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Veratridine

Veratridine structure

Veratridine 

structure
  • CAS No:

    71-62-5

  • Formula:

    C36H51NO11

  • Chemical Name:

    Veratridine

  • Synonyms:

    Cevane-3,4,12,14,16,17,20-heptol,4,9-epoxy-,3-(3,4-dimethoxybenzoate),(3β,4α,16β)-;Veratridine;3-Veratroylveracevine;Veracevine,veratrate;NSC 7524;25902-60-7

  • Categories:

    Natural Products  >  Alkaloids

Description

Veratridine (3-Veratroylveracevine), a alkaloid derived from plants in the family Liliaceae, is a sodium channel agonist. Veratridine inhibits the peak current of Nav1.7, with an IC50 of 18.39 µM.


A benzoate-cevane found in VERATRUM and Schoenocaulon. It activates SODIUM CHANNELS to stay open longer than normal.

Veratridine Basic Attributes

673.79

673.79

200-758-4

DTXSID2058467

YELLOWISH-WHITE, AMORPHOUS POWDER

2929101000

Characteristics

178.61000

1.29390

white to off-white powder

1.45 g/cm3

180 °C

814.5ºC at 760 mmHg

446.4ºC

1.663

ethanol: 50 mg/mL

−20°C

Abdominal cavity-rat LD50: 3.5 mg/kg; abdominal cavity-mouse LD50: 1.35 mg/kg

Combustible, the fire emits spicy nitrogen oxides and stimulates smoke

D20 +8.0° (ethanol)

RETAINS WATER TENACIOUSLY

Safety Information

II

6.1(a)

UN 1544 6.1/PG 1

2

26/27/28-36/37/38-62-52/53-48/20

26-36/37/39-45-61-36/37-28

YX5600000

T+

Treasury is low temperature, ventilated, dry; stored separately from food raw materials

P260-P262-P280-P301 + P310 + P330-P302 + P352 + P310-P304 + P340 + P310-P403 + P233

H300 + H310 + H330-H315-H319-H335-H361-H373-H412

A REVIEW, WITH 37 REFERENCES, OF RELEASE OF CATECHOLAMINE BY VERATRIDINE & SCORPION VENOM & ALTERATIONS IN EXTRACELLULAR K & NA.[PATON DM; RELEASE INDUCED BY ALTERATIONS IN EXTRACELLULAR POTASSIUM AND SODIUM AND BY VERATRIDINE AND SCORPION VENOM; RELEASE CATECHOLAMINES ADRENERGIC NEURONS 323 (1979)]|REVIEW OF NEURONAL SODIUM CHANNEL REGULATION BY NEUROTOXINS, INCLUDING VERATRIDINE.[KRUEGER BK, BLAUSTEIN MP; REGULATION OF NEURONAL SODIUM CHANNELS BY NEURO TOXINS; SHAMOO, AD (ED) ANNALS OF THE NEW YORK ACADEMY OF SCIENCES, VOL 358 2ND INTERNATIONAL CONFERENCE ON CARRIERS AND CHANNELS IN BIOLOGICAL SYSTEMS: TRANSPORT PROTEINS; NEW YORK, NY, USA FEB 4-6, 348 (1980)]|REVIEW OF NEUROTOXINS, INCLUDING VERATRIDINE, THAT ACT ON VOLTAGE SENSITIVE SODIUM CHANNELS IN EXCITABLE MEMBRANES.[CATTERALL NA; NEURO TOXINS THAT ACT ON VOLTAGE SENSITIVE SODIUM CHANNELS IN EXCITABLE MEMBRANES; GEROGE R, OKUN R (ED). ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY 20, 15 (1980)]

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P262, P264, P270, P271, P280, P281, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 129 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

SLIGHT.

Toxicity

most toxic

THE ACTION OF VERATRIDINE ON THE RESTING MEMBRANE POTENTIAL OF INTACT CRAYFISH (PROCAMBARUS CLARKI) AXONS IN THE PRESENCE OF DIFFERENT EXTRACELLULAR ALKALINE-EARTH CATIONS WERE STUDIED USING INTRACELLULAR MICROELECTRODES. AT EXTRACELLULAR PH VALUES OF 7, 6, & 5, THE APPARENT BINDING SEQUENCE WAS CA2+ GREATER THAN OR EQUAL TO SR2+ MORE THAN MG2+ APPROX BA2+.

Drug Information

HAS BEEN TESTED IN MYASTHENIA GRAVIS TO INCREASE MUSCLE RESPONSE TO GIVEN MOTOR NEURON STIMULATION.|USED EXPERIMENTALLY TO ALTER SODIUM CHANNEL KINETICS /PRC: IN EXCITABLE MEMBRANES/

DATA GIVEN FOR LIPID SOLUBILITY, BINDING TO HUMAN ALBUMIN, & URINARY EXCRETION AFTER ORAL ADMIN TO HUMANS. STRUCTURE-ACTIVITY CORRELATIONS ARE DISCUSSED WITH RESPECT TO LIPID SOLUBILITY & PHARMACOLOGICAL PROPERTIES.

THE EFFECTS OF VERATRIDINE ON EXCITABLE TISSUES ARE PREDICTABLE, BASED ON ITS ABILITY TO ENHANCE SODIUM PERMEABILITY. EFFECTS INCLUDE, AMONG OTHERS, RELEASE OF NEUROTRANSMITTERS, HORMONES, DRUGS TAKEN UP BY NERVE ENDINGS, ETC.

Veratridine

Veratridine Use and Manufacturing

Methods of Manufacturing

FROM SEED OF SCHOENOCAULON OFFICINALE (SCHLECHT & CHAM) A GRAY & ALSO FROM RHIZOME OF VERATRUM ALBUM L LILIACEAE. ...ISOLATED FROM COMMERCIAL VERATRINE AS SPARINGLY SOL NITRATE: BLOUNT, J CHEM SOC 1935, 122; VEJDELEK ET AL, CHEM LISTY 50, 603 (1956); COLL CZECH CHEM COMMUN 22, 98 (1957).

COMPONENT OF SABADILLA (USED AS AN INSECTICIDE)

Computed Properties

Molecular Weight:673.8
XLogP3:1
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:5
Exact Mass:673.34621144
Monoisotopic Mass:673.34621144
Topological Polar Surface Area:179
Heavy Atom Count:48
Complexity:1340
Undefined Atom Stereocenter Count:14
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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