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VERATRIDINE

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CAS:71-62-5
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VERATRIDINE Basic information
Product Name:VERATRIDINE
Synonyms:3-VERATROYLVERACEVINE;,4alpha,16beta)-;4,9-epoxycevane-3,4,12,14,16,17,20-heptol3-(3,4-dimethoxybenzoate);cevane-3,4,12,14,16,17,20-heptol,4,9-epoxy-,3-(3,4-dimethoxybenzoate),(3beta;cevane-3-beta,4-alpha,12,14,16-beta,17,20-heptol,4,9-epoxy-,3-(3,4-dimethox;veratrine(amorphous);ybenzoate);4,9-epoxycevane-3beta,4alpha,12,14,16beta,17,20-heptol 3-veratrate
CAS:71-62-5
MF:C36H51NO11
MW:673.79
EINECS:200-758-4
Product Categories:Ion Channels;Alkaloids
Mol File:71-62-5.mol
VERATRIDINE Structure
VERATRIDINE Chemical Properties
Melting point 180℃
alpha D20 +8.0° (ethanol)
Boiling point 689.74°C (rough estimate)
density 1.45±0.1 g/cm3 (20 ºC 760 Torr)
refractive index 1.6630 (estimate)
storage temp. -20°C
solubility ethanol: 50 mg/mL
form powder
pka9.54(at 25℃)
color white to off-white
Merck 13,10016
BRN 78875
Stability:Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
EPA Substance Registry SystemVeratridine (71-62-5)
Safety Information
Hazard Codes T+
Risk Statements 26/27/28-36/37/38-62-52/53-48/20
Safety Statements 26-36/37/39-45-61-36/37-28
RIDADR UN 1544 6.1/PG 1
WGK Germany 2
RTECS YX5600000
10
HazardClass 6.1(a)
PackingGroup II
Hazardous Substances Data71-62-5(Hazardous Substances Data)
ToxicityLD50 in mice (mg/kg): 1.35 i.p. (Swiss, Bauer); 0.42 i.v. (Krayer); 6.3 s.c. (Tanaka)
MSDS Information
ProviderLanguage
SigmaAldrich English
VERATRIDINE Usage And Synthesis
DescriptionThis steroidal alkaloid from Veratrum viride was given this name by Bosetti. It is almost certainly identical with the amorphous veratrine isolated by Schmidt and Koppen, Merck, and Wright and Luff. The base is a colourless, amorphous powder which melts over a wide range. It has [α]22D + 8.0° (EtOH) and yields a sulphate nonahydrate which forms colourless silky needles that resinify in air. The nitrate is only sparingly soluble in H2O. The solution of the alkaloid in H2SO4 becomes orange-red and eventually crimson with a blue fluorescence while that in HCI is colourless. Alkaline hydrolysis furnishes veratric acid and cevine.
UsesVeratridine causes Na+ channels to stay open during a sustained membrane depolarization by abolishing 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.
DefinitionChEBI: Veratridine is a steroid. It has a role as a sodium channel modulator. It is functionally related to a cevane.
General DescriptionVeratridine 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.
Biochem/physiol ActionsOpens 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.
storage-20°C
Purification MethodsIt is an alkaloid neurotoxin which prevents inactivation of Na+ channels. Its solubility in EtOH is ~5%; and it separates as a pale yellow powder from an ethanolic solution on addition of Et2O. It forms nitrate, sulfate and perchlorate salts. [McKinney et al. Anal Biochem 153 33 1986, Beilstein 21 V/13 709.]
ReferencesMerck., Annalen, 95, 200 (1855)
Schmidt, Koppen., Ber., 9, 1115 (1876)
Wright, Luff.,J. Chem. Soc., 35, 421 (1879)
Bosetti., Arch. Pharm., 221,82 (1883)
Blount., Chem. Zeit., 26,334 (1902)
VERATRIDINE Preparation Products And Raw materials
Tag:VERATRIDINE(71-62-5) Related Product Information
Verteporfin >=94% (HPLC) 2,5-Dimethyl-2,5-hexanediol 1,4-Cyclohexanedimethanol L-Menthol STEARYLAMINE ACETATE Isopropylparaben Pinacol Ethyl 3,4-dihydroxybenzoate N-ETHYL-4-HYDROXYPIPERIDINE VERATRIDINE PERHYDROFLUORENE 4-Hydroxy-3-methylpiperidine ETHYL 3,4-DIMETHOXYBENZOATE 1-Piperidinepropanol N, N-DIMETHYLOCTADECYLAMINE ACETATE VERATRIDINE(RG) VERATRINE 3-(1-METHYL-PIPERIDIN-4-YL)-PROPAN-1-OL