A 13-methyl-substituted berberine
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13-Methylberberine (chloride)

Item No. 21154

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,6-dihydro-9,10-dimethoxy-13-methyl-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, monochloride
CAS Number
54260-72-9
Synonyms
  • 13-MB
Molecular Formula
C21H20NO4 • Cl
Formula Weight
385.8
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Water: 1 mg/ml
λmax
232, 266, 342, 423 nm
SMILES
COC1=CC=C2C(C)=C3[N+](CCC4=C3C=C5C(OCO5)=C4)=CC2=C1OC.[Cl-]
InChi Code
InChI=1S/C21H20NO4.ClH/c1-12-14-4-5-17(23-2)21(24-3)16(14)10-22-7-6-13-8-18-19(26-11-25-18)9-15(13)20(12)22;/h4-5,8-10H,6-7,11H2,1-3H3;1H/q+1;/p-1
InChi Key
MLEFNGNLISNJEQ-UHFFFAOYSA-M
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    13-Methylberberine (13-MB) (chloride) is a 13-methyl-substituted derivative of berberine (Item No. 10006427). Berberine is a widely distributed berberidaceaen alkaloid found in plant tissues that has antibacterial, anti-inflammatory, antitumor, anti-obesity, and hypercholesterolemic activity.1,2 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.3,4,5 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.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chow, Y.-L., Sogame, M., and Sato, F. 13-Methylberberine, a berberine analogue with stronger anti-adipogenic effects on mouse 3T3-L1 cells. Sci. Rep. 6, 38129 (2016).

    2. Kong, W., Wei, J., Abidi, P., et al. Berberine is a novel cholesterol-lowering drug working through a unique mechanism distinct from statins. Nat. Med. 10(12), 1344-1351 (2004).

    3. Iwasa, K., Kamigauchi, M., Ueki, M., et al. Antibacterial activity and structure-activity relationships of berberine analogs. Eur. J. Med. Chem. 31(6), 469-478 (1996).

    4. Iwasa, K., Moriyasu, M., Yamori, T., et al. In vitro cytotoxicity of the protoberberine-type alkaloids. J. Nat. Prod. 64(7), 896-898 (2001).

    5. Lee, D.U., Kang, Y.J., Park, M.K., et al. Effects of 13-alkyl-substituted berberine alkaloids on the expression of COX-II, TNF-α, iNOS, and IL-12 production in LPS-stimulated macrophages. Life Sci. 73(11), 1401-1412 (2003).