5619. Lycodine

Nomenclature

CAS number: 20316-18-1
[4aR-(4aα,5α,10bα,12R*)]-2,3,4,4a,5,6-Hexahydro-12-methyl-1H-5,10b-propano-1,7-phenanthroline.
C16H22N2; mol wt 242.36.
C 79.29%, H 9.15%, N 11.56%.

Description and references

Isoln from Lycopodium annotinum L., Lycopodiaceae: F. A. L. Anet, C. R. Eves, Can. J. Chem. 36, 902 (1958). Structure: W. A. Ayer, G. G. Iverach, ibid. 38, 1823 (1960); F. A. L. Anet, M. V. Rao, Tetrahedron Lett. 1960, 9. Synthesis of (±)-form: E. Kleinman, C. H. Heathcock, ibid. 1979, 4125; C. H. Heathcock et al., J. Am. Chem. Soc. 104, 1054 (1982).

Chemical structure

Properties

Cryst powder, mp 118-119°. [α]D -10° (c = 1.01 in ethanol). pKa′s 3.97, 8.08.