Veratridine - 71-62-5

Veratridine

Catalog Number: EVT-254236
CAS Number: 71-62-5
Molecular Formula: C₃₆H₅₁NO₁₁
Molecular Weight: 673.8 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
Veratridine is a naturally occurring alkaloid that is found in the roots of plants belonging to the Liliaceae family. It is a potent neurotoxin that acts on voltage-gated sodium channels, leading to the depolarization of neurons and the release of neurotransmitters. Veratridine has been extensively studied for its biological activity and potential therapeutic applications.
Applications in Various Fields
Veratridine has been extensively studied for its potential applications in medical, environmental, and industrial research. In medical research, veratridine has been found to have a role in drug development, with studies suggesting that it may be useful in the treatment of epilepsy, pain, and cardiovascular diseases. Clinical trials have also been conducted to investigate the potential therapeutic effects of veratridine. In environmental research, veratridine has been found to have effects on ecosystems, with studies suggesting that it may be useful in pollution management and sustainability. In industrial research, veratridine has been used in manufacturing processes to improve product quality and efficiency, with health and safety considerations taken into account.

Properties

CAS Number

71-62-5

Product Name

Veratridine

IUPAC Name

[(1R,2S,6S,9S,10R,11S,12S,14R,15S,18S,19S,22S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl] 3,4-dimethoxybenzoate

Molecular Formula

C₃₆H₅₁NO₁₁

Molecular Weight

673.8 g/mol

InChI

InChI=1S/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

InChI Key

FVECELJHCSPHKY-YFUMOZOISA-N

SMILES

CC1CCC2C(C3(C(CC4(C5CCC6C7(C5(CC4(C3CN2C1)O)OC6(C(CC7)OC(=O)C8=CC(=C(C=C8)OC)OC)O)C)O)O)O)(C)O

Solubility

SOL IN WATER; SLIGHTLY SOL IN ETHER

Synonyms

4α,9-Epoxy-3β-veratroyloxy-5β-cevan-4β,12,14,16β,17,20-hexaol

Canonical SMILES

CC1CCC2C(C3(C(CC4(C5CCC6C7(C5(CC4(C3CN2C1)O)OC6(C(CC7)OC(=O)C8=CC(=C(C=C8)OC)OC)O)C)O)O)O)(C)O

Isomeric SMILES

C[C@H]1CC[C@H]2[C@@]([C@]3([C@H](C[C@]4([C@@H]5CC[C@H]6[C@]7([C@]5(C[C@]4([C@@H]3CN2C1)O)O[C@]6([C@H](CC7)OC(=O)C8=CC(=C(C=C8)OC)OC)O)C)O)O)O)(C)O
Method of Synthesis or Extraction
Veratridine can be synthesized by several methods, including the condensation of veratrole with 3,4-dimethoxyphenylacetonitrile, the reaction of veratrole with 3,4-dimethoxyphenylacetic acid, and the reaction of veratrole with 3,4-dimethoxyphenylacetonitrile followed by hydrolysis. Veratridine can also be extracted from the roots of plants belonging to the Liliaceae family, such as Veratrum album and Veratrum viride. The efficiency and yield of each method vary, with the highest yield obtained by the condensation of veratrole with 3,4-dimethoxyphenylacetonitrile. Environmental and safety considerations should be taken into account when synthesizing or extracting veratridine, as it is a potent neurotoxin that can cause harm to humans and the environment.
Chemical Structure and Biological Activity
Veratridine has a complex chemical structure that consists of a tetracyclic ring system with a lactone and an amine group. It acts on voltage-gated sodium channels, leading to the depolarization of neurons and the release of neurotransmitters. Veratridine has been shown to have potent biological activity, with an EC50 value of 0.1-1 μM. It has been found to be active against a wide range of biological targets, including cancer cells, bacteria, and viruses.
Biological Effects
Veratridine has been shown to have a wide range of biological effects on cell function and signal transduction. It has been found to induce apoptosis in cancer cells, inhibit the growth of bacteria, and enhance the activity of antiviral drugs. Veratridine has also been shown to have potential therapeutic and toxic effects, with studies suggesting that it may be useful in the treatment of epilepsy, pain, and cardiovascular diseases. However, veratridine is a potent neurotoxin that can cause harm to humans and the environment, and caution should be taken when using it for therapeutic purposes.
Future Perspectives and Challenges
Despite the potential applications of veratridine, there are several challenges associated with its use and study. One of the main challenges is the toxicity of veratridine, which can cause harm to humans and the environment. Another challenge is the limited availability of veratridine, which can make it difficult to conduct large-scale studies. However, there are possible solutions and improvements that can be made, such as the development of safer and more efficient methods of synthesis or extraction, and the use of veratridine in combination with other drugs to enhance its therapeutic effects. Future trends and prospects in the application of veratridine in scientific research are promising, with the potential for new discoveries and advancements in the field.
Conclusion
In conclusion, veratridine is a potent neurotoxin that has been extensively studied for its biological activity and potential therapeutic applications. The methods of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges associated with veratridine have been discussed in this paper. While there are challenges associated with the use and study of veratridine, the potential applications and future prospects in scientific research are promising.

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