ChemicalBook > CAS DataBase List > 5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium

5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium

Product Name
5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium
CAS No.
54260-72-9
Chemical Name
5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium
Synonyms
13-Methylberberine;13-Methylberberinium Chlorid;13-Methylberberine (chloride);13-Methylberberine chloride, 10 mM in DMSO;13-methylberberine/13-Methylberberine chloride;2,3-(Methylenedioxy)-9,10-dimethoxy-13-methyl-5H,6H-dibenzo[a,g]quinolizin-7-ium;9,10-Dimethoxy-13-methyl-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium;9,10-Dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride;inhibit,Inhibitor,13 Methylberberine chloride,13Methylberberine chloride,Interleukin Related,13-Methylberberinium
CBNumber
CB82266822
Molecular Formula
C21H20ClNO4
Formula Weight
385.8408
MOL File
54260-72-9.mol
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5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium Property

Melting point:
198-200 °C
storage temp. 
Store at -20°C
solubility 
Water: 1 mg/ml
form 
A crystalline solid
color 
Light yellow to yellow
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical
Product number
21154
Product name
13-Methylberberine (chloride)
Purity
≥98%
Packaging
1mg
Price
$54
Updated
2024/03/01
Cayman Chemical
Product number
21154
Product name
13-Methylberberine (chloride)
Purity
≥98%
Packaging
5mg
Price
$231
Updated
2024/03/01
Cayman Chemical
Product number
21154
Product name
13-Methylberberine (chloride)
Purity
≥98%
Packaging
10mg
Price
$410
Updated
2024/03/01
AK Scientific
Product number
0436CB
Product name
5,6-Dihydro-9,10-dimethoxy-13-methylbenzo(g)-1,3-benzodioxolo(5,6-a)quinoliziniumchloride
Packaging
5mg
Price
$355
Updated
2021/12/16
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5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium Chemical Properties,Usage,Production

Description

13-Methylberberine (13-MB) (chloride) is a 13-methyl-substituted derivative of berberine . Berberine is a widely distributed berberidaceaen alkaloid found in plant tissues that has antibacterial, anti-inflammatory, antitumor, anti-obesity, and hypercholesterolemic activity. 13-MB has improved antibacterial activity against S. aureus (MIC = 125 μg/ml) and improved antitumor activity with a mean GI50 value of 11.7 μM, as compared to berberine. 13-MB also induces down-regulation of adipocyte differentiation transcription factors, reduces de novo lipid synthesis, and accumulates in murine 3T3-L1 adipocytes at higher levels than berberine, suggesting improved anti-obesity activity.

Uses

13-Methylberberinium Chloride can be used to treat and prevent immunoinflammatory dermal disorders. It can also be used in synthesis to result in derivatives that can be used to treat nerve diseases and anti-infective agents.

References

[1] YIT-LAI CHOW F S Mami Sogame. 13-Methylberberine, a berberine analogue with stronger anti-adipogenic effects on mouse 3T3-L1 cells[J]. Scientific Reports, 2016, 6 1. DOI: 10.1038/srep38129
[2] WEIJIA KONG. Berberine is a novel cholesterol-lowering drug working through a unique mechanism distinct from statins[J]. Nature Medicine, 2004, 10 12: 1344-1351. DOI: 10.1038/nm1135
[3] K IWASA . Antibacterial activity and structure-activity relationships of berberine analogs[J]. European Journal of Medicinal Chemistry, 1996, 31 6: Pages 469-478. DOI: 10.1016/0223-5234(96)85167-1
[4] KINUKO IWASA. In Vitro Cytotoxicity of the Protoberberine-Type Alkaloids[J]. Journal of Natural Products , 2001, 64 7: 896-898. DOI: 10.1021/np000554f
[5] DONG-UNG LEE . Effects of 13-alkyl-substituted berberine alkaloids on the expression of COX-II, TNF-α, iNOS, and IL-12 production in LPS-stimulated macrophages[J]. Life sciences, 2003, 73 11: Pages 1401-1412. DOI: 10.1016/s0024-3205(03)00435-1

5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium Preparation Products And Raw materials

Raw materials

Preparation Products

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54260-72-9, 5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinoliziniumRelated Search:

Cevadine veratramine ISOHEPTANE COPTISINE L-Hyoscyamine Groenlandicine 2-[2-(Methylamino)benzoyl]-3,4-dihydro-β-carboline-1(2H)-one Xanthiazone Worenine daurisoline Coptisine chloride Daurinoline menisdaurin VERATRIDINE epiberberine Tetrahydroepiberberine, Sinactine Xanthiside Tannic acid berberine

  • 13-Methylberberine
  • 2,3-(Methylenedioxy)-9,10-dimethoxy-13-methyl-5H,6H-dibenzo[a,g]quinolizin-7-ium
  • 5,6-Dihydro-2,3-(methylenedioxy)-9,10-dimethoxy-13-methyldibenzo[a,g]quinolizinium
  • 9,10-Dimethoxy-13-methyl-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
  • 13-Methylberberine (chloride)
  • 13-Methylberberinium Chlorid
  • 13-methylberberine/13-Methylberberine chloride
  • inhibit,Inhibitor,13 Methylberberine chloride,13Methylberberine chloride,Interleukin Related,13-Methylberberinium
  • 9,10-Dimethoxy-13-methyl-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
  • 13-Methylberberine chloride, 10 mM in DMSO
  • 54260-72-9