5379. Laudanidine

Nomenclature

CAS number: 301-21-3
2-Methoxy-5-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]phenol; l-laudanine; tritopine.
C20H25NO4; mol wt 343.42.
C 69.95%, H 7.34%, N 4.08%, O 18.64%.

Description and references

The l-form of laudanine, q.v. Traces in opium: Hesse, Ann. 282, 208 (1894); Kauder, Arch. Pharm. 228, 419 (1890). Structure and synthesis: Spth, Bernhauer, Ber. 58, 200 (1925); Spth, Seka, ibid. 1272; Spth, Burger, Monatsh. Chem. 47, 733 (1926); Frydman et al., Tetrahedron 4, 342 (1958). Configuration: Corrodi, Hardegger, Helv. Chim. Acta 39, 889 (1956).

Properties

Prisms from alcohol, mp 185°. [α]D15 88° (p = 5 in chloroform). [α]D22 94.7 ± 1.3°. The hydrochloride is more sol than laudanine hydrochloride and makes possible a separation of the two alkaloids.