Structure via PubChem · Public domain (PubChem)
veratridine
Sign in to savethumb|Unlike the typical 6-6-6-5 steroid ring backbone (1), veratridine displays a 6-6-5-6 arrangement (2).Veratridine is a steroidal alkaloid found in plants related to lilies, specifically the genera Veratrum and Schoenocaulon. 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. Veratridine increases nerve excitability and intracellular Ca2+ concentrations.
Chemical data
- Formula
- C36H51NO11
- Molecular weight
- 673.8 g/mol
- IUPAC name
- [(1R,2S,6S,9S,10R,11S,12S,14R,15S,18S,19S,22S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] 3,4-dimethoxybenzoate
- SMILES
- C[C@H]1CC[C@H]2[C@@]([C@]3([C@H](C[C@]4([C@@H]5CC[C@H]6[C@]7([C@]5(C[C@]4([C@@H]3CN2C1)O)O[C@@]6([C@H](CC7)OC(=O)C8=CC(=C(C=C8)OC)OC)O)C)O)O)O)(C)O
- InChIKey
- FVECELJHCSPHKY-YFUMOZOISA-N
- XLogP
- 1
- Polar surface area
- 179 Ų
- H-bond donors
- 6
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,675 papers- Kinetics of veratridine action on Na channels of skeletal muscle.The Journal of general physiology · 1986
- Effects of veratridine on sodium currents and fluxes.Reviews of physiology, biochemistry and pharmacology · 1998
- Veratridine-induced intoxication: an in vitro model for the characterization of anti-ischemic compounds?Journal of basic and clinical physiology and pharmacology · 1992
- Veratridine-sensitive Na(+) channels regulate human sperm fertilization capacity.Life sciences · 2018
- Veratridine modifies the gating of human voltage-gated sodium channel Nav1.7.Acta pharmacologica Sinica · 2018
via PubMed
Wikidata facts
- Mass
- 673.346211452
- Has use
- insecticide
Show 6 more facts
- found in taxon
- Artemisia maritima
- chemical formula
- C₃₆H₅₁NO₁₁
- canonical SMILES
- CC1CCC2C(C3(C(CC4(C5CCC6C7(C5(CC4(C3CN2C1)O)OC6(C(CC7)OC(=O)C8=CC(=C(C=C8)OC)OC)O)C)O)O)O)(C)O
- Commons category
- Veratridine
- isomeric SMILES
- C[C@H]1CC[C@H]2[C@@]([C@]3([C@H](C[C@]4([C@@H]5CC[C@H]6[C@]7([C@]5(C[C@]4([C@@H]3CN2C1)O)O[C@@]6([C@H](CC7)OC(=O)C8=CC(=C(C=C8)OC)OC)O)C)O)O)O)(C)O
- subject has role
- neurotoxin
via Wikidata · CC0
~6 min read
Encyclopedic overview
6 sectionsContents
- Isolation
- Chemistry
- Structure
- Solubility
- Mechanism of action and applications
- References
thumb|Unlike the typical 6-6-6-5 steroid ring backbone (1), veratridine displays a 6-6-5-6 arrangement (2).Veratridine is a steroidal alkaloid found in plants related to lilies, specifically the genera Veratrum and Schoenocaulon. 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. Veratridine increases nerve excitability and intracellular Ca2+ concentrations.
==Isolation== Veratridine has been isolated from the seeds of Schoenocaulon officinale and from the rhizomes of Veratrum album. Like the other steroidal alkaloids found in these plants and similar ones in the Melanthiaceae family, it is present as part of a glycosidal combination, bonded to carbohydrate moieties.
Excerpted from Wikipedia’s “veratridine” article, available under the CC BY-SA 4.0 licence.