Batrachotoxin (CHEM002069)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-03 22:19:11 UTC
Update Date2016-11-09 01:08:40 UTC
Accession NumberCHEM002069
Identification
Common NameBatrachotoxin
ClassSmall Molecule
DescriptionBatrachotoxins (BTX) are extremely potent cardiotoxic and neurotoxic steroidal alkaloids found in poison dart frogs (genus Dendrobates and Phyllobates), Melyridae beetles, and certain birds (genus Pitohui and Ifrita). They act directly on sodium channels. (1). It is the most potent non-peptidal neurotoxin known.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Animal Toxin
  • Ester
  • Ether
  • Frog/Toad Toxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC31H42N2O6
Average Molecular Mass538.675 g/mol
Monoisotopic Mass538.304 g/mol
CAS Registry Number23509-16-2
IUPAC NameNot Available
Traditional NameNot Available
SMILESCC(OC(=O)C1=C(C)NC=C1C)C1=CCC23OCCN(C)CC12CC(O)C12OC4(O)CCC1(C)C(CC=C32)C4
InChI IdentifierInChI=1S/C31H42N2O6/c1-18-16-32-19(2)25(18)26(35)38-20(3)22-8-9-30-23-7-6-21-14-29(36)11-10-27(21,4)31(23,39-29)24(34)15-28(22,30)17-33(5)12-13-37-30/h7-8,16,20-21,24,32,34,36H,6,9-15,17H2,1-5H3
InChI KeyISNYUQWBWALXEY-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cell surface
  • Extracellular
  • Membrane
  • Membrane Fraction
  • Mitochondrion
  • Nerve Fiber
  • Plasma Membrane
  • Sarcoplasmic Reticulum
  • Synaptic Vesicle
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
AnticonvulsantsNot AvailableNot Available
Vascular smooth muscle contractionNot Availablemap04270
EndocytosisNot Availablemap04144
Antiarrhythmic DrugsNot AvailableNot Available
Cell cycleNot Availablemap04110
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0302390000-95806a83933e485bad91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3715930000-1cd3a85e8d3d3496a7a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-7912000000-4c69959424f897dadfaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2001490000-ee586b0996e270ee7a95Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-8302390000-0573bafbdf0b177deeceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006y-9328200000-a55a34ac2784a1dc5fdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0001690000-3d0d8bddf60c524a9335Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fkm-6802960000-6039b235411c5d81c9ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6y-9007610000-ac37901672847fa49e19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1503090000-d614010212f7e16b1eccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-3402980000-b2e73f3e645c34c63995Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9102200000-c875103e3d7279857eeeSpectrum
Toxicity Profile
Route of ExposureInjestion or inhalation (smoking). L1810
Mechanism of ToxicityBatrachotoxins act on sodium channels by modifying both their ion selectivity and voltage sensitivity. By increasing the permeability of the cell membrane, the cell is depolarized by the influx of sodium. Sodium channels become persistently active at the resting membrane potential and nerve signal transmission to the muscles is blocked. Batrachotoxin also induces a massive release of acetylcholine in nerves and muscles and destroys of synaptic vesicles. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBatrachotoxins are found in poison dart frogs (genus Dendrobates and Phyllobates), Melyridae beetles, and certain birds (genus Pitohui and Ifrita). (1)
Minimum Risk LevelNot Available
Health EffectsBatrachotoxins affect the peripheral nervous system and heart muscles. (1)
SymptomsBatrachotoxins interfere with heart conduction, causing arrhythmias, extrasystoles, ventricular fibrillation and other changes which lead to cardiac arrest. (1)
TreatmentWhile it is not an antidote to batrachotocins, the membrane depolarization can be prevented or reversed by either tetrodotoxin, which is a non-competitive inhibitor, or saxitoxin. These both have effects antagonistic to those of batrachotoxin on sodium flux. Certain anaesthetics may act as receptor antagonists to the action of this alkaloid poison, while other local anaesthetics block its action altogether by acting as competitive antagonists. (1)
Concentrations
Not Available
IdentifiersNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available