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Batrachotoxin information


Batrachotoxin
Skeletal formula of batrachotoxin
Skeletal formula of batrachotoxin
Stick model of the batrachotoxin molecule
Stick model of batrachotoxin based on the crystal structure of batrachotoxinin A O-p-bromobenzoate[1]
Ball-and-stick model of the batrachotoxin molecule
Ball-and-stick model of batrachotoxin, as above[1]
Names
Other names
3α,9α-epoxy-14β,18-(2-oxyethyl-N-methylamino)-5β-pregna-7,16-diene-3β,11α,20α-triol 20α-2,4-dimethylpyrrole-3-carboxylate
Identifiers
CAS Number
  • 23509-16-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 10310314 checkY
IUPHAR/BPS
  • 2619
PubChem CID
  • 6324647
UNII
  • TSG6XHX09R checkY
CompTox Dashboard (EPA)
  • DTXSID50893767 Edit this at Wikidata
InChI
  • InChI=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/t20-,21+,24+,27-,28-,29+,30-,31-/m0/s1 checkY
    Key: ISNYUQWBWALXEY-OMIQOYQYSA-N checkY
  • 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/t20-,21+,24+,27-,28-,29+,30-,31-/m0/s1
    Key: ISNYUQWBWALXEY-OMIQOYQYBY
SMILES
  • Cc1c[nH]c(C)c1C(=O)O[C@@H](C)C1=CC[C@@]23OCCN(C)C[C@@]12C[C@@H](O)[C@]12O[C@]4(O)CC[C@@]1(C)[C@H](CC=C23)C4
Properties
Chemical formula
C31H42N2O6
Molar mass 538.685 g·mol−1
Density 1.304 g/mL [2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly toxic
Lethal dose or concentration (LD, LC):
LD50 (median dose)
2 μg/kg
(mouse, sub-cutaneous)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Batrachotoxin (BTX) is an extremely potent cardio- and neurotoxic steroidal alkaloid found in certain species of beetles, birds, and frogs. The name is from the Greek word βάτραχος, bátrachos, 'frog'.[3] Structurally-related chemical compounds are often referred to collectively as batrachotoxins. In certain frogs, this alkaloid is present mostly on the skin. Such frogs are among those used for poisoning darts. Batrachotoxin binds to and irreversibly opens the sodium channels of nerve cells and prevents them from closing, resulting in paralysis and death. No antidote is known.

  1. ^ a b Karle, I. L.; Karle, J. (1969). "The structural formula and crystal structure of the O-p-bromobenzoate derivative of batrachotoxinin A, C31H38NO6Br, a frog venom and steroidal alkaloid". Acta Crystallogr. B. 25 (3): 428–434. Bibcode:1969AcCrB..25..428K. doi:10.1107/S056774086900238X. PMID 5820223. S2CID 28609553.
  2. ^ Daly, J. W.; Journal of the American Chemical Society 1965, V87(1), P124-6 CAPLUS
  3. ^ The Merck Index. Entry 1009. p. 167.

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