Gephyrotoxin

Title: Gephyrotoxin
CAS Registry Number: 55893-12-4
CAS Name: (1R,3aR,5aR,6R,9aS)-Dodecahydro-6-(2Z)-2-penten-4-ynyl-pyrrolo[1,2-a]-quinoline-1-ethanol
Additional Names: HTX D; histrionicotoxin D
Molecular Formula: C19H29NO
Molecular Weight: 287.44
Percent Composition: C 79.39%, H 10.17%, N 4.87%, O 5.57%
Literature References: Parent member of a class of tricyclic perhydrobenzoindolizine neurotoxin alkaloids isolated from the skin secretions of the Colombian poison-dart frogs Dendrobates histrionicus and Dendrobates occultator, family Dendrobatidae. The name gephyrotoxin was coined from the Greek word "gephyra" meaning "bridge", and refers to the bridge presumably formed by addition of the nitrogen function to one side of a 2,6-disubstituted piperidine precursor to form the bicyclic indolizine. Isolation of naturally occurring l-form: T. Tokuyama et al., Helv. Chim. Acta 57, 2597 (1974). Structure and absolute configuration: J. W. Daly et al., ibid. 60, 1128 (1977). Revised configuration: R. Fujimoto, Y. Kishi, Tetrahedron Lett. 1981, 4197. Total synthesis of (±)-form: R. Fujimoto et al., J. Am. Chem. Soc. 102, 7154 (1980); D. J. Hart, J. Org. Chem. 46, 3576 (1981); D. J. Hart, K. Kanai, J. Am. Chem. Soc. 105, 1255 (1983); L. E. Overman et al., ibid. 5373. Complete proton and 13C NMR assignment: M. W. Edwards, A. Bax, ibid. 108, 918 (1986). Effect on neuromuscular transmission: C. Souccar et al., Mol. Pharmacol. 25, 384, 395 (1984). Receptor binding study: R. S. Aronstam et al., Neurochem. Res. 11, 1227 (1986). Review including discussion of gephyrotoxin congeners: J. W. Daly, Fortschr. Chem. Org. Naturst. 41, 283-300 (see also refs pp 326-340) (1982).
Properties: mp 231-232° (dec). uv max (ethanol): 225 nm (e 8400). [a]D25 -51.5° (c = 1 in ethanol).
Melting point: mp 231-232° (dec)
Optical Rotation: [a]D25 -51.5° (c = 1 in ethanol)
Absorption maximum: uv max (ethanol): 225 nm (e 8400)
Geraniol Geranium Geranylhydroquinone Germane Germanium Dichloride

Gephyrotoxin
Gephyrotoxin.svg
Identifiers
CAS number 55893-12-4
PubChem 6437870
ChemSpider 4942391
Jmol-3D images Image 1
Properties
Molecular formula C19H29NO
Molar mass 287.44 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Gephyrotoxin is a naturally occurring product that stems from the Colombian tropical frog Dendrobates histrionicus. It is a member of the class of compounds known as histrionicotoxins. This alkaloid skin secretion was first isolated from the tropical frog in 1977 by Daly and his fellow workers.[1]