Veratridine
| Veratridine | |
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Other names
(3β,4β,16β)-4,12,14,16,17,20-Hexahydroxy-4,9-epoxycevan-3yl 3,4-dimethoxybenzoate |
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| Identifiers | |
| CAS number | 71-62-5  |
| PubChem | 6914694 |
| ChemSpider | 5290571  |
| ChEMBL | CHEMBL451227 |
| IUPHAR ligand | 2626 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C36H51NO11 |
| Molar mass | 673.79 g mol−1 |
| Melting point |
160-180 °C, 433-453 K, 320-356 °F |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Veratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by activating sodium ion channels.[1] It is primarily obtained from the herb Veratrum and sabadilla seeds. It binds to intramembrane receptor site 2 and increases intracellular Ca2+ concentration. It acts by preferentially binding to activated Na+ channels causing persistent activation that leads to increased nerve excitability.
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Isolation [edit]
Isolated from seeds of Schoenocaulon officinale, and from rhizomes of Veratrum album.[2]
Chemistry [edit]
Veratridine is a derivative, the 3-veratroate ester, of veracevine, which belongs to the class of C-nor-D-homosteroidal alkaloids. The molecular structure and stereochemistry of this and related alkaloids were only established after decades of chemical investigations.[3] The structure of veratridine has been confirmed by NMR spectroscopy[4] and X-ray crystallography.[5]
Obsolete use [edit]
It is used in ointments for the treatment of neuralgia and rheumatoid pain.[citation needed]
References [edit]
- ^ W. A. Catterall (1975). "Activation of the action potential Na+ ionophore of cultured neuroblastoma cells by veratridine and batrachotoxin". J. Biol. Chem. 250 (11): 4053–4059. PMID 1168643.
- ^ The Merck Index, 10th Ed. (1983), p.1422, Rahway: Merck & Co.
- ^ S. M. Kupchan (1968). In The Alkaloids: Chemistry and Physiology, Vol. 10 (R. H. F. Manske, Ed.), pp.193-285, New York: Academic Press.
- ^ V. V. Krishnamurthy and J. E. Casida (1988). "Complete spectral assignments of cevadine and veratridine by 2D NMR techniques". Magn. Reson. Chem. 26 (11): 980–989. doi:10.1002/mrc.1260261109.
- ^ P. W. Codding (1983). "Structural studies of sodium channel neurotoxins. 2. Crystal structure and absolute configuration of veratridine perchlorate". J. Am. Chem. Soc. 105 (10): 3172–3176. doi:10.1021/ja00348a035.
