Title: Narcotoline
CAS Registry Number: 521-40-4
CAS Name: (3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-hydroxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranone
Additional Names: desmethylnarcotine
Molecular Formula: C21H21NO7
Molecular Weight: 399.39
Percent Composition: C 63.15%, H 5.30%, N 3.51%, O 28.04%
Literature References: Found in the shell of ripe poppyseed capsules: Wrede, Arch. Pharmacol. 184, 331 (1937); Baumgarten, Christ, Pharmazie 5, 80 (1950); Pfeifer, Weiss, ibid. 10, 658 (1955); from opium prepns: Pfeifer, Arch. Pharm. 290, 209 (1957). Preliminary stereochemical studies: Battersby, Spenser, J. Chem. Soc. 1965, 1087. Revised stereochemistry: Blaha et al., Collect. Czech. Chem. Commun. 29, 2328 (1964); Snatzke et al., Tetrahedron 25, 5059 (1969).
Properties: Rectangular rods from dil methanol, mp 202°. [a]D20 -189° (0.1 g in 25 ml chloroform, 20 cm tube). [a]D20 +5.8° (0.065 g in 5 ml 0.1N HCl in 20 cm tube). Very sparingly sol in water. Moderately sol in warm alc and ether. Freely sol in chloroform, in dil acids and in dil aq solns of KOH and NaOH. Sparingly sol in dil aq solns of Na2CO3.
Melting point: mp 202°
Optical Rotation: [a]D20 -189° (0.1 g in 25 ml chloroform, 20 cm tube); [a]D20 +5.8° (0.065 g in 5 ml 0.1N HCl in 20 cm tube) |