1455. Brucine
Nomenclature
Description and references
Toxic alkaloid resembling strychnine. Isoln from Strychnos seeds (Strychnos nux-vomica L. and S. ignatii Berg., Loganiaceae): C. Hartwick, P. Geiger, Arch. Pharm. 239, 491 (1901). Prepn from strychnine, q.v.: E. Tedeschi et al., Tetrahedron 24, 4573 (1968). 13C-NMR study: E. Wenkert et al., J. Org. Chem. 43, 1099 (1978). Electrophoretic determn in seeds: Y.-Y. Zong, C. Che, Planta Med. 61, 456 (1995). Toxicity data: M. H. Malone et al., J. Ethnopharmacol. 35, 295 (1992). Use as reagent for sulfur compounds: M. K. Tummuru et al., Analyst 109, 1105 (1984); for nitrates: J. Masini et al., Anal. Chem. 69, 1077 (1997). Review of structural elucidation: H. L. Holmes, Elucidation of the Structure of Strychnine and Brucine in The Alkaloids vol. I, R. H. F. Manske, Ed. (Academic Press, New York, 1950) pp 377-420.
Properties
Needles from acetone + water, mp 178°. [α]D 127° (chloroform), 85° (in abs alcohol). uv max (ethanol): 263, 301 nm (log ε 4.09, 3.93). Poisonous.Derivative
Tetrahydrate.Nomenclature
Properties
Monoclinic prisms. Also forms a dihydrate. Very bitter taste. Bitterness threshold 1:220,000. Handle dry powder in hood only. Becomes anhydr at 100°. One gram dissolves in 0.8 ml methanol, 1.3 ml alcohol, 5 ml chloroform, 25 ml ethyl acetate, 36 ml glycerol, about 100 ml benzene, 187 ml ether, 1320 ml water, 750 ml boiling water. pH of satd water soln 9.5. pK1 6.04, pK2 11.7. LD50 in mice (mg/kg): 12.0 i.v.; 62.0 i.p.; 150.0 orally (Malone).Derivative
Sulfate heptahydrate.Nomenclature
Use
Denaturing alcohol and oils; for separating racemic mixtures. Addition agent to lubricants. In analytical chemistry for determn of nitrate.Therapeutic Category
CNS stimulant.
Keywords
CNS Stimulant