Visnadine

Chemical compound

C04AX24 (WHO)

Identifiers

IUPAC name

(9R,10R)-10-(acetyloxy)-8,8-dimethyl-2-oxo-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-9-yl (2R)-2-methylbutanoate

CAS Number

477-32-7

PubChem CID

442151

ChemSpider

390669

UNII

0RL4V0K263

KEGG

D08735^Y

CompTox Dashboard (EPA)

DTXSID301023583

ECHA InfoCard100.006.833

Chemical and physical dataFormulaC₂₁H₂₄O₇Molar mass388.416 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

CC[C@H](C(=O)O[C@H]1[C@@](OC2=C([C@H]1OC(=O)C)C3=C(C=CC(=O)O3)C=C2)(C)C)C

InChI

InChI=1S/C21H24O7/c1-6-11(2)20(24)27-19-18(25-12(3)22)16-14(28-21(19,4)5)9-7-13-8-10-15(23)26-17(13)16/h7-11,18-19H,6H2,1-5H3/t11-,18-,19-/m1/s1
Key:GVBNSPFBYXGREE-CXWAGAITSA-N

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Visnadine (or visnadin) is a natural vasodilator.^[1] It was first isolated from bishop's weed (Ammi visnaga), a plant indigenous to the Mediterranean region which has been used for centuries in Egypt as a spasmolytic.^[2]

References

^ Durate J, Vallejo I, Pérez-Vizcaino F, Jiménez R, Zarzuelo A, Tamargo J (June 1997). "Effects of visnadine on rat isolated vascular smooth muscles". Planta Medica. 63 (3). Thieme Medical Publishers: 233–6. doi:10.1055/s-2006-957660. PMID 9225605. S2CID 260248811.
^ Smith E, Hosansky N, Bywater WG, van Tamelen EE (1957). "Constitution of Samidin, Dihydrosamidin and Visnadin". J. Am. Chem. Soc. 79 (13): 3534–3540. doi:10.1021/ja01570a062.