Title: Vomicine
CAS Registry Number: 125-15-5
CAS Name: 4-Hydroxy-19-methyl-16,19-secostrychnidine-10,16-dione
Additional Names: 12-hydroxy-N-methylpseudostrychnine
Molecular Formula: C22H24N2O4
Molecular Weight: 380.44
Percent Composition: C 69.46%, H 6.36%, N 7.36%, O 16.82%
Literature References: From seed of Strychnos nux vomica L., Loganiaceae: Wieland, Oertel, Ann. 469, 193 (1929). Structure: Huisgen et al., ibid. 573, 121 (1951). Synthesis: Rosenmund, Angew. Chem. 75, 1127 (1963). Reviews: R. Robinson in Progress in Organic Chemistry vol. I (Butterworths, London, 1952) pp 2-21; J. B. Hendrickson in The Alkaloids vol. VI, R. H. F. Manske, H. L. Holmes, Eds. (Academic Press, New York, 1960) pp 195-204.
Properties: Hexagonal prisms from acetone, mp 284°. [a]D22 +80° (c = 0.5 in alc). Weak, mono-acidic base forming salts with an acid reaction. Freely sol in chloroform, sol in hot alcohol, acetone, slightly in ether, ethyl acetate.
Melting point: mp 284°
Optical Rotation: [a]D22 +80° (c = 0.5 in alc)
Derivative Type: Hydrochloride
Molecular Formula: C22H24N2O4.HCl
Molecular Weight: 416.90
Percent Composition: C 63.38%, H 6.04%, N 6.72%, O 15.35%, Cl 8.50%
Properties: Prisms from water, dec 245°. uv max (ethanol): 222, 263, 297 nm (log e 4.27, 3.77, 3.52). Sparingly sol in water.
Absorption maximum: uv max (ethanol): 222, 263, 297 nm (log e 4.27, 3.77, 3.52)
Derivative Type: Methyl ether
Molecular Formula: C23H26N2O4
Molecular Weight: 394.46
Percent Composition: C 70.03%, H 6.64%, N 7.10%, O 16.22%
Properties: Needles from alcohol, dec 290°. [a]D20 +16° (c = 0.5 in alcohol).
Optical Rotation: [a]D20 +16° (c = 0.5 in alcohol)
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