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399027

Sigma-Aldrich

Brucine

anhydrous, 98%

Synonym(s):

10,11-Dimethoxystrychnine, 2,3-Dimethoxystrychnidin-10-one

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About This Item

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

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

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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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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)
Bai-Can Yang et al.
International journal of nanomedicine, 6, 1109-1116 (2011-06-24)
To evaluate the pharmacokinetics and tissue distribution of liposomal brucine (LB) for dermal application. Pharmacokinetics and tissue distribution were studied by in vivo animal testing. High performance liquid chromatography (HPLC) was used to detect the concentration of brucine in rats'
Jun Chen et al.
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan, 131(5), 721-729 (2011-05-03)
A simple and low-cost HPLC method with UV absorbance detection was developed and validated to simultaneously determine strychnine and brucine, the most abundant alkaloids in the processed Semen Strychni, in rat tissues (kidney, liver, spleen, lung, heart, stomach, small intestine
Xueguo Chen et al.
Journal of analytical toxicology, 36(3), 171-176 (2012-03-16)
A liquid chromatography-electrospray ionization-ion trap mass spectrometry (LC-ESI-ITMS) method was developed for the simultaneous analysis of strychnine, brucine and their major metabolites. Strychnine and brucine were individually incubated with rat liver S9 fraction. The incubation samples were pooled together and
Jian-Min Qin et al.
International journal of nanomedicine, 7, 369-379 (2012-02-16)
Hepatocellular carcinoma is difficult to diagnose early, and most patients are already in the late stages of the disease when they are admitted to hospital. The total 5-year survival rate is less than 5%. Recent studies have showed that brucine
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