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 Y
3D model (Jmol)	Interactive image
ChemSpider	5290571 N
ECHA InfoCard	100.000.690
IUPHAR/BPS	2626
PubChem CID	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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (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.

Isolated from seeds of Schoenocaulon officinale, and from rhizomes of Veratrum album.

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.

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