Title: Quinamine
CAS Registry Number: 464-85-7
CAS Name: [1S-[1a,2a(3aS*,8aR*),4a,5b]]-8a-(5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl)-2,3,8,8a-tetrahydro-3aH-furo[2,3-b]indol-3a-ol
Molecular Formula: C19H24N2O2
Molecular Weight: 312.41
Percent Composition: C 73.05%, H 7.74%, N 8.97%, O 10.24%
Literature References: In Cinchona barks, especially those of Cinchona pubescens Vahl. (C. succirubra Pav.) and C. officinalis L. (C. ledgeriana Moens), Rubiaceae: Hesse, Ber. 5, 265 (1872); 10, 2157 (1877); Ann. 207, 288 (1881); Oudemans, Ann. 197, 49 (1879). Isoln from quinine sulfate mother liquors: De Vrij, Pharm. J. 4, 609 (1874); Howard, ibid. 5, 1 (1875); Henry et al., J. Chem. Soc. 1945, 524. Reduction with lithium aluminum hydride yields cinchonamine: Goutarel et al., Helv. Chim. Acta 33, 150 (1950). Structure: Witkop, J. Am. Chem. Soc. 72, 2311 (1950).
Properties: Needles from boiling benzene, mp 185-186°. [a]D +116° or +104° (c = 0.5 in alcohol). uv max (methanol): 242, 301 nm (log e 3.93, 3.39). One gram dissolves in 1500 ml water, 50 ml ether, about 120 ml 80% alcohol. Sol in abs alc, hot ether, hot benzene, hot petr ether.
Melting point: mp 185-186°
Optical Rotation: [a]D +116° or +104° (c = 0.5 in alcohol)
Absorption maximum: uv max (methanol): 242, 301 nm (log e 3.93, 3.39)
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C19H25ClN2O2.H2O
Molecular Weight: 366.88
Percent Composition: C 62.20%, H 7.42%, Cl 9.66%, N 7.64%, O 13.08%
Properties: Crystals, mp 166-167°. [a]D +102.8°.
Melting point: mp 166-167°
Optical Rotation: [a]D +102.8°
Derivative Type: Hydriodide
Molecular Formula: C19H25IN2O2
Molecular Weight: 440.32
Percent Composition: C 51.83%, H 5.72%, I 28.82%, N 6.36%, O 7.27%
Properties: Crystals, mp 224°. [a]D +84.82° (c = 0.5 in alcohol).
Melting point: mp 224°
Optical Rotation: [a]D +84.82° (c = 0.5 in alcohol)
Derivative Type: Nitrate
Molecular Formula: C19H25N3O5
Molecular Weight: 375.42
Percent Composition: C 60.79%, H 6.71%, N 11.19%, O 21.31%
Properties: Crystals, mp 186-188°. [a]D +94.9°.
Melting point: mp 186-188°
Optical Rotation: [a]D +94.9°
Status: This monograph has been retired and is no longer subject to revision or update. |