2286. Cinchonidine

Nomenclature

CAS number: 485-71-2
(8α,9R)-Cinchonan-9-ol; cinchovatine; α-quinidine.
C19H22N2O; mol wt 294.39.
C 77.52%, H 7.53%, N 9.52%, O 5.43%.

Description and references

Occurs in most varieties of cinchona bark, especially in bark of Cinchona pubescens Vahl. (C. succirubra Pav.) and C. pitayensis Wedd., Rubiaceae. Isoln: Leers, Ann. 82, 147 (1852). Structure: Rabe, ibid. 365, 359 (1909). Stereoisomeric with cinchonine: Koenigs, ibid. 347, 182 (1906). Configuration: Prelog, Zalán, Helv. Chim. Acta 27, 535 (1944); Prelog, H"afliger, ibid. 33, 2021 (1950); Roth, Pharmazie 16, 257 (1961); Lyle, Keefer, Tetrahedron 23, 3253 (1967). Biosynthetic studies: Battersby, Parry, Chem. Commun. 1971, 31. Toxicity studies: C. C. Johnson, C. F. Poe, Acta Pharmacol. Toxicol. 4, 265 (1948); E. W. Schafer, Jr. et al., Ecotoxicol. Environ. Saf. 6, 149 (1982).

Chemical structure

Properties

Orthorhombic plates, prisms from alcohol, mp 210°. [α]D20 -109.2° (alc). uv absorption data: Kamath et al., Indian J. Chem. 6, 510 (1968). Sol in alcohol and chloroform; moderately sol in ether. Practically insol in water. pK1 5.80, pK2 10.03. Protect from light. LD50 i.p. in rats: 206 mg/kg (Johnson, Poe). LD50 orally in quail: >316 mg/kg (Schafer).

Derivative

Dihydrochloride.
C19H22N2O.2HCl; mol wt 367.31.
C 62.13%, H 6.59%, N 7.63%, O 4.36%, Cl 19.30%.

Properties

White or slightly yellow crystals or powder. Freely sol in water or alcohol. Protect from light.

Derivative

Hydrochloride dihydrate.
C19H22N2O.HCl.2H2O; mol wt 366.88.
C 62.20%, H 7.42%, N 7.64%, O 13.08%, Cl 9.66%.

Properties

Cryst powder; loses all of its H2O at 120°. [α]D20 -117.5° (water). Sol in 25 parts cold water, more sol in boiling water; sol in alcohol, chloroform, slightly in ether. The aq soln is practically neutral. Protect from light.

Derivative

Sulfate trihydrate.
(C19H22N2O)2.H2SO4.3H2O; mol wt 740.91.
C 61.60%, H 7.07%, N 7.56%, O 19.43%, S 4.33%.

Properties

Silky, acicular crystals; efflorescent on exposure to air and darkens in light. mp when anhydr ≈240° with decompn. One gram dissolves in 70 ml water, 20 ml hot water, 90 ml alcohol, 40 ml hot alc, 620 ml chloroform. Practically insol in ether. The aq soln is practically neutral. Protect from light.

Derivative

Epicinchonidine.

Nomenclature

CAS number: 550-54-9
(8α,9S)-Cinchonan-9-ol.

Properties

mp 104°, [α]D20 +63° (c = 0.804 in alc): Rabe et al., Ann. 492, 253 (1932).

Therapeutic Category

Antimalarial.

Keywords

Antimalarial