5381. Laudanosine

Nomenclature

CAS number: 2688-77-9
(1S)-1-[(3,4-Dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline; 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinoline; N-methyltetrahydropapaverine.
C21H27NO4; mol wt 357.44.
C 70.56%, H 7.61%, N 3.92%, O 17.90%.

Description and references

Occurs in opium (0.0008%). It is the last alkaloid to be separated from morphine extraction mother liquors; occurs as (+)-form. Synthesis: Pictet, Finkelstein, Ber. 42, 1979 (1909); Frydman et al., Tetrahedron 4, 342 (1958); Elliott, J. Heterocycl. Chem. 9, 853 (1972). Asymmetric synthesis: M. Konda et al., Chem. Pharm. Bull. 23, 1025 (1975); of (R)-()-laudanosine: M. Konda et al., ibid. 25, 69 (1977); R. E. Gawley, G. A. Smith, Tetrahedron Lett. 29, 301 (1988). Configuration: Leithe, Ber. 64, 2827 (1931); Faltis, Adler, Arch. Pharm. 284, 281 (1951); Corrodi, Hardegger, Helv. Chim. Acta 39, 889 (1956).

Chemical structure

Properties

Crystals from light petr (30-60°), mp 89°. [α]D16 +106° (c = 1.6 in 97% alc); [α]D16 +130° (chloroform); [α]D22 +52.2 ±1.3° (chloroform). [α]D20 +82.5° (ethanol). Absorption spectrum: Dobbie, Lauder, J. Chem. Soc. 83, 626 (1903). Practically insol in water. Freely sol in alcohol, chloroform, ether, hot petr ether.

Derivative

()-Form.

Properties

Colorless needles from ethanol, mp 83-85°. [α]D20 84.8° (c = 0.466 in ethanol).

Derivative

(±)-Form.

Properties

Crystals from dil alc, mp 114-115.5°.