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

Veratridine is a steroidal alkaloid neurotoxin derived from the seeds of Schoenocaulon officinale and the rhizome of Veratrum album. It is a colorless, amorphous powder that is soluble in lipid and belongs to the family Liliaceae and genus, Schoenocaulon. Veratridine is known for its ability to cause Na+ channels to stay open during sustained membrane depolarization by abolishing inactivation, which in turn opens voltage-activated calcium channels, increasing intracellular calcium content, and inducing neurotransmitter release.

Uses

Used in Pharmaceutical Research:
VERATRIDINE is used as a research tool for studying the effects of increased membrane sodium permeability on excitable tissues. Its ability to cause Na+ channels to stay open during sustained membrane depolarization makes it a valuable compound for understanding the mechanisms of ion channel function and dysfunction in various diseases and conditions.
Used in Neurophysiology:
VERATRIDINE is used as a neurotoxin in neurophysiological experiments to investigate the role of sodium channels in nerve cell function and neurotransmission. By increasing intracellular calcium content and inducing neurotransmitter release, it helps researchers understand the complex interactions between ion channels and neurotransmitters in the nervous system.
Used in Drug Development:
VERATRIDINE is used as a starting point for the development of new drugs targeting sodium channels and related neurological disorders. Its unique properties and effects on ion channels make it a promising candidate for the development of novel therapeutic agents for conditions such as epilepsy, chronic pain, and certain neurodegenerative diseases.
Used in Toxicology:
VERATRIDINE is used as a reference compound in toxicological studies to evaluate the potential hazards and risks associated with exposure to alkaloid neurotoxins. Understanding the toxic effects of VERATRIDINE can help in the development of safety guidelines and protocols for handling and using similar compounds in research and pharmaceutical applications.
Used in Analytical Chemistry:
VERATRIDINE is used as a reference substance in analytical chemistry for the development and validation of methods for the detection and quantification of alkaloid neurotoxins in various samples, including plant extracts, pharmaceutical products, and environmental samples. Its unique chemical properties make it an ideal candidate for method development and optimization.

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

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