Title: Isothebaine
CAS Registry Number: 568-21-8
CAS Name: (6aS)-5,6,6a,7-Tetrahydro-2,11-dimethoxy-6-methyl-4H-dibenzo[de,g]quinolin-1-ol
Additional Names: 2,11-dimethoxy-6aa-aporphin-1-ol; 1-hydroxy-2,11-dimethoxyaporphine
Molecular Formula: C19H21NO3
Molecular Weight: 311.37
Percent Composition: C 73.29%, H 6.80%, N 4.50%, O 15.42%
Literature References: Occurs as d-form in the root and whole plant of Papaver orientale L., Papaveraceae, collected in late autumn. Isoln: Gadamer, Arch. Pharm. 249, 39 (1911). Structure: Bentley, Blues, J. Chem. Soc. 1956, 1732; Bentley, Dyke, J. Org. Chem. 22, 429 (1957). Synthesis of dl-form: Battersby, Brown, Proc. Chem. Soc. London 1964, 85; H. Hara et al., Chem. Pharm. Bull. 29, 1083 (1981). Synthesis of natural and racemic forms: Battersby et al., J. Chem. Soc. 1965, 4550. Biosynthesis: eidem, Chem. Commun. 1965, 230.
Properties: Light-sensitive, rhombic crystals. mp 203-204°. [a]D18 +285° in alc. Sol in alcohol, chloroform, slightly in ether.
Melting point: mp 203-204°
Optical Rotation: [a]D18 +285° in alc |