SECURININE 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)

Safety Information

Hazard Codes 

T,Xn

Risk Statements 

23/24/25-22

Safety Statements 

36/37/39-45

WGK Germany 

3

RTECS 

VS4115000

SECURININE 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

GABAA receptor blocker, CNS stimulant

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.

Definition

ChEBI: Securinine is a member of indolizines.

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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