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SML0055

Sigma-Aldrich

Securinine

≥98% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C13H15NO2
CAS Number:
5610-40-2
Molecular Weight:
217.26
MDL number:
MFCD00078775
UNSPSC Code:
12352200
PubChem Substance ID:
329825122

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -980 to -1015 (C=1, MeOH)

color

yellow

solubility

DMSO: ≥25 mg/mL

storage temp.

2-8°C

SMILES string

O=C1O[C@@]23C[C@@H](C=CC2=C1)N4CCCC[C@H]34

InChI

1S/C13H15NO2/c15-12-7-9-4-5-10-8-13(9,16-12)11-3-1-2-6-14(10)11/h4-5,7,10-11H,1-3,6,8H2/t10-,11-,13+/m1/s1

InChI key

SWZMSZQQJRKFBP-WZRBSPASSA-N

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Application

Securinine was used as a standard in the synthesis of the members of Securinega alkaloid family.

Biochem/physiol Actions

Securinine is an alkaloid widely in traditional folk medicine. Long known as a GABAA antagonist, securinine was recently found to up-regulate p53 protein and to modulate the related family member p73 protein in a p53-dependent fashion, inducing p73 in the HCT116 p53(-) cells and down-regulating it in the p53(+) cells. Induction of proapoptotic protein p73 only in p53 cells could be used to target cancer cells preferentially. Securinine has been found to induce p53-independent, p73-dependent apoptosis in RKO colon cancer cells.

Features and Benefits

This compound is featured on the GABAA Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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H Pu et al.
Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials, 24(4), 278-280 (2003-02-18)
Pharmacological activities of virosecurinine (Vse) and securinine (Sec) were studied. The results showed that acute toxicity of Vse was 1/13.6 that of Sec, and Vse had no convulsive effects on rats or frogs, while Sec had. The results also showed
David González-Gálvez et al.
The Journal of organic chemistry, 74(16), 6199-6211 (2009-07-25)
The most representative securinega alkaloids have been synthesized through a new strategy involving the palladium-catalyzed enantioselective allylation of a cyclic imide, a vinylogous Mannich reaction, and a ring-closing metathesis process, as the key steps. The diastereoselectivity of the vinylogous Mannich
Kirk Lubick et al.
Journal of leukocyte biology, 82(5), 1062-1069 (2007-08-19)
Innate immune cell stimulation represents a complementary approach to vaccines and antimicrobial drugs to counter infectious disease. We have used assays of macrophage activation and in vitro and in vivo phase II Coxiella burnetii infection models to compare and contrast
Michael Holmes et al.
Experimental parasitology, 127(2), 370-375 (2010-09-14)
Securinine, an alkaloid originally isolated from Securinega suffruticosa, exhibits a wide range of biological activities, including anti-malarial activity. Along with securinine, 10 pyrrolidine derivatives, generated via the retrosynthesis of (-)-securinine, were selected and tested for their inhibitory activity against Toxoplasma
Jung-Hsuan Chen et al.
Organic letters, 14(17), 4531-4533 (2012-08-24)
Total syntheses of (±)-securinine and (±)-allosecurinine that employ a tandem rhodium carbenoid-initiated Claisen/α-ketol rearrangement sequence as a key step are described.
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