Veratridine

From Wikipedia, the free encyclopedia
  (Redirected from Veratrine)
Jump to: navigation, search
Veratridine
Veratridine structure.png
Identifiers
CAS number 71-62-5 YesY
PubChem 6914694
ChemSpider 5290571 N
ChEMBL CHEMBL451227 N
IUPHAR ligand 2626
Jmol-3D images 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)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
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[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]

  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.