Quebrachamine
Structural Formula Vector Image
Title: Quebrachamine
CAS Registry Number: 4850-21-9
CAS Name: 7-Ethyl-1,4,5,6,7,8,9,10-octahydro-2H-3,7-methanoazacycloundecino[5,4-b]indole
Additional Names: kamassin
Molecular Formula: C19H26N2
Molecular Weight: 282.42
Percent Composition: C 80.80%, H 9.28%, N 9.92%
Literature References: From bark of Aspidosperma quebracho blanco Schlecht., Apocynaceae: Hesse, Ann. 211, 249 (1882); Field, J. Chem. Soc. 125, 1444 (1924). Identity with kamassin: Gellert, Witkop, Helv. Chim. Acta 35, 114 (1952). Structure: Witkop, J. Am. Chem. Soc. 79, 3193 (1957); Kny, Witkop, J. Org. Chem. 25, 635 (1960); Biemann, Spiteller, J. Am. Chem. Soc. 84, 4578 (1962). Crystal structure: C. Puglisi et al., Acta Crystallogr. B32, 1900 (1976). Total synthesis of dl-form: Stork, Dolfini, J. Am. Chem. Soc. 85, 2872 (1963); Ziegler et al., ibid. 91, 2342 (1969); Kutney et al., ibid. 92, 1727 (1970); V. S. Giri et al., J. Heterocycl. Chem. 17, 1133 (1980); S. Takano et al., Heterocycles 16, 247 (1981). Enantioselective synthesis: eidem, Chem. Commun. 1980, 616; 1981, 1153.
Properties: Bitter leaflets, mp 145-147°. [a]D20 -109 to -110° (acetone). uv max (methanol): 230, 287, 293 nm (log e 4.55, 3.85, 3.84). Sol in acetone, alc, chloroform, ether, dil acids.
Melting point: mp 145-147°
Optical Rotation: [a]D20 -109 to -110° (acetone)
Absorption maximum: uv max (methanol): 230, 287, 293 nm (log e 4.55, 3.85, 3.84)

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