740. Apocodeine
Nomenclature
CAS number: 641-36-1
(6aR)-5,6,6a,7-Tetrahydro-10-methoxy-6-methyl-4H-dibenzo[de,g]quinolin-11-ol; 10-methoxy-6aβ-aporphin-11-ol. C18H19NO2; mol wt 281.35.
C 76.84%, H 6.81%, N 4.98%, O 11.37%.
Description and 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). [α]D24 97° (c = 0.45). Slightly soluble in water; sol in alcohol, ether, dilute acids.Derivative
Hydrochloride.C18H20ClNO2; mol wt 317.81.
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°. [α]D22 43° (c = 0.51). Very sol in water; sol in alcohol.Therapeutic Category
Emetic.
Keywords
Emetic