Cinchonine
Title: Cinchonine
CAS Registry Number: 118-10-5
CAS Name: (9S)-Cinchonan-9-ol
Molecular Formula: C19H22N2O
Molecular Weight: 294.39
Percent Composition: C 77.52%, H 7.53%, N 9.52%, O 5.43%
Literature References: Occurs in most varieties of cinchona bark, especially in bark of Cinchona micrantha R. & P., Rubiaceae. Isoln and structure: Rabe, Ber. 41, 63 (1908). Stereoisomeric with cinchonidine: Koenigs, Ann. 347, 182 (1906). Configuration: Prelog, Zalán, Helv. Chim. Acta 27, 535 (1944); Prelog, Häfliger, ibid. 33, 2021 (1950); Roth, Pharmazie 16, 257 (1961); Lyle, Keefer, Tetrahedron 23, 3253 (1967). Crystal and molecular structure: B. Oleksyn et al., Acta Crystallogr. B35, 440 (1979). Biosynthetic studies: Battersby, Parry, Chem. Commun. 1971, 31. Toxicity study: C. C. Johnson, C. F. Poe, Acta Pharmacol. Toxicol. 4, 265 (1949).
Properties: Prisms, needles from alcohol or ether. mp about 265°; begins to sublime at 220°. [a]D +229° (alcohol). uv absorption data: Kamath et al., Indian J. Chem. 6, 510 (1968). One gram dissolves in 60 ml alcohol, 25 ml boiling alcohol, 110 ml chloroform, 500 ml ether. Practically insol in water. pK1 5.85, pK2 9.92. Protect from light. LD50 i.p. in rats: 152 mg/kg (Johnson, Poe).
Melting point: mp about 265°
pKa: pK1 5.85, pK2 9.92
Optical Rotation: [a]D +229° (alcohol)
Toxicity data: LD50 i.p. in rats: 152 mg/kg (Johnson, Poe)
 
Derivative Type: Dihydrochloride
Molecular Formula: C19H22N2O.2HCl
Molecular Weight: 367.31
Percent Composition: C 62.13%, H 6.59%, N 7.63%, O 4.36%, Cl 19.30%
Properties: White or faintly yellow crystals or crystalline powder. Freely sol in water or alcohol. Protect from light.
 
Derivative Type: Hydrochloride dihydrate
Molecular Formula: C19H22N2O.HCl.2H2O
Molecular Weight: 366.88
Percent Composition: C 62.20%, H 7.42%, N 7.64%, O 13.08%, Cl 9.66%
Properties: Fine crystals. mp when anhydr about 215° with dec. One gram dissolves in 20 ml water, 3.5 ml boiling water, 1.5 ml alcohol, 20 ml chloroform; slightly sol in ether. The aq soln is practically neutral. Protect from light.
Melting point: mp when anhydr about 215° with dec
 
Derivative Type: Sulfate dihydrate
Molecular Formula: (C19H22N2O)2.H2SO4.2H2O
Molecular Weight: 722.89
Percent Composition: C 63.14%, H 6.97%, N 7.75%, O 17.71%, S 4.44%
Properties: Lustrous, very bitter crystals. mp when anhydr about 198°. One gram dissolves in 65 ml water, 30 ml hot water, 12.5 ml alc, 7 ml hot alc, 47 ml chloroform; slightly sol in ether. The aq soln is practically neutral.
Melting point: mp when anhydr about 198°
 
Derivative Type: Epicinchonine
CAS Registry Number: 485-70-1
CAS Name: (9R)-Cinchonan-9-ol
Properties: mp 83°, [a]D22 +120.3° (c = 0.806 in alc), Rabe et al., Ann. 492, 253 (1932).
Melting point: mp 83°
Optical Rotation: [a]D22 +120.3° (c = 0.806 in alc), Rabe et al., Ann. 492, 253 (1932)
 
Therap-Cat: Antimalarial.
Keywords: Antimalarial.

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