5380. Laudanine

Nomenclature

CAS number: 85-64-3
2-Methoxy-5-[(1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl]phenol; dl-laudanidine.
C20H25NO4; mol wt 343.42.
C 69.95%, H 7.34%, N 4.08%, O 18.64%.

Description and references

In the alkaline mother liquors from morphine extraction, in amounts corresp to about 0.005% of the opium employed: L. F. Small, R. E. Lutz, Chemistry of the Opium Alkaloids, Supplement No. 103, Public Health Reports, Washington (1932) p 34. Structure: Spth, Monatsh. Chem. 41, 297 (1920). Synthesis: Spth, Lang, ibid. 42, 273 (1921); Frydman et al., Tetrahedron 4, 342 (1958).

Chemical structure

Properties

Orthorhombic prisms from alcohol or chloroform, mp 167°. d420 1.26. uv max: 284 nm (log ε 3.78). Sol in benzene, chloroform, hot alcohol; sparingly sol in ether. Practically insol in water.