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
CAS Number	71-62-5
ChEMBL	ChEMBL451227
ChemSpider	5290571
IUPHAR/BPS	2626
Jmol interactive 3D	Image
PubChem	6914694
InChI InChI=1S/C36H51NO11/c1-19-6-11-26-31(3,40)35(43)25(17-37(26)16-19)33(42)18-34-24(32(33,41)15-27(35)38)10-9-23-30(34,2)13-12-28(36(23,44)48-34)47-29(39)20-7-8-21(45-4)22(14-20)46-5/h7-8,14,19,23-28,38,40-44H,6,9-13,15-18H2,1-5H3/t19-,23-,24-,25-,26-,27-,28-,30-,31+,32+,33+,34+,35-,36-/m0/s1 Key: FVECELJHCSPHKY-YFUMOZOISA-N InChI=1/C36H51NO11/c1-19-6-11-26-31(3,40)35(43)25(17-37(26)16-19)33(42)18-34-24(32(33,41)15-27(35)38)10-9-23-30(34,2)13-12-28(36(23,44)48-34)47-29(39)20-7-8-21(45-4)22(14-20)46-5/h7-8,14,19,23-28,38,40-44H,6,9-13,15-18H2,1-5H3/t19-,23-,24-,25-,26-,27-,28-,30-,31+,32+,33+,34+,35-,36-/m0/s1 Key: FVECELJHCSPHKY-YFUMOZOIBJ
SMILES 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
Properties
Chemical formula	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.