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Veratridine

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Title: Veratridine  
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Subject: List of MeSH codes (D03), Veracevine, Veratrum, Batrachotoxin, Sodium channel
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Veratridine

Veratridine
Identifiers
CAS number  YesY
PubChem
ChemSpider  N
ChEMBL  N
IUPHAR ligand
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   YesY/N?)

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.

Contents

  • Isolation 1
  • Chemistry 2
  • Obsolete use 3
  • References 4

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). ionophore of cultured neuroblastoma cells by veratridine and batrachotoxin"+"Activation of the action potential Na (pdf). J. Biol. Chem. 250 (11): 4053–4059.  
  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.  
  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.  
  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.  
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