Back سمين ضفدعي Arabic Batracotoxina Catalan Batrachotoxin Czech Batrachotoxin German Batracotoxina Spanish باتراکوتوکسین Persian Batrakotoksiinit Finnish Batrachotoxine French Batracotossina Italian バトラコトキシン Japanese

Batrachotoxin

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
3D model (JSmol)
ChemSpider
UNII
  • 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
  • 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
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):
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 ?)

Batrachotoxin (BTX) is an extremely potent cardiotoxic 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 Crystallographica Section B. 25 (3): 428–434. Bibcode:1969AcCrB..25..428K. doi:10.1107/S056774086900238X. PMID 5820223. S2CID 28609553.
  2. ^ Daly, J. W.; Witkop, B.; Bommer, P.; Biemann, K. (January 1965). "Batrachotoxin. The Active Principle of the Colombian Arrow Poison Frog, Phyllobates bicolor". Journal of the American Chemical Society. 87 (1): 124–126. doi:10.1021/ja01079a026. PMID 5826972.
  3. ^ The Merck Index. Entry 1009. p. 167.

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