Veratridine

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Veratridine
Other names

(3β,4β,16β)-4,12,14,16,17,20-Hexahydroxy-4,9-epoxycevan-3yl 3,4-dimethoxybenzoate
3-Veratroylveracevine

Identifiers
CAS number 71-62-5 YesY
PubChem 6914694
ChemSpider 5290571 N
ChEMBL CHEMBL451227 N
IUPHAR ligand 2626
Jmol-3D images {{#if:O=C(O[C@H]7CC[C@@]1([C@@]65O[C@@]7(O)[C@H]1CC[C@H]6[C@@]2(O)[C@](O)([C@H]4[C@](O)([C@@H](O)C2)[C@@](O)(C)[C@H]3N(C[C@@H](C)CC3)C4)C5)C)c8ccc(OC)c(OC)c8|Image 1
Properties
Molecular formula C36H51NO11
Molar mass 673.79 g mol−1
Melting point 160 to 180 °C; 320 to 356 °F; 433 to 453 K
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.

Isolation

Isolated from seeds of Schoenocaulon officinale, and from rhizomes of Veratrum album.[2]

Chemistry

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

It is used in ointments for the treatment of neuralgia and rheumatoid pain.[citation needed]

References

  1. ↑ 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. 
  2. ↑ The Merck Index, 10th Ed. (1983), p.1422, Rahway: Merck & Co.
  3. ↑ S. M. Kupchan (1968). In The Alkaloids: Chemistry and Physiology, Vol. 10 (R. H. F. Manske, Ed.), pp.193-285, New York: Academic Press.
  4. ↑ 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. 
  5. ↑ 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. 
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