8737. Sparteine

Nomenclature

CAS number: 90-39-1
[7S-(7α,7aα,14α,14aβ)]-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1′,2′-e][1,5]diazocine; l-sparteine; lupinidine.
C15H26N2; mol wt 234.38.
C 76.87%, H 11.18%, N 11.95%.

Description and 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); Schpf 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.

Chemical structure

Properties

Viscous, oily liquid. bp8 173°. Volatile with steam. [α]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.

Derivative

Sulfate pentahydrate.

Nomenclature

CAS number: 6160-12-9
Depasan (Giulini); Tocosamine (Trent).
C15H26N2.H2SO4.5H2O; mol wt 422.54.
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

l-α-Isosparteine.

Nomenclature

CAS number: 446-95-7
Genisteine (alkaloid).

Description and references

14aα-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°. [α]D22 51.6° (c = 0.7 in abs. ethanol).

Therapeutic Category

In treatment of cardiac insufficiency.