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SECURININE

SECURININE Structure
CAS No.
5610-40-2
Chemical Name:
SECURININE
Synonyms
securinin;SECURININE;Securan one;(-)-securinin;(-)-Securinin;SECURAN-11-ONE;SECURININE(RG);(-)-SECURININE;(–)-Securinine;Securinan-11-on
CBNumber:
CB8247560
Molecular Formula:
C13H15NO2
Molecular Weight:
217.26
MOL File:
5610-40-2.mol
Modify Date:
2023/9/20 16:43:00

SECURININE 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

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P405-P501
Hazard Codes  T,Xn
Risk Statements  23/24/25-22
Safety Statements  36/37/39-45
WGK Germany  3
RTECS  VS4115000
NFPA 704
0
2 0

SECURININE Chemical Properties,Uses,Production

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]20D - 1106°(CHC13), [α]30D - 1106°(CHC13) and[α]20D - 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.

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)

SECURININE Preparation Products And Raw materials

Raw materials

Preparation Products

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SECURININE Spectrum

SECURAN-11-ONE SECURININE (-)-securinin securinan-11-one securinin Securinan-11-on SECURININE(RG) (6S,11aR,11bS)-9,10,11,11a-Tetrahydro-8H-6,11b-Methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one 1,2,3,4,10,10a-Hexahydro-10-hydroxy- (2β,7S,9S)-Securinan-11-one Securan one (-)-SECURININE Securinine, 98%, from Flueggea suffruticosa (Pall.) Baill. 8H-6,11b-Methanofuro[2,3-c]pyrido[1,2-a]azepin-2(6H)-one, 9,10,11,11a-tetrahydro-, (6S,11aR,11bS)- (–)-Securinine SECURININE USP/EP/BP (-)-Securinin 5610-40-2 Heterocycles Intermediates & Fine Chemicals Pharmaceuticals