Veratridine

Veratridine
Names
Other names
(3β,4β,16β)-4,12,14,16,17,20-Hexahydroxy-4,9-epoxycevan-3yl 3,4-dimethoxybenzoate
3-Veratroylveracevine
Identifiers
71-62-5 YesY
3D model (Jmol) Interactive image
ChEMBL ChEMBL451227 N
ChemSpider 5290571 N
ECHA InfoCard 100.000.690
2626
PubChem 6914694
Properties
C36H51NO11
Molar mass 673.80 g·mol−1
Melting point 160 to 180 °C (320 to 356 °F; 433 to 453 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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 abolishing inactivation of 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.

References

  1. ↑ W. A. Catterall (1975). "Activation of the action potential Na+ ionophore of cultured neuroblastoma cells by veratridine and batrachotoxin" (pdf). 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). "Chapter 2 Steroid Alkaloids: The Veratrum Group". In R. H. F. Manske. The Alkaloids: Chemistry and Physiology. 10. New York: Academic Press. pp. 193–285. doi:10.1016/S1876-0813(08)60254-7. ISBN 978-0-12-469510-8.
  4. ↑ V. V. Krishnamurthy; 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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