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SECURININE

Product NameSECURININE
CAS5610-40-2
MFC13H15NO2
MW217.26
EINECS694-738-6
MOL File5610-40-2.mol

Chemical Properties

Melting point	140-1420C
alpha	D20 -1042° (c = 1 in alc)
Boiling point	357.82°C (rough estimate)
Density	1.30±0.1 g/cm3 (20 ºC 760 Torr)
refractive index	1.5300 (estimate)
storage temp.	Sealed in dry,2-8°C
solubility	DMSO: ≥25mg/mL
form	powder
pka	8.29±0.20(Predicted)
color	yellow
optical activity	[α]/D -980 to -1015 (C=1, MeOH)
InChI	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
InChIKey	SWZMSZQQJRKFBP-WZRBSPASSA-N
SMILES	N12CCCC[C@]1([H])[C@]13C[C@@]2([H])C=CC1=CC(=O)O3

Safety Information

Hazard Codes	T,Xn
Risk Statements	23/24/25-22
Safety Statements	36/37/39-45
WGK Germany	3
RTECS	VS4115000

Usage And Synthesis

Description

A constituent of the leaves of Securinega suffructicosa Rehd., the base also occurs in Phyllanthus disco ides. It is obtained as yellow crystals and is strongly laevorotatory having [α]²⁰_D - 1106°(CHC1₃), [α]³⁰_D - 1106°(CHC1₃) and[α]²⁰_D - 1042° (c 1.0, EtOH). The alkaloid yields a crystalline methiodide, m.p. 235-6°C.

Chemical Properties

Yellow Solid

Uses

Extracted from leaves and roots of Securinega suffruticosa Rehder. The most widely studied of these alkaloids, Securinine, is a specific GABA receptor antagonist and has been found to have significant in vivo CNS activity.

Uses

GABAA receptor blocker, CNS stimulant

Definition

ChEBI: Securinine is a member of indolizines.

in vivo

In this tumor model, tumor growth is significantly impaired with (-)-Securinine treatment indicating that (-)-Securinine has potential as an Acute Myeloid Leukemia (AML) therapeutic. (-)-Securinine treated mice (n=5 mice, bilateral tumors), exhibit an average of more than 75% smaller tumors than vehicle treated mice at the end of the study period^[2].

References

Murav'eva, Ban'kovskii., Dokl. Akad. Nauk, SSSR, 110,998 (1956)
Saito et al., Chem. & Ind., 1652 (1962)
Satoda et al., Tetrahedron Lett., 1199 (1962)
Mukherjee et al., Naturwiss., 50, 155 (1963)
Nakano et aI., Chem. & Ind., 1763 (1963)
Horii et al., ibid, 664 (1964)
Bevan et aI., ibid, 838 (1964)
Absolute configuration:
Bevan et al., Chern. Ind., 838 (1964)
Imadoetal., ibid, 1691 (1964)
Synthesis:
Horii et al., Tetrahedron, 23, 2265 (1967)

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