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Merck
CN

SML0055

Securinine

≥98% (HPLC)

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About This Item

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

Key Documents

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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

SMILES string

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

InChI key

SWZMSZQQJRKFBP-WZRBSPASSA-N

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

Quality Level

100

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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 a GABAA receptor antagonist which has been found to increase p73 protein expression
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

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
061M4718V

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S Liras et al.
Organic letters, 3(5), 703-706 (2001-03-22)
[structure: see text]. The concise total synthesis of securinine in nine steps from readily available starting materials is described. Key steps of the synthesis include an addition of a silyloxyfuran to an in situ generated iminium ion and a novel
Wei Yuan et al.
Natural product research, 21(3), 234-242 (2007-03-17)
Investigations on callus cultures of Securinega suffruticosa indicated that the cell line of S. suffruticosa callus was able to accumulate four known Securinega alkaloids with dextro rotation but not levo rotation as reported before: virosecurinine (1), viroallosecurinine (2), 14,15-dihydrovirosecurinine (3)
Hong Guan et al.
Biotechnology letters, 27(16), 1189-1193 (2005-09-15)
A new isolate of Aspergillus sp. hydrogenated the gamma,delta-double bond of securinine (143 mg l(-1)) to give 14,15-dihydrosecurinine at over 98% (w/w) yield after 8 h. It also hydrogenated the C11(13) double bond of 3-hydroxy-1(10),3,11(13)-guaiatriene-12,6-olide-2-one (HGT) (200 mg l(-1)) to
Kalpana Gupta et al.
PloS one, 6(6), e21203-e21203 (2011-07-07)
As the defining feature of Acute Myeloid Leukemia (AML) is a maturation arrest, a highly desirable therapeutic strategy is to induce leukemic cell maturation. This therapeutic strategy has the potential of avoiding the significant side effects that occur with the
Matt Shipman et al.
PloS one, 7(9), e41278-e41278 (2012-10-03)
Securinine, a GABA(A) receptor antagonist, has been reported to enhance monocyte cell killing of Coxiella burnetii without obvious adverse effects in vivo. We employed multiplex 2D gel electrophoresis using Zdyes, a new generation of covalently linked fluorescent differential protein detection
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