2491. Colubrines

C22H24N2O3; mol wt 364.44.
C 72.50%, H 6.64%, N 7.69%, O 13.17%.

Description and references

Minor alkaloids found in Strychnos nux vomica L.; naturally occurring in two chemically distinct forms, α and β. Isolation from mother liquor of commercial strychnine extraction: K. Warnat, Helv. Chim. Acta 14, 997 (1931). Isolation and characterization from S. nux vomica L.: G. B. Marini-Bettolo et al., J. Assoc. Off. Anal. Chem. 51, 185 (1968). Structure of α- and β-colubrine: S. P. Findlay, J. Am. Chem. Soc. 73, 3008 (1951); of β-colubrine: P. Rosenmund, Ber. 95, 2639 (1962); of α-colubrine: J. M. Culver, M. Sainsbury, J. Chem. Res. Synop. 1987, 304. Synthesis from strychnine: P. Rosenmund, H. Franke, Ber. 97, 1677 (1964). Determn by GLC: N. G. Bisset, P. Fouché, J. Chromatogr. 37, 172 (1968); by HPLC: G. M. Iskander et al., J. Liq. Chromatogr. 5, 1481 (1982). Chiroptical properties of β-colubrine: J. W. Snow, T. M. Hooker, Jr., Can. J. Chem. 56, 1222 (1978).

Chemical structure

Derivative

α-Colubrine.

Nomenclature

CAS number: 509-44-4
3-Methoxystrychnidin-10-one; 11-methoxystrychnine.

Properties

Pyramids from ethyl acetate, mp 189-193°. [α]D20 -72.4° (c = 0.9 in alc). uv max (ethanol): 255, 297 nm (log ε 4.03, 3.77). Sol in alc, benzene, chloroform.

Derivative

β-Colubrine.

Nomenclature

CAS number: 509-36-4
2-Methoxystrychnidin-10-one; 10-methoxystrychnine.

Properties

Crystals from dil alcohol, mp 222°. Very bitter. [α]D19 -107.7° (c = 2.5 in 80% alcohol). [α]D21 -156° (c = 0.042 in chloroform). uv max (ethanol): 262, 297 nm (log ε 4.40, 3.80). Sol in alcohol, benzene, chloroform.