6423. Narcotoline

Nomenclature

CAS number: 521-40-4
(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; desmethylnarcotine.
C21H21NO7; mol wt 399.39.
C 63.15%, H 5.30%, N 3.51%, O 28.04%.

Description and 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).

Chemical structure

Properties

Rectangular rods from dil methanol, mp 202°. [α]D20 -189° (0.1 g in 25 ml chloroform, 20 cm tube). [α]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.