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

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

Different sources of media describe the Uses of 5610-40-2 differently. You can refer to the following data:
1. 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.
2. GABAA receptor blocker, CNS stimulant

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

Upstream product

• 651738-07-7 1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-3-bromo-9-oxa-8-oxobicyclo[4.3.0]nona-4,6-diene 
• 651737-98-3 1(S)-[(2'R)-N-tert-butoxycarbonylpiperidinyl]-1-ethynyl-4(Z)-hepten-1-ol 
• 1126784-60-8 (1'S,3'S,8a'R)-3'-((Z)-2-iodovinyl)-3',5',6',7',8',8a'-hexahydro-2'H,5H-spiro[furan-2,1'-indolizin]-5-one 
• 5890-59-5 (RS)-7a-(SR)-piperidin-2-yl-7,7a-dihydro-6H-benzofuran-2-one 
• 14140-68-2 (RS)-1-formyl-2-((SR)-2-oxo-6,7-dihydro-2H-benzofuran-7a-yl)-piperidine 
• 651737-96-1 1(S)-[(2''R)-N-tert-butoxycarbonylpiperidinyl]-1-(2'-trimethylsilylethynyl)-4(Z)-hepten-1-ol 
• 651737-99-4 1-tert-butoxycarbonyl-2(R)-[1'(S)-allyloxy-1'-ethynyl-4'(Z)-heptenyl]piperidine 
• 651738-03-3 1(S)-[1'-tert-butoxycarbonyl-2'(R)-piperidinyl]-9-oxabicyclo[4.3.0]nona-4,6-diene 
• 651737-95-0 1-tert-butoxycarbonyl-2(R)-[4'(Z)-heptenoyl]piperidine 
• 708260-76-8 tert-butyl (2R)-2-[(2S)-2-[(Z)-4-iodo-3-butenyl]-5(2H)-oxo-2-furyl]piperidine-1-carboxylate 
• 651738-04-4 tert-butyl (2R)-2-[(7aS)-2(6H)-oxo-7,7a-dihydro-7a-benzofuranyl]piperidine-1-carboxylate 
• 14140-69-3 (RS)-1-formyl-2-((7aSR)-6ξ-bromo-2-oxo-6,7-dihydro-2H-benzofuran-7ar-yl)-piperidine 

Downstream Products

• 42555-40-8 1β-amino-11-oxo-securinanium; 2,4,6-trimethyl-benzenesulfonate 
• 3909-79-3 Tetrahydrosecurinin 
• 1085244-06-9 (2β,15α)-14,15-dihydro-15-(4-phenylpiperazin-1-yl)securinan-11-one 
• 1085244-08-1 (2β,15α)-14,15-dihydro-15-[4-(4-methoxyphenyl)piperazin-1-yl]securinan-11-one 

Relevant articles and documents

The asymmetric total synthesis of (-)-securinine

The alkaloid (-)-securinine was synthesized in 18 steps and 16% overall yield from trans-4-hydroxy-l-proline. The Royal Society of Chemistry.

First Diastereoselective Chiral Synthesis of (-)-Securinine

(Equation presented) A diastereoselective total synthesis of securinine in optically pure form was achieved by employing ring-closing metathesis of the corresponding dienyne compound as a key step.

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.