<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2568</id>
  <title>T3D2527</title>
  <common-name>Batrachotoxin</common-name>
  <description>Batrachotoxins (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. (L1069). It is the most potent non-peptidal neurotoxin known.</description>
  <cas>23509-16-2</cas>
  <pubchem-id>31958</pubchem-id>
  <chemical-formula>C31H42N2O6</chemical-formula>
  <weight>538.67498</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Injestion or inhalation (smoking). L1810</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Batrachotoxins 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. (L1069)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Batrachotoxins are  found in poison dart frogs (genus Dendrobates and Phyllobates), Melyridae beetles, and certain birds (genus Pitohui and Ifrita). (L1069)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Batrachotoxins affect the peripheral nervous system and heart muscles. (L1069)</health-effects>
  <symptoms>Batrachotoxins interfere with heart conduction, causing arrhythmias, extrasystoles, ventricular fibrillation and other changes which lead to cardiac arrest. (L1069)</symptoms>
  <treatment>While 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. (L1069)</treatment>
  <created-at type="dateTime">2009-07-03T22:19:11Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:39Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Batrachotoxin</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C13750</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Batrachotoxin</stitch-id>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC(OC(=O)C1=C(C)NC=C1C)C1=CCC23OCCN(C)CC12CC(O)C12OC4(O)CCC1(C)C(CC=C32)C4</moldb-smiles>
  <moldb-formula>C31H42N2O6</moldb-formula>
  <moldb-inchi>InChI=1/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</moldb-inchi>
  <moldb-inchikey>InChIKey=ISNYUQWBWALXEY-UHFFFAOYNA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">538.675</moldb-average-mass>
  <moldb-mono-mass type="decimal">538.304287086</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id nil="true"/>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
