3D model (JSmol)
|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).
|what is ?)(|
Veratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by preventing the inactivation of sodium ion channels. It is primarily obtained from plants of the genuses Veratrum and Schoenocaulon. 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.
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. The structure of veratridine has been confirmed by NMR spectroscopy and X-ray crystallography.
- 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.
- The Merck Index, 10th Ed. (1983), p.1422, Rahway: Merck & Co.
- 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.
- 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.
- 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.