71-62-5

Basic information

• Product Name: VERATRIDINE
• Synonyms: 3-VERATROYLVERACEVINE;VERATRIDINE;,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)
• CAS NO: 71-62-5
• Molecular Formula: C₃₆H₅₁NO₁₁
• Molecular Weight: 673.79
• EINECS: 200-758-4
• Product Categories: Alkaloids;Ion Channels
• Mol File: 71-62-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 180℃
• Boiling Point: 689.74°C (rough estimate)
• Flash Point: 446.4 °C
• Appearance: white to off-white/powder
• Density: 1.45±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 4.74E-28mmHg at 25°C
• Refractive Index: 1.6630 (estimate)
• Storage Temp.: −20°C
• Solubility: ethanol: 50 mg/mL
• PKA: 9.54(at 25℃)
• 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.
• Merck: 13,10016
• BRN: 78875
• CAS DataBase Reference: VERATRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: VERATRIDINE(71-62-5)
• EPA Substance Registry System: VERATRIDINE(71-62-5)

Safety Data

• Hazard Codes: T+
• 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)

Usage

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.

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)

InChI:InChI=1/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

Synthetic route

3,4-dimethoxybenzoic acid chloride (3535-37-3) + veracevine → veratridine (71-62-5) + O16-veratroyl-veracevine

Conditions	Yield
With pyridine; benzene

methanol (67-56-1) + veratridine (71-62-5) → 4-methoxy veratridine (1028591-36-7)

Conditions	Yield
With cation-exchange resin Dowex 50Wx4 at 55 - 70℃; for 27h;	14%

ethanol (64-17-5) + veratridine (71-62-5) + KOH-solution → Veratric acid (93-07-2) + Cevin (124-98-1)

methanol (67-56-1) + water (7732-18-5) + furan-2,3,5(4H)-trione pyridine (1:1) + veratridine (71-62-5) → 3β,9,12,14,16β,17,20-heptahydroxy-5α-cevan-4-one (559-82-0) + veracevine

Upstream product

• 3535-37-3 3,4-dimethoxybenzoic acid chloride 

Downstream Products

• 1028591-36-7 4-methoxy veratridine 
• 93-07-2 Veratric acid 
• 124-98-1 Cevin