Veratridine

Veratridine
Names
IUPAC name
4β,12,14,16β,17,20-Hexahydroxy-4α,9-epoxycevan-3β-yl 3,4-dimethoxybenzoate
Systematic IUPAC name
(3S,4S,4aS,6aS,6bR,8S,8aS,9R,9aS,12S,15aS,15bR,16aR,16bS)-4,6b,8,8a,9,15b-Hexahydroxy-9,12,16b-trimethyldocosahydro-2H-4,16a-epoxybenzo[4,5]indeno[1,2-h]pyrido[1,2-b]isoquinolin-3-yl 3,4-dimethoxybenzoate
Other names
(3β,4β,16β)-4,12,14,16,17,20-Hexahydroxy-4,9-epoxycevan-3yl 3,4-dimethoxybenzoate
3-Veratroylveracevine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.000.690 Edit this at Wikidata
UNII
  • 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
  • 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
C36H51NO11
Molar mass 673.800 g·mol−1
Melting point 160 to 180 °C (320 to 356 °F; 433 to 453 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Unlike the typical 6-6-6-5 steroid ring backbone (1), veratridine displays a 6-6-5-6 arrangement (2).[1]

Veratridine is a steroidal alkaloid found in plants of the lily family, specifically the genera Veratrum and Schoenocaulon.[1] Upon absorption through the skin or mucous membranes, it acts as a neurotoxin by binding to and preventing the inactivation of voltage-gated sodium ion channels in heart, nerve, and skeletal muscle cell membranes.[2] Veratridine increases nerve excitability and intracellular Ca2+ concentrations.

  1. ^ a b "Steroidal Alkaloids". Pharmacognosy | Plants | herbal | herb | traditional medicine | alternative | Botany. Retrieved 2018-05-02.
  2. ^ Ujváry, István (2010). Hayes' Handbook of Pesticide Toxicology. Elsevier. pp. 119–229. doi:10.1016/b978-0-12-374367-1.00003-3. ISBN 9780123743671.