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

pka

9.54(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 System

Veratridine (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

F 

10

HazardClass 

6.1(a)

PackingGroup 

II

Hazardous Substances Data

71-62-5(Hazardous Substances Data)

Toxicity

LD50 in mice (mg/kg): 1.35 i.p. (Swiss, Bauer); 0.42 i.v. (Krayer); 6.3 s.c. (Tanaka)

MSDS

• Language:English Provider:SigmaAldrich

VERATRIDINE Usage And Synthesis

Description

This 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]²²_D + 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.

Uses

Veratridine 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.

Definition

ChEBI: Veratridine is a steroid. It has a role as a sodium channel modulator. It is functionally related to a cevane.

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.

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.

storage

-20°C

Purification Methods

It 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.]

References

Merck., 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(71-62-5)Related Product Information

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