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V5754

Sigma-Aldrich

Veratridine

≥90% (HPLC), powder, Na+ channel opener

Synonym(s):

3-Veratroylveracevine, Veracevine veratrate

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About This Item

Empirical Formula (Hill Notation):
C36H51NO11
CAS Number:
71-62-5
Molecular Weight:
673.79
Beilstein/REAXYS Number:
78875
EC Number:
200-758-4
MDL number:
MFCD00082515
UNSPSC Code:
12352200
PubChem Substance ID:
24900756
NACRES:
NA.77

product name

Veratridine, ≥90% (HPLC), powder

Quality Level

100

assay

≥90% (HPLC)

form

powder

color

white to off-white

solubility

ethanol: 50 mg/mL

storage temp.

−20°C

SMILES string

COc1ccc(cc1OC)C(=O)OC2CC[C@@]3(C)C4CCC5[C@]6(O)C[C@H](O)[C@@]7(O)C(CN8CC(C)CCC8[C@@]7(C)O)[C@]6(O)C[C@]35O[C@]24O

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

InChI key

FVECELJHCSPHKY-FCSYLLAHSA-N

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General description

Veratridine is one of several alkaloids isolated from the seeds of Schoenocaulon officinale and from the rhizome of Veratrum album. The crude extract is called veratrine or sabadilla and contains cevadine, veratridine, cevadilline, sabadine and cevine. It is a neurotoxin, which belongs to the family Liliaceae and genus, Schoenocaulon. Veratridine is soluble in lipid.

Application

Veratridine has been used:
  • to record the veratridine-dependent increase in the late Na+ current using a HEK293 cell line stably transfected with human Na v1.5 24(4) to measure the ranolazine-induced inhibition of basal and veratridine-activated I Na late
  • to assess the effects of veratridine on action potentials (APs) in hiPSC-cardiomyocyte preparations externally paced in current-clamp mode
  • to study the inhibitory effects of veratridine on hERG1 current in stably transfected HEK293 cells
  • to treat neuroblastoma 2-a cells to improve sensitivity for N2a assay

Biochem/physiol Actions

Opens voltage-dependent Na+ channels and prevents their inactivation. This, in turn, opens voltage-activated calcium channels, thus increasing intracellular calcium content and inducing neurotransmitter release. Alkaloid neurotoxin which depolarizes excitable tissue; used to increase membrane sodium permeability. Veratridine is cytotoxic to chromaffin cells in vitro.
Veratridine has been used as an insecticide, acting as a paralytic agent with higher toxicity to insects than to mammals.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 1 Inhalation - Acute Tox. 1 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Repr. 2 - Skin Irrit. 2 - STOT RE 2 Inhalation - STOT SE 3

target_organs

Nervous system, Respiratory system

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R Maroto et al.
European journal of pharmacology, 270(4), 331-339 (1994-08-03)
Exposure of bovine chromaffin cells to 30 microM veratridine for 24 h led to 70-80% cell death as reflected by phase contrast microscopy, trypan blue exclusion, lactate dehydrogenase (LDH) release and cell catecholamine contents. Na+ deprivation, Ca2+ deletion or tetrodotoxin
Silmara R Sousa et al.
PloS one, 12(9), e0182848-e0182848 (2017-09-08)
Spider venoms are rich sources of peptidic ion channel modulators with important therapeutical potential. We screened a panel of 60 spider venoms to find modulators of ion channels involved in pain transmission. We isolated, synthesized and pharmacologically characterized Cd1a, a
M Neus Fullana et al.
Glia, 67(6), 1122-1137 (2019-01-13)
Elevation of energy metabolism and disturbance of astrocyte number/function in the ventral anterior cingulate cortex (vACC) contributes to the pathophysiology of major depressive disorder (MDD). Functional hyperactivity of vACC may result from reduced astrocytic glutamate uptake and increased neuronal excitation.
Veratridine modifies the gating of human voltage-gated sodium channel Nav1.7
Zhang X, et al.
Acta Pharmacologica Sinica, 39, 1716-1724 (2018)
Irina Vetter et al.
Biochemical pharmacology, 83(11), 1562-1571 (2012-03-14)
The human neuroblastoma cell line SH-SY5Y is a potentially useful model for the identification and characterisation of Na(v) modulators, but little is known about the pharmacology of their endogenously expressed Na(v)s. The aim of this study was to determine the
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