Veratridine

Veratridine

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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 Y
ChEMBL	ChEMBL451227 N
ChemSpider	5290571 N
IUPHAR/BPS	2626
Jmol 3D model	Interactive 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 N Key: FVECELJHCSPHKY-YFUMOZOISA-N 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)
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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. 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.

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. The structure of veratridine has been confirmed by NMR spectroscopy and X-ray crystallography.

Obsolete use

It is used in ointments for the treatment of neuralgia and rheumatoid pain.