Batrachotoxin

Title: Batrachotoxin
CAS Registry Number: 23509-16-2
CAS Name: Batrachotoxinin A 20-(2,4-dimethyl-1H-pyrrole-3-carboxylate)
Additional Names: 3a,9a-epoxy-14b,18b-(epoxyethano-N-methylimino)-5b-pregna-7,16-diene-3b,11a,20a-triol 20a-ester with 2,4-dimethylpyrrole-3-carboxylic acid
Molecular Formula: C31H42N2O6
Molecular Weight: 538.67
Percent Composition: C 69.12%, H 7.86%, N 5.20%, O 17.82%
Literature References: One of a group of toxic steroidal alkaloids consisting of batrachotoxin, pseudobatrachotoxin, homobatrachotoxin, and batrachotoxinin A. Extracted orginally from the skin of South American poison-dart frogs, genus Phyllobates. Its name is derived from the Greek word "batrachos" meaning frog. Isoln: F. Märki, B. Witkop, Experientia 19, 329 (1963); and preliminary characterization: J. W. Daly et al., J. Am. Chem. Soc. 87, 124 (1965). Structure: T. Tokuyama et al., ibid. 91, 3931 (1969). Synthetic studies: J. F. W. Keana, R. R. Schumaker, J. Org. Chem. 41, 3840 (1976); P. Magnus et al., Chem. Commun. 1985, 1185; P. Hudson, Tetrahedron Lett. 34, 7295 (1993). Mode of action: E. X. Albuquerque, Fed. Proc. 31, 1133 (1972). Kinetics and gating action on Na+ channels: J. A. Wasserstrom et al., Biophys. J. 65, 386 (1993). Review: J. Daly, B. Witkop, Clin. Toxicol. 4, 331-342 (1971); of chemistry and pharmacology: E. X. Albuquerque et al., Science 72, 995-1002 (1971); J. W. Daly, Fortschr. Chem. Org. Naturst. 41, 206-227 (1982). Review of sodium channel activation: G. B. Brown, Int. Rev. Neurobiol. 29, 77-116 (1988).
Properties: [a]24584 -5 To -10°; [a]24300 -260° (c = 0.23 in methanol). uv max (0.1N HCl-MeOH): 234, 262 nm (log e 3.99, 3.70). pKa 7.45. LD50 s.c. in mice: 2 mg/kg (Tokuyama).
pKa: pKa 7.45
Optical Rotation: [a]24584 -5 To -10°; [a]24300 -260° (c = 0.23 in methanol)
Absorption maximum: uv max (0.1N HCl-MeOH): 234, 262 nm (log e 3.99, 3.70)
Toxicity data: LD50 s.c. in mice: 2 mg/kg (Tokuyama)
Derivative Type: Batrachotoxinin A
CAS Registry Number: 19457-37-5
Molecular Formula: C24H35NO5
Molecular Weight: 417.54
Percent Composition: C 69.04%, H 8.45%, N 3.35%, O 19.16%
Literature References: Abs config: R. D. Gilardi, Acta Crystallogr. B 26, 440 (1970).
Properties: LD50 s.c. in mice: 1000 mg/kg (Tokuyama).
Toxicity data: LD50 s.c. in mice: 1000 mg/kg (Tokuyama)
Derivative Type: Homobatrachotoxin
CAS Registry Number: 23509-17-3
Additional Names: Isobatrachotoxin
Molecular Formula: C32H44N2O6
Molecular Weight: 552.70
Percent Composition: C 69.54%, H 8.02%, N 5.07%, O 17.37%
Literature References: Also isolated from the feathers and skin of hooded pitohui bird of New Guinea. First demonstration of chemical defense in birds: J. P. Dumbacher et al., Science 258, 799 (1992).
Properties: uv max (0.1N HCl-MeOH): 233, 264 nm (log e 3.95, 3.70). LD50 s.c. in mice: 3 mg/kg (Tokuyama).
Absorption maximum: uv max (0.1N HCl-MeOH): 233, 264 nm (log e 3.95, 3.70)
Toxicity data: LD50 s.c. in mice: 3 mg/kg (Tokuyama)
Use: Biochemical tool for study of Na+ channels.
Batyl Alcohol Bayberry Bark BBOT BCG Bebeerine

Batrachotoxin
Skeletal formula of batrachotoxin
Ball-and-stick model of batrachotoxin
Identifiers
CAS number 23509-16-2 YesY
PubChem 31958
ChemSpider 10310314 YesY
Jmol-3D images Image 1
Properties
Molecular formula C31H42N2O6
Molar mass 538.67 g mol−1
Hazards
Main hazards Highly toxic
LD50 0.002–0.007 mg/kg
(estimated, human, sub-cutaneous)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Batrachotoxins (BTX) are extremely potent cardiotoxic and neurotoxic steroidal alkaloids found in certain species of frogs (poison dart frog), melyrid beetles, and birds (Pitohui, Ifrita kowaldi, Colluricincla megarhyncha).