Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-

The Berberine, with the CAS registry number 2086-83-1, is also known as 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium. Its EINECS number is 211-195-9. This chemical's molecular formula is C₂₀H₁₈NO₄ and molecular weight is 336.37. What's more, its systematic name is 9,10-Dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium. Its classification code is Mutation data. This chemical is used in histology for staining heparin in mast cells because of a strong yellow fluorescence. As a traditional medicine or dietary supplement, it has showed some activity against fungal infections, Candida albicans, yeast, parasites and bacterial/viral infections. Berberine is considered as an ineffective antibiotic and is a component of some eye drop formulations.

Physical properties of Berberine are: (1)ACD/LogP: 0.053; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.05; (4)ACD/LogD (pH 7.4): 0.05; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 25.46; (8)ACD/KOC (pH 7.4): 25.46; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 40.8 Å².

Preparation: this chemical can be prepared by C₂₁H₁₉NO₆. This reaction will need reagent sodium cyanoborohydride and solvent methanol. The yield is about 96%.

Uses of Berberine: it can be used to produce 9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline by heating. It will need reagents In, aq. NH₄Cl and solvent ethanol with the reaction time of 10 hours. The yield is about 83%.

You can still convert the following datas into molecular structure:
(1)SMILES: O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5
(2)Std. InChI: InChI=1S/C20H18NO4/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/q+1
(3)Std. InChIKey: YBHILYKTIRIUTE-UHFFFAOYSA-N

The toxicity data is as follows: