Title: Methylcytisine
CAS Registry Number: 486-86-2
CAS Name: (1R,5S)-1,2,3,4,5,6-Hexahydro-3-methyl-1,5-methano-8H-pyrido[1,2-a][1,5]diazocin-8-one
Additional Names: caulophylline; 12-methylcytisine; N-methylcytisine
Molecular Formula: C12H16N2O
Molecular Weight: 204.27
Percent Composition: C 70.56%, H 7.89%, N 13.71%, O 7.83%
Literature References: Lupine alkaloid of the quinolizidine type; occurring most abundantly in Leguminosae. Bioactive principle of blue cohosh, q.v. Isoln from Caulophyllum thalictroides Michx., Berberidaceae: F. B. Power, A. H. Salway, J. Chem. Soc. 103, 191 (1913); M. S. Flom et al., J. Pharm. Sci. 56, 1515 (1967); from Baptisia australis (L.) R. Br., Leguminosae: L. Marion, J. Ouellet, J. Am. Chem. Soc. 70, 691 (1948). Absolute configuration: S. Okuda et al., Chem. Pharm. Bull. 13, 491 (1965). Crystal structure: A. A. Freer et al., Acta Crystallogr. C43, 1119 (1987). Pharmacology: H. C. Ferguson, L. D. Edwards, J. Am. Pharm. Assoc. Sci. Ed. 43, 16 (1954). Toxicity study: R. B. Barlow, L. J. McLeod, Br. J. Pharmacol. 35, 161 (1969). Binding to nicotinic and muscarinic receptors: T. Schmeller et al., J. Nat. Prod. 57, 1316 (1994).
Properties: Colorless, prismatic needles from benzene + light petroleum, mp 137°. [a]30D -224° (c = 1.05 in water). uv max: 234, 309 nm (e 6860, 7560). Readily sol in water, alcohol, chloroform, benzene. LD50 in mice (mg/kg): 21 i.v.; 51 i.p. (Barlow, McLeod).
Melting point: mp 137°
Optical Rotation: [a]30D -224° (c = 1.05 in water)
Absorption maximum: uv max: 234, 309 nm (e 6860, 7560)
Toxicity data: LD50 in mice (mg/kg): 21 i.v.; 51 i.p. (Barlow, McLeod) |