Bufotoxin

Title: Bufotoxin
CAS Registry Number: 464-81-3
CAS Name: [3b(S),5b,16b]-16-(Acetyloxy)-3-[[8-[[4-[(aminoiminomethyl)amino]-1-carboxybutyl]amino]-1,8-dioxooctyl]oxy]-14-hydroxybufa-20,22-dienolide
Additional Names: vulgarobufotoxin; bufotalin 3-suberoylarginine ester
Molecular Formula: C40H60N4O10
Molecular Weight: 756.93
Percent Composition: C 63.47%, H 7.99%, N 7.40%, O 21.14%
Literature References: Principal toxin of the venom of the common European toad, Bufo vulgaris. Isoln and structure: Wieland, Alles, Ber. 55, 1789 (1922); Wieland et al., Ann. 524, 203 (1936); Meyer, Helv. Chim. Acta 32, 1993 (1949); Urscheler et al., ibid. 38, 883 (1955). Alternate structure: Kamano et al., Tetrahedron Lett. 1968, 5673; Linde-Tempel, Helv. Chim. Acta 53, 2188 (1970). Partial synthesis: Pettit, Kamano, Chem. Commun. 1972, 45.
Properties: Monohydrate, bitter needles from alc, dec 205°. uv max: 295 nm (log e 3.74). Freely sol in methanol, pyridine, sparingly sol in abs alc. Practically insol in water, ether, acetone, chloroform, petr ether.
Absorption maximum: uv max: 295 nm (log e 3.74)
Bufuralol Bulan? Bulbocapnine Bullvalene Bumadizon

Bufotoxins are a family of toxic steroid lactones found in the parotoid glands, skin and venom of many toads (genus Bufo); other amphibians; and some plants and mushrooms.[1] The exact composition varies greatly with the specific source of the toxin. It can contain: 5-MeO-DMT, bufagins, bufalin, bufotalin, bufotenin, bufothionine, epinephrine, norepinephrine, and serotonin. The term bufotoxin can also be used specifically to describe the conjugate of a bufagin with suberylargine.[2]

The toxic substances found in toads can be divided by chemical structure in two groups:

  • bufadienolides which are cardiac glycosides (e.g. bufotalin, bufogenin)
  • tryptamine related substances (e.g. bufotenin)


Toads known to secrete bufotoxin are:[citation needed]

  • Bufo alvarius
  • Bufo americanus
  • Bufo arenarum
  • Bufo asper
  • Bufo blombergi
  • Bufo boreas
  • Bufo bufo
  • Bufo bufo gargarizans
  • Bufo formosus
  • Bufo fowleri
  • Bufo marinus
  • Bufo melanostictus
  • Bufo peltocephalus
  • Bufo quercicus
  • Bufo regularis
  • Bufo valliceps
  • Bufo viridis
  • Bufo vulgaris