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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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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
Xiao-Xia Cheng et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 72(5), 922-928 (2009-02-03)
Berbamine, a naturally occurring isoquinoline alkaloid extracted from Berberis sp., is the active constituent of some Chinese herbal medicines and exhibits a variety of pharmacological activities. The effects of berbamine on the structure of bovine serum albumin (BSA) were investigated
Shan Wang et al.
Molecular cancer, 8, 81-81 (2009-10-03)
Breast cancer is the second leading cause of cancer related deaths among females worldwide. Berbamine (BER), a kind of bis-benzylisoquinoline alkaloid, has been used to treat clinical patients with inflammation and cancer for many years in China. The purpose of
Yiping Ren et al.
Journal of immunology (Baltimore, Md. : 1950), 181(2), 1491-1498 (2008-07-09)
Berbamine (BM) is an herbal compound derived from Berberis vulgaris L commonly used in traditional Chinese medicine. In this study, we show that BM has potent anti-inflammatory properties through novel regulatory mechanisms, leading to reduced encephalitogenic T cell responses and
Xiao-ying Zhao et al.
Chinese medical journal, 120(9), 802-806 (2007-05-29)
Currently, resistance and relapse are still major problems in acute promyelocytic leukemia (APL) cases. Thus, new agents that override the resistance are crucial to the development of curative therapies for APL. In this study, we investigated the effects of berbamine
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