Sparteine
Title: Sparteine
CAS Registry Number: 90-39-1
CAS Name: [7S-(7a,7aa,14a,14ab)]-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1¢,2¢-e][1,5]diazocine
Additional Names: l-sparteine; lupinidine
Molecular Formula: C15H26N2
Molecular Weight: 234.38
Percent Composition: C 76.87%, H 11.18%, N 11.95%
Literature References: In yellow and black lupin beans, Lupinus luteus L. and L. niger Hort.; also in Cytisus scoparius (L.) Link. and Anagyris foetida L., Leguminosae. Extraction procedure: Karrer et al., Helv. Chim. Acta 11, 1062 (1928). Structure: Clemo et al., J. Chem. Soc. 1931, 429; Ing, ibid. 1933, 504; Schirm, Besendorf, Arch. Pharm. 280, 64 (1942); Galinovsky, Stern, Ber. 77B, 132 (1944); Clemo et al., J. Chem. Soc. 1949, 663. Biosynthesis: Anet et al., Nature 165, 35 (1950); Schöpf et al., Angew. Chem. 65, 161 (1953); 69, 69 (1957); van Tamelen, Foltz, J. Am. Chem. Soc. 82, 2400 (1960). Absolute configuration: Okuda et al., Chem. Ind. (London) 1961, 1116. Conformation: Bohlmann et al., Tetrahedron Lett. 1965, 2705; Wiewiorowski et al., Can. J. Chem. 45, 1447 (1967). Synthesis of racemate: Bohlmann et al., Ber. 106, 3026 (1973); N. Takatsu et al., Chem. Pharm. Bull. 35 4990 (1987). Chemistry: Binnig, Arzneim.-Forsch. 24, 752 (1974). Studies of cardiovascular effects: Raschak, ibid. 753.
Properties: Viscous, oily liquid. bp8 173°. Volatile with steam. [a]D21 -16.4° (c = 10 in abs alc). nD20 1.5312. d420 1.020. pK1 at 20°: 2.24; pK2: 9.46; pH of 0.01 molar soln 11.6. One gram dissolves in 325 ml water. Freely sol in alcohol, chloroform or ether.
Boiling point: bp8 173°
pKa: pK1 at 20°: 2.24; pK2: 9.46; pH of 0.01 molar soln 11.6
Optical Rotation: [a]D21 -16.4° (c = 10 in abs alc)
Index of refraction: nD20 1.5312
Density: d420 1.020
 
Derivative Type: Sulfate pentahydrate
CAS Registry Number: 6160-12-9
Trademarks: Depasan (Giulini); Tocosamine (Trent)
Molecular Formula: C15H26N2.H2SO4.5H2O
Molecular Weight: 422.54
Percent Composition: C 42.64%, H 9.06%, N 6.63%, S 7.59%, O 34.08%
Properties: Columnar crystals, loses water of crystn at 100° turning brown, dec 136°. pH of 0.05 molar soln 3.3. One gram dissolves in 1.1 ml water, 3 ml alcohol. Practically insol in chloroform and ether.
 
Derivative Type: l-a-Isosparteine
CAS Registry Number: 446-95-7
Additional Names: Genisteine (alkaloid)
Literature References: 14aa-stereoisomer. Isoln from Cytisus scoparius (L.) Link, (Spartium scoparium L.), Leguminosae: Valeur, Compt. Rend. 167, 23, 163 (1918); from Lupinus caudatus Kellog, Leguminosae: Marion et al., Can. J. Chem. 29, 22 (1951). Identity as stereoisomer: Marion, Leonard, ibid. 297. Structure: Leonard et al., J. Am. Chem. Soc. 77, 1552 (1955). Absolute configuration: Okuda, Tsuda, Chem. Ind. (London) 1961, 1115.
Properties: Monohydrate, needles from boiling acetone, mp 108-110°. [a]D22 -51.6° (c = 0.7 in abs. ethanol).
Melting point: mp 108-110°
Optical Rotation: [a]D22 -51.6° (c = 0.7 in abs. ethanol)
 
Therap-Cat: In treatment of cardiac insufficiency.

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