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]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.
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.
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)
