5610-40-2

Basic information

• Product Name: SECURININE
• Synonyms: SECURAN-11-ONE;SECURININE;(-)-securinin;securinan-11-one;securinin;Securinan-11-on;SECURININE(RG);(2β,7S,9S)-Securinan-11-one
• CAS NO: 5610-40-2
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.26
• EINECS: 1308068-626-2
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 5610-40-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 140-1420C
• Boiling Point: 357.82°C (rough estimate)
• Flash Point: 197 ºC
• Appearance: yellow/
• Density: 1.30±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.32E-08mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO: ≥25mg/mL
• PKA: 8.29±0.20(Predicted)
• CAS DataBase Reference: SECURININE(CAS DataBase Reference)
• NIST Chemistry Reference: SECURININE(5610-40-2)
• EPA Substance Registry System: SECURININE(5610-40-2)

Safety Data

• Hazard Codes: T,Xn
• Statements: 23/24/25-22
• Safety Statements: 36/37/39-45
• WGK Germany: 3
• RTECS: VS4115000
• Hazardous Substances Data: 5610-40-2(Hazardous Substances Data)

Usage

Description

SECURININE, a yellow solid alkaloid, is a specific GABA receptor antagonist extracted from the leaves and roots of Securinega suffruticosa Rehder. It is known for its significant in vivo central nervous system (CNS) activity and is obtained as yellow crystals with strong levorotation properties.

Uses

Used in Pharmaceutical Industry:
SECURININE is used as a GABAA receptor blocker for its ability to modulate the activity of the central nervous system. It is particularly effective as a CNS stimulant, making it a valuable compound in the development of medications targeting various neurological conditions.
Used in Research and Development:
SECURININE is also utilized in research and development for its potential applications in understanding the role of GABA receptors in the CNS and their involvement in various neurological disorders. This knowledge can contribute to the development of novel therapeutic strategies and treatments for conditions such as anxiety, epilepsy, and other CNS-related diseases.

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)

InChI:InChI=1/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

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Downstream Products

• 42555-40-8 1β-amino-11-oxo-securinanium; 2,4,6-trimethyl-benzenesulfonate 
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Relevant articles and documents

Enantioselective approach to securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine

(Chemical Equation Presented) 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 meta

A new general access to either type of securinega alkaloids: Synthesis of securinine and (-)-allonorsecurinine

Matrix presented. The syntheses of securinine and (-)-allonorsecurinine have been achieved starting from easily available α-amino acid derivatives and using as key steps a RCM and a Heck reaction for the formation of rings D and C, respectively.

Kinetics and mechanism of the alkaline hydrolysis of securinine

The hydroxide ion-catalyzed hydrolysis of securinine involves the ring opening of the lactone moiety. The rate of hydrolysis is insensitive to the ionic strength. The observed pseudo-first-order rate constants reveal a decrease of approximately 4-fold due to the increase in the MeCN content from 4 to 50% (v/v) in mixed aqueous solvent. The temperature dependence of the rate of hydrolysis follows the Eyring equation, which yields ΔH* and ΔS* as 11.0 kcal mol-1 and -34.5 cal deg-1 mol-1, respectively. The hydroxy carboxylate product of the alkaline hydrolysis of securinine is shown to undergo cyclization in acidic medium to yield securinine. The observed pseudo-first-order rate constants for cyclization increase linearly with an increase in [H+]. The change in the content of MeCN from 3.8 to 47.2% (v/v) in mixed aqueous solvents does not show an effect on the rate of the cyclization reaction. The most plausible mechanisms for alkaline hydrolysis and acid cyclization reactions are also discussed.