| Identification | Back Directory | [Name]
VERATRIDINE | [CAS]
71-62-5 | [Synonyms]
NSC 7524
Veratrdine
ybenzoate)
VERATRIDINE
,4alpha,16beta)-
Veratridine, >=98%
veratrine(amorphous)
3-VERATROYLVERACEVINE
VERATRIDINE FREE BASE
Veracevine, veratrate
1,2,4-triazolo[4,3-a]pyridin-3-ol
O3-(3,4-Dimethoxybenzoyl)veracevine
Veratridine - CAS 71-62-5 - Calbiochem
4α,9-Epoxy-3β-veratroyloxy-5β-cevan-4β,12,14,16β,17,20-hexaol
4,9-epoxycevane-3beta,4alpha,12,14,16beta,17,20-heptol 3-veratrate
4,9-epoxycevane-3,4,12,14,16,17,20-heptol3-(3,4-dimethoxybenzoate)
cevane-3-beta,4-alpha,12,14,16-beta,17,20-heptol,4,9-epoxy-,3-(3,4-dimethox
cevane-3,4,12,14,16,17,20-heptol,4,9-epoxy-,3-(3,4-dimethoxybenzoate),(3beta
Cevane-3,4,12,14,16,17,20-heptol, 4,9-epoxy-, 3-(3,4-dimethoxybenzoate), (3β,4α,16β)- | [EINECS(EC#)]
200-758-4 | [Molecular Formula]
C36H51NO11 | [MDL Number]
MFCD00082515 | [MOL File]
71-62-5.mol | [Molecular Weight]
673.79 |
| Chemical Properties | Back Directory | [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. | [InChIKey]
FVECELJHCSPHKY-QYUNFSACNA-N | [SMILES]
[C@]123O[C@]4(O)C(OC(=O)C5=CC=C(OC)C(OC)=C5)CCC1(C)C4CCC2[C@]1([C@](O)(C2CN4C(CCC(C)C4)[C@](O)(C)[C@@]2(O)[C@@H](O)C1)C3)O |&1:0,2,26,27,38,41,43,r| | [EPA Substance Registry System]
Veratridine (71-62-5) |
| Hazard Information | Back Directory | [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. | [storage]
Store at -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) |
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