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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/06 14:16:57」(JST)

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Veratridine is a steroid-derived alkaloid from plants in the Liliaceae family that functions as a neurotoxin by abolishing inactivation of sodium ion channels.^[1] It is primarily obtained from the herb Veratrum and sabadilla seeds. It binds to intramembrane receptor site 2 and increases intracellular Ca²⁺ concentration. It acts by preferentially binding to activated Na⁺ channels causing persistent activation that leads to increased nerve excitability.

Isolation

Isolated from seeds of Schoenocaulon officinale, and from rhizomes of Veratrum album.^[2]

Chemistry

Veratridine is a derivative, the 3-veratroate ester, of veracevine, which belongs to the class of C-nor-D-homosteroidal alkaloids. The molecular structure and stereochemistry of this and related alkaloids were only established after decades of chemical investigations.^[3] The structure of veratridine has been confirmed by NMR spectroscopy^[4] and X-ray crystallography.^[5]

Obsolete use

It is used in ointments for the treatment of neuralgia and rheumatoid pain.^{[citation needed]}

References

^ W. A. Catterall (1975). "Activation of the action potential Na⁺ ionophore of cultured neuroblastoma cells by veratridine and batrachotoxin" (pdf). J. Biol. Chem. 250 (11): 4053–4059. PMID 1168643.
^ The Merck Index, 10th Ed. (1983), p.1422, Rahway: Merck & Co.
^ S. M. Kupchan (1968). "Chapter 2 Steroid Alkaloids: The Veratrum Group". In R. H. F. Manske. The Alkaloids: Chemistry and Physiology 10. New York: Academic Press. pp. 193–285. doi:10.1016/S1876-0813(08)60254-7. ISBN 978-0-12-469510-8.
^ V. V. Krishnamurthy; J. E. Casida (1988). "Complete spectral assignments of cevadine and veratridine by 2D NMR techniques". Magn. Reson. Chem. 26 (11): 980–989. doi:10.1002/mrc.1260261109.
^ P. W. Codding (1983). "Structural studies of sodium channel neurotoxins. 2. Crystal structure and absolute configuration of veratridine perchlorate". J. Am. Chem. Soc. 105 (10): 3172–3176. doi:10.1021/ja00348a035.

UpToDate Contents

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1. 小児での潜在的に毒性を持つ植物の摂取による臨床症状および評価 clinical manifestations and evaluation of potentially toxic plant ingestions in children

English Journal

Lacosamide inhibits calcitonin gene-related peptide production and release at trigeminal level in the rat.

Greco MC1, Capuano A2, Navarra P1, Tringali G1.
European journal of pain (London, England).Eur J Pain.2016 Jul;20(6):959-66. doi: 10.1002/ejp.820. Epub 2016 Jan 5.
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PMID 26729049

Gramine derivatives targeting Ca2+ channels and Ser/Thr phosphatases: a new dual strategy for the treatment of neurodenerative diseases.

Lajarín-Cuesta R, Nanclares C, Arranz-Tagarro JA, González-Lafuente L, Arribas RL, Brito MA, Gandia L, de Los Ríos C.
Journal of medicinal chemistry.J Med Chem.2016 Jun 9. [Epub ahead of print]
We describe the synthesis of gramine derivatives and their pharmacological evaluation as multipotent drugs for the treatment of Alzheimer´s disease. An innovative multitarget approach is presented, targeting both voltage-gated Ca2+ channels, classically studied for neurodegenerative diseases, and S
PMID 27280380

Insecticide sensitivity of native chloride and sodium channels in a mosquito cell line.

Jenson LJ1, Anderson TD2, Bloomquist JR3.
Pesticide biochemistry and physiology.Pestic Biochem Physiol.2016 Jun;130:59-64. doi: 10.1016/j.pestbp.2015.11.012. Epub 2015 Nov 28.
The aim of this study was to investigate the utility of cultured Anopheles gambiae Sua1B cells for insecticide screening applications without genetic engineering or other treatments. Sua1B cells were exposed to the known insecticidal compounds lindane and DIDS, which inhibited cell growth at micromo
PMID 27155485

Japanese Journal

Depolarizing stimuli cause persistent and selective loss of orexin in rat hypothalamic slice culture

Peptides 31(6), 1131-1138, 2010-06
NAID 120002469577

Investigating the in vitro metabolism of veratridine : Characterization of metabolites and involved cytochrome P450 isoforms

Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 877(3), 141-148, 2009-01-15
NAID 10028011771

Inhibition by Selenium Compounds of Catecholamine Secretion Due to Inhibition of Ca^<2+> Influx in Cultured Bovine Adrenal Chromaffin Cells

Journal of pharmacological sciences 101(3), 223-229, 2006-07-20
NAID 10018236954

Related Pictures

Veratridine | 71-62-5 | Sodium channel opener Veratridine O Produto Pesticidas PNG Imagem para download gratuito Influence of ATX, DH-ATX, veratridine and PbTx-2 on the stimulation of | Download Veratridine | ABIN1685856 Functional expression of the voltage-gated Na+-channel Nav1.7 is necessary for EGF Index of /Flowers/H/Hellebore(Stinking) Veratridine, Tocris Bioscience 10mg Veratridine-obtained from the seeds of Schoenocaulon officinale- rhizome of Veratrum album

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リンク元	「神経筋接合部」「ベラトリジン」

「神経筋接合部」

Veratridine
Names
	Other names (3β,4β,16β)-4,12,14,16,17,20-Hexahydroxy-4,9-epoxycevan-3yl 3,4-dimethoxybenzoate; 3-Veratroylveracevine
Identifiers
CAS Registry Number	71-62-5
ChEMBL	ChEMBL451227
ChemSpider	5290571
	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 ; Key: FVECELJHCSPHKY-YFUMOZOISA-N ; 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; Key: FVECELJHCSPHKY-YFUMOZOIBJ ;
IUPHAR/BPS	2626
Jmol-3D images	Image
PubChem	6914694
	SMILES O=C(O[C@H]7CC[C@@]1([C@@]65O[C@@]7(O)[C@H]1CC[C@H]6[C@@]2(O)[C@](O)([C@H]4[C@](O)([C@@H](O)C2)[C@@](O)(C)[C@H]3N(C[C@@H](C)CC3)C4)C5)C)c8ccc(OC)c(OC)c8 ;
Properties
Chemical formula	C36H51NO11
Molar mass	673.80 g·mol−1
Melting point	160 to 180 °C (320 to 356 °F; 433 to 453 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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英: neuromuscular junction (K)
同: 神経筋シナプス neuromuscular synapse

神経筋接合部は軸索終末，シナプス間隙，筋細胞膜から構成される。