Cymarin

Title: Cymarin
CAS Registry Number: 508-77-0
CAS Name: 3b-[(2,6-Dideoxy-3-O-methyl-b-D-ribo-hexopyranosyl)oxy]-5b,14-dihydroxy-19-oxocard-20(22)-enolide
Additional Names: K-strophanthin-a
Trademarks: Alvonal MR (Gecke)
Molecular Formula: C30H44O9
Molecular Weight: 548.66
Percent Composition: C 65.67%, H 8.08%, O 26.24%
Literature 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°. [a]D20 +39.2° (methanol); [a]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).
Melting point: mp 148°
Optical Rotation: [a]D20 +39.2° (methanol); [a]D22 +39.0° (c = 1.7 in chloroform)
Toxicity data: LD50 i.v. in rats: 24.8±1.8 mg/kg (Vogel, Kluge)
Derivative Type: Sesquihydrate
Properties: Hexagonal plates from dil ethanol, mp 184-185°.
Melting point: mp 184-185°
Derivative Type: Monoacetylcymarin
Molecular Formula: C32H46O10
Molecular Weight: 590.70
Percent Composition: C 65.07%, H 7.85%, O 27.09%
Properties: Needles from dil methanol, mp 175-176°. [a]D22 +45.1° (ethanol). Sol in chloroform. Practically insol in water.
Melting point: mp 175-176°
Optical Rotation: [a]D22 +45.1° (ethanol)
Therap-Cat: Cardiotonic.
Keywords: Cardiotonic.
Cymarose Cymene Cymiazole Cymoxanil Cynanchogenin

Cymarin
Cymarine.png
Systematic (IUPAC) name
(3S,5S,8R,10S,13R,14S,17R)-5,14-dihydroxy-3-((2R,4S,5S,6R)-5-hydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yloxy)-13-methyl-17-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
Clinical data
Legal status  ?
Identifiers
CAS number 508-77-0 YesY
ATC code C01AC03
PubChem CID 441853
ChemSpider 390429 N
UNII UK3LS8435E YesY
ChEMBL CHEMBL1651908 YesY
Synonyms Cymarine; K-Strophanthin-α; NSC 7522; Strophantin K; WV 90043a; k-Strophanthin-α
Chemical data
Formula C30H44O9 
Mol. mass 548.665 g/mol
 N (what is this?)  (verify)

Cymarin (or cymarine) is a cardiac glycoside. Apocynum cannabinum used as a source of fiber by Native Americans and Apocynum venetum (Chinese: 羅布麻) used as a herbal tea in China both contain cymarin.[1] Cymarin is a cardiac glycoside and an anti-arrhythmia and cardiotonic agent.[2]