mixture was stirred continuously for 30 minutes. Appropriate amount of activated carbon was added and stirring was continued for 10 min before the activated carbon was removed by thermal filtration. The filtrate was concentrated to 1/3 of the original volume in a rotary evaporator. appropriate amount of isopropanol was added to the concentrate and cooled to 0-5 °C in an ice water bath to precipitate crystals. The crystalline solid was collected by filtration and washed with a small amount of cold isopropanol. The resulting solid was pre-dried in an oven at 30°C for 2 days and subsequently transferred to a glass desiccator fitted with silica gel desiccant and further dried at room temperature. Finally, the product was placed in a vacuum oven and dried under vacuum at 20 °C and 0.08 MPa for 6 h. 8.3 g of white to light yellow crystalline powder was obtained. Product identification: (1) About 10 mg of the product was dissolved in 5 mL of water and divided into two test tubes. Add 1 drop of bismuth potassium iodide solution to the first test tube and an orange-red precipitate was observed; add 1 drop of potassium iodide solution to the second test tube and a brown precipitate was observed. (2) About 10 mg of the product was dissolved in 5 mL of water, and 2 drops of ferric chloride solution and 1 drop of potassium ferricyanide test solution were added sequentially, and the solution appeared blue. |
| in vivo | Berbamine (BBM) is a natural bisbenzylisoquinoline product isolated from traditional Chinese herbal medicine Berberis amurensis and has been used to treat inflammatory and other diseases.The anti-tumor effects of Berbamine are determined on a xenograft animal model. Two liver cancer cell lines, Huh7 (epithelial) and SK-Hep-1 (mesenchymal-like), are inoculated into NOD/SCID mice by subcutaneous injection. The oral Berbamine treatment greatly suppresses the growth of Huh7 xenografted tumors over the time and leads to a tumor reduction by 70% based on the tumor weight. The growth of SK-Hep-1 cells in NOD/SCID mice is less sensitive to Berbamine than that of Huh7. There is a significant suppression of the growth of the SK-Hep-1 xenograft with more than 50% reduction of the tumor weight[2]. |
| target | cAMP | Calcium Channel |
| IC 50 | NF-κB; Autophagy |
| References | [1] Patent: CN103012421, 2016, B. Location in patent: Paragraph 0071; 0072 |
BERBAMINE DIHYDROCHLORIDE Preparation Products And Raw materials
| Raw materials | BERBAMINE-->Water-->Hydrochloric acid |
