V5754

Sigma-Aldrich

Veratridine

≥90% (HPLC), powder

Sinónimos:
3-Veratroylveracevine, Veracevine veratrate
Empirical Formula (Hill Notation):
C36H51NO11
Número de CAS:
Peso molecular:
673.79
Beilstein/REAXYS Number:
78875
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Quality Level

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

Packaging

25, 100 mg in glass bottle
10 mg in glass insert

Biochem/physiol Actions

Veratridine has been used as an insecticide, acting as a paralytic agent with higher toxicity to insects than to mammals.
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.

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Target Organs

Nervous system, Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 1544PSN1 6.1 / PGI

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

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...
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...
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...
Dharmendra Singh Chauhan et al.
Theriogenology, 90, 210-218 (2017-02-09)
The aim of our study was to characterize the voltage gated sodium channel Na
Hagit Sason et al.
Cerebral cortex (New York, N.Y. : 1991), 27(2), 1573-1587 (2016-01-23)
d-Serine is a co-agonist of NMDA receptors (NMDARs) whose activity is potentially regulated by Asc-1 (SLC7A10), a transporter that displays high affinity for d-serine and glycine. Asc-1 operates as a facilitative transporter and as an antiporter, though the preferred direction...

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