Securinine
Title: Securinine
CAS Registry Number: 5610-40-2
CAS Name: Securinan-11-one
Molecular Formula: C13H15NO2
Molecular Weight: 217.26
Percent Composition: C 71.87%, H 6.96%, N 6.45%, O 14.73%
Literature References: From leaves and roots of Securinega suffruticosa Rehder, Euphorbiaceae found in the Ussuri region: Murav'eva, Ban'kovskii, C.A. 50, 17335c (1956); eidem, Dokl. Akad. Nauk SSSR 110, 998 (1956), C.A. 51, 8121a (1957). Improved extraction process: Kogan et al., GB 116947l (1959 to All-Union Sci. Res. Inst. of Medicinal Plants), C.A. 72, 47349x (1970) corresp to US 3538103 (1970). Structure: Satoda et al., Tetrahedron Lett. 1962, 1199; Mukherjee et al., Naturwissenschaften 50, 155 (1963); Saito et al., Tetrahedron 19, 2085 (1963). Stereochemistry: Nakano et al., Chem. Ind. (London) 1963, 1034; Parello et al., Bull. Soc. Chim. Fr. 1963, 898; Nakano et al., J. Org. Chem. 28, 2619 (1963); Horii et al., Tetrahedron 19, 2101 (1963); Imado et al., Chem. Ind. (London) 1964, 1691. Synthesis of the racemate: Saito et al., Chem. Pharm. Bull. 14, 313, 1059 (1966); Horii et al., Tetrahedron 23, 1165 (1967). Toxicology study: S. L. Friess et al., Toxicol. Appl. Pharmacol. 3, 347 (1961).
Properties: Yellow crystals from alcohol, mp 142-143°. [a]D20 -1042° (c = 1 in alc). uv max (alc): 256, 330 nm (log e 4.27, 3.30).
Melting point: mp 142-143°
Optical Rotation: [a]D20 -1042° (c = 1 in alc)
Absorption maximum: uv max (alc): 256, 330 nm (log e 4.27, 3.30)
 
Derivative Type: Hydrochloride
Properties: mp 230°. [a]D20 -259.2° (alcohol).
Melting point: mp 230°
Optical Rotation: [a]D20 -259.2° (alcohol)
 
Derivative Type: Nitrate
Properties: mp 205°. [a]D20 -312.12° (alcohol). LD50 i.v. in mice: 3.5 ± 0.9 mg/kg (Friess).
Melting point: mp 205°
Optical Rotation: [a]D20 -312.12° (alcohol)
Toxicity data: LD50 i.v. in mice: 3.5 ± 0.9 mg/kg (Friess)

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