2674. Curine

Nomenclature

CAS number: 436-05-5
(13aR,25aR)-2,3,13a,14,15,16,25,25a-Octahydro-18,29-dimethoxy-1,14-dimethyl-13H-4,6:21,24-dietheno-8,12-metheno-1H-pyrido[3′,2′:14,15][1,11]dioxacycloeicosino[2,3,4-ij]isoquinoline-9,19-diol; (1β)-6,6′-dimethoxy-2,2′-dimethyltubocuraran-7′,12′-diol; l-bebeerine.
C36H38N2O6; mol wt 594.70.
C 72.71%, H 6.44%, N 4.71%, O 16.14%.

Description and references

From tubocurare (Chondodendron tomentosum R. & P., Menispermaceae): Boehm, Arch. Pharm. 235, 660 (1897); Sp"ath et al., Ber. 61, 1698 (1928). Structure: Sp"ath, Kuffner, Ber. 67, 55 (1934); Faltis et al., Ber. 69, 1269 (1936); King, J. Chem. Soc. 1939, 1157. Configuration: Bick, Clezy, ibid. 1953, 3893; Hultin, Acta Chem. Scand. 17, 753 (1963). Biosynthetic study: D. S. Bhakuni et al., Tetrahedron 43, 3975 (1987). Ca2+ channel interactions: J. P. Felix et al., Biochemistry 31, 11793 (1992).

Chemical structure

Properties

Efflorescent crystals from methanol. mp 213°; mp 221° in vacuo; four sided prisms from benzene containing one mol benzene, mp 161°. [α]D20 -328° (pyridine). Sol in benzene, chloroform, pyridine.