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 activity

[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

MSDS

• Language:English Provider:SigmaAldrich

BERBAMINE DIHYDROCHLORIDE Usage And Synthesis

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:

• Preparation of and anti-leukemia active berbamine derivatives

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

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

target

cAMP | Calcium Channel

IC 50

NF-κB; Autophagy

References

[1] Patent: CN103012421, 2016, B. Location in patent: Paragraph 0071; 0072

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