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.

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