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547190

Sigma-Aldrich

Berbamine dihydrochloride

Synonym(s):

berbenine

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About This Item

Empirical Formula (Hill Notation):
C37H40N2O6 ·2HCl
CAS Number:
6078-17-7
Molecular Weight:
681.65
MDL number:
MFCD11982910
UNSPSC Code:
12352005
PubChem Substance ID:
24878760
NACRES:
NA.22

form

solid

optical activity

[α]20/D +116°, c = 1% in ethanol

mp

250-253 °C (lit.)

SMILES string

Cl.Cl.COc1cc2CCN(C)[C@H]3Cc4ccc(Oc5cc(C[C@H]6N(C)CCc7cc(OC)c(OC)c(Oc1cc23)c67)ccc5O)cc4

InChI

1S/C37H40N2O6.2ClH/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-31-18-23(8-11-30(31)40)17-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33;;/h6-11,18-21,28-29,40H,12-17H2,1-5H3;2*1H/t28-,29+;;/m0../s1

InChI key

USRXDYNDPPUBSG-KKXMJGKMSA-N

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Application

Reactant for:
  • Preparation of and anti-leukemia active berbamine derivatives

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Yun Liang et al.
Journal of Zhejiang University. Science. B, 12(7), 568-574 (2011-07-05)
The cytotoxic effect of berbamine on chronic myeloid leukemia (CML) cell line KU812 was evaluated, and the mechanisms of its action were explored. The effect of berbamine on the KU812 cell growth was determined by methyl thiazolyl tetrazolium (MTT) assay.
Cai-Mei Zhang et al.
Journal of cardiovascular pharmacology, 58(1), 40-48 (2011-07-15)
Berbamine (BM), a natural compound derived from Berberis vulgaris L, has been reported to inhibit cardiac contractile function at higher concentrations. Here, we report that BM had concentration-dependent biphasic effects on myocardial contraction in Langendorff-perfused rat hearts, that is, at
Rong Liu et al.
Journal of pharmaceutical sciences, 99(7), 3266-3275 (2010-01-30)
Multidrug resistance (MDR) mediated by the overexpression of the drug efflux protein P-glycoprotein is one of the major obstacles to successful cancer chemotherapy. The development of safe and effective MDR-reversing agents is an important approach to addressing this problem clinically.
Yun Liang et al.
Acta pharmacologica Sinica, 30(12), 1659-1665 (2009-12-05)
We sought to investigate the effect of berbamine on the growth of human multiple myeloma cell line KM3 and elucidate the mechanism of its action. MTT assay was used to determine the inhibitory effect of berbamine alone or combined with
Yanli Cui et al.
European journal of medicinal chemistry, 54, 867-872 (2012-05-29)
A series of berbamine glycosides was designed, synthesized and evaluated as a new class of antitumor agents. An efficient glycosylation route was developed for berbamide derivatives. The newly synthesized glycosides were evaluated for their cytotoxic activity in vitro against a
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