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399027

Sigma-Aldrich

Brucine

anhydrous, 98%

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Synonym(s):
10,11-Dimethoxystrychnine, 2,3-Dimethoxystrychnidin-10-one
Empirical Formula (Hill Notation):
C23H26N2O4
CAS Number:
357-57-3
Molecular Weight:
394.46
Beilstein:
63046
EC Number:
206-614-7
MDL number:
MFCD00005942
UNSPSC Code:
12352210
PubChem Substance ID:
24864782
NACRES:
NA.22

grade

anhydrous

Quality Level

200

Assay

98%

optical activity

[α]20/D −118°, c = 2.5 in chloroform

mp

175-178 °C (dec.) (lit.)

SMILES string

[H][C@@]12CC(=O)N3c4cc(OC)c(OC)cc4[C@]56CC[N@H]7CC(=CCO1)[C@]([H])(C[C@@H]57)[C@]2([H])[C@]36[H]

InChI

1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1

InChI key

RRKTZKIUPZVBMF-IBTVXLQLSA-N

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General description

Brucine is the major active pharmacological component of Strychnos nux-vomica seeds, which is known for its anti-inflammatory and analgesic activities.

Application

Brucine may be used as chiral resolving agent for the optical resolution of tertiary acetylenic alcohols into enantiomers.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H330,H412

Hazard Classifications

Acute Tox. 1 Oral - Acute Tox. 2 Inhalation - Aquatic Chronic 3

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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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A Novel Brucine Gel Transdermal Delivery System Designed for Anti-Inflammatory and Analgesic Activities.
Wu P, et al.
International Journal of Molecular Medicine, 18(4), 757-757 (2017)
Mohsen Behpour et al.
Phytochemical analysis : PCA, 23(2), 95-102 (2011-05-28)
Strychnos nux-vomica L. (Loganiaceae), widely used in folk medicine, is grown extensively in southern Asian countries. Its major bioactive constituents are strychnine and brucine, which are frequently used in traditional herbal medicines for treatment of nervous diseases, vomiting and traumatic
S S Agrawal et al.
Life sciences, 89(5-6), 147-158 (2011-06-21)
Brucine (BRU), a natural plant alkaloid is reported to possess cytotoxic and antiproliferative activities. In this study we aimed to investigate its in vitro and in vivo antitumor and antiangiogenic effects. Cell proliferation and viability was assessed using microculture tetrazolium
Hong-Mei Zhang et al.
Molecular biology reports, 39(4), 4937-4947 (2011-12-14)
The features of brucine (BC) binding to two blood proteins, bovine hemoglobin (BHb), and bovine serum albumin (BSA), were investigated via fluorescence, circular dichroism and UV/Vis absorption spectroscopy. The results revealed that BC caused the fluorescence quenching of blood proteins
Jun Chen et al.
Fitoterapia, 82(8), 1302-1308 (2011-10-01)
The toxicity depending on both dose and administration route is the major obstacle to the development of brucine, a bioactive alkaloid from Semen Strychni. In this study, the apparent partition coefficient and plasma protein binding extent of brucine were determined.
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