2033. Cevadine

Nomenclature

CAS number: 62-59-9
[3β(Z),4α,16β]-4,9-Epoxycevane-3,4,12,14,16,17,20-heptol 3-(2-methyl-2-butenoate); veratrine.
C32H49NO9; mol wt 591.73.
C 64.95%, H 8.35%, N 2.37%, O 24.33%.

Description and references

From seeds of Schoenocaulon officinale (Schlecht & Cham.) A. Gray (Sabadilla officinarum Brandt), Liliaceae: Poetsch et al., J. Am. Pharm. Assoc. 38, 525 (1949); Ringel, ibid. 45, 433 (1956). Evaluation as insecticide: Ikawa, Link et al., J. Biol. Chem. 159, 517 (1945). Structure: Kupchan, Alfonso, ibid. 49, 242 (1960). Toxicity study: Swiss, Bauer, Proc. Soc. Exp. Biol. Med. 76, 847 (1951). Review: Wintersteiner in Graff, Essays in Biochemistry (Wiley, New York, 1956) pp 308-321.

Chemical structure

Properties

Flat needles from ether, decomp 213-214.5°. [α]D20 +12.8° (c = 3.2 in alc). One gram dissolves in about 15 ml alc or ether; slightly sol in water. LD50 i.p. in mice: 3.5 mg/kg (Swiss, Bauer).

Derivative

Aurichloride.

Properties

Fine yellow needles from alc, dec 190°.

Derivative

Mercurichloride.
C32H49NO9.HCl.HgCl2; mol wt 899.69.
C 42.72%, H 5.60%, N 1.56%, O 16.00%, Cl 11.82%, Hg 22.30%.

Properties

Silvery scales, dec 172°.

Caution

Extremely irritating locally, particularly to mucous membranes. Serious poisoning has resulted from local application. Caution must be used in handling. See also Veratrine (Mixture).