Title: Apocodeine
CAS Registry Number: 641-36-1
CAS Name: (6aR)-5,6,6a,7-Tetrahydro-10-methoxy-6-methyl-4H-dibenzo[de,g]quinolin-11-ol
Additional Names: 10-methoxy-6ab-aporphin-11-ol
Molecular Formula: C18H19NO2
Molecular Weight: 281.35
Percent Composition: C 76.84%, H 6.81%, N 4.98%, O 11.37%
Literature References: A monomethyl ether of apomorphine, q.v. Prepd by heating codeine with oxalic acid: Folkers, J. Am. Chem. Soc. 58, 1814 (1936); by heating codeine with phosphoric acid: Small et al., J. Org. Chem. 5, 344 (1940). Configuration: Corrodi, Hardegger, Helv. Chim. Acta 38, 2038 (1955). Total synthesis and pharmacology: Neumeyer et al., J. Med. Chem. 16, 1223 (1973).
Properties: Small prisms from methanol (lose solvent at 80°/2 mm), mp 124° (dry). [a]D24 -97° (c = 0.45). Slightly soluble in water; sol in alcohol, ether, dilute acids.
Melting point: mp 124° (dry)
Optical Rotation: [a]D24 -97° (c = 0.45)
Derivative Type: Hydrochloride
Molecular Formula: C18H20ClNO2
Molecular Weight: 317.81
Percent Composition: C 68.03%, H 6.34%, Cl 11.16%, N 4.41%, O 10.07%
Properties: Crystals from alcohol-ether, softening 140°, dec 260-263°. [a]D22 -43° (c = 0.51). Very sol in water; sol in alcohol.
Optical Rotation: [a]D22 -43° (c = 0.51)
Therap-Cat: Emetic.
Keywords: Emetic. |