2761. Cymarin

Nomenclature

CAS number: 508-77-0
3β-[(2,6-Dideoxy-3-O-methyl-β-d-ribo-hexopyranosyl)oxy]-5β,14-dihydroxy-19-oxocard-20(22)-enolide; K-strophanthin-α; Alvonal MR (G"odecke).
C30H44O9; mol wt 548.66.
C 65.67%, H 8.08%, O 26.24%.

Description and references

A glycoside of cymarose, the aglucon being strophanthidin. Isoln from Strophanthus kombé Oliv., Apocynaceae: Jacobs, Hoffmann, J. Biol. Chem. 67, 609 (1926); Stoll et al., Helv. Chim. Acta 20, 1484 (1937); from Adonis vernalis L., and A. chrysocyathus Hook., Ranunculaceae: Reichstein, Rosenmund, Pharm. Acta Helv. 15, 150 (1940); Pitra, Cekan, Collect. Czech. Chem. Commun. 26, 1551 (1961); Abubakirov, Yamatova, Zh. Obshch. Khim. 31, 2424 (1961); from Pentopetia androsaemifolia Decne., Asclepiadaceae: Wyss et al., Helv. Chim. Acta 43, 664 (1960); from Castilloa elastica Cerv., Moraceae: Adams, Wilkinson, J. Pharm. Pharmacol. 13, 279 (1961). Structure: Kochetkov et al., Dokl. Akad. Nauk SSSR 136, 613 (1961). Toxicity data: V. G. Vogel, E. Kluge, Arzneim.-Forsch. 11, 848 (1961).

Properties

Needles from methanol, mp 148°. [α]D20 +39.2° (methanol); [α]D22 +39.0° (c = 1.7 in chloroform). Sol in methanol, chloroform. Practically insol in water. LD50 i.v. in rats: 24.8±1.8 mg/kg (Vogel, Kluge).

Derivative

Sesquihydrate.

Properties

Hexagonal plates from dil ethanol, mp 184-185°.

Derivative

Monoacetylcymarin.
C32H46O10; mol wt 590.70.
C 65.07%, H 7.85%, O 27.09%.

Properties

Needles from dil methanol, mp 175-176°. [α]D22 +45.1° (ethanol). Sol in chloroform. Practically insol in water.

Therapeutic Category

Cardiotonic.

Keywords

Cardiotonic