Title: Cinchonamine
CAS Registry Number: 482-28-0
CAS Name: [1S-(1a,2a,4a,5b)]-2-(5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl)-1H-indole-3-ethanol
Additional Names: 3-(b-hydroxyethyl)-2-(5-vinyl-2-quinuclidyl)indole
Molecular Formula: C19H24N2O
Molecular Weight: 296.41
Percent Composition: C 76.99%, H 8.16%, N 9.45%, O 5.40%
Literature References: From the bark of Remijia purdieana Wedd., Rubiaceae: Arnaud, Compt. Rend. 93, 593 (1881); Hesse, Ann. 225, 211 (1884). Prepn by reduction of quinamine with lithium aluminum hydride and structure: Goutarel et al., Helv. Chim. Acta 33, 150 (1950). Synthesis: Chen et al., C.A. 53, 7219e (1959). Total synthesis: G. Grethe et al., Helv. Chim. Acta 59, 2271 (1976). Stereochemistry: Wenkert, Bringi, J. Am. Chem. Soc. 80, 3484 (1958); Augustine, Chem. Ind. (London) 1959, 1071; Sawa, Matsumura, Tetrahedron 26, 2923 (1970). Biosynthetic studies: Battersby, Parry, Chem. Commun. 1971, 31. Conversion of chinchona alkaloids of the quinoline series to those of the indole series: Ochiai et al., C.A. 59, 14040h (1963).
Properties: Triboluminescent, orthorhombic prisms from methanol, mp 186°, also reported as mp 194°. [a]D20 +123° (c = 0.66 in ethanol). pK in 80% methyl Cellosolve: 8.28. uv max (methanol): 223, 292 nm (log e 4.60, 3.88). One gram dissolves in about 35 ml alcohol, 105 ml ether. Sol in benzene, chloroform, petr ether, CS2; practically insol in water.
Melting point: mp 186°; mp 194°
pKa: pK in 80% methyl Cellosolve: 8.28
Optical Rotation: [a]D20 +123° (c = 0.66 in ethanol)
Absorption maximum: uv max (methanol): 223, 292 nm (log e 4.60, 3.88)
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C19H24N2O.HCl.H2O
Molecular Weight: 350.88
Percent Composition: C 65.04%, H 7.76%, N 7.98%, O 9.12%, Cl 10.10%
Properties: Cubic crystals. One gram dissolves in 200 ml water. Sol in alc.
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