Toxiferine

Summary

Toxiferine (C-toxiferine I) is a curare toxin. It is a bisindole alkaloid derived from Strychnos toxifera and a nicotinic acetylcholine receptor antagonist. This alkaloid is the main toxic component of Calabash curare, and one of the most toxic plant alkaloids known. The lethal dose (LD50) for mice has been determined as 10 - 60 µg/kg by intravenous administration.[1] It is a muscle relaxant that causes paralysis of skeletal muscle, which takes approximately 2 hours to recovery for a moderate dose, and 8 hours of total paralysis with a 20-fold paralytic dose. The paralysis can be antagonized by neostigmine[2]

Toxiferine
Identifiers
CAS Number
  • 302-30-7
PubChem CID
  • 5281411
ChemSpider
  • 4444760
UNII
  • 9M7D9K3OJI
ChEMBL
  • ChEMBL231047
CompTox Dashboard (EPA)
  • DTXSID30897243 Edit this at Wikidata
Chemical and physical data
FormulaC40H46N4O2
Molar mass614.834 g·mol−1
3D model (JSmol)
  • Interactive image
  • [H][C@@]12[C@@]3(CC[N+]2(C)C/C4=C/CO)[C@@]5([H])N(C6=C3C=CC=C6)/C=C7[C@]([C@@]8(CC[N+]9(C)C/%10)[C@]9([H])C[C@]\7([H])C%10=C/CO)([H])N(C%11=C8C=CC=C%11)/C=C5/[C@]4([H])C1

References edit

  1. ^ Entry on C-Toxiferine I. at: Römpp Online. Georg Thieme Verlag, retrieved 8 June 2020.
  2. ^ Saxton JE, Gorman AA, Hesse M, Schmid H, Waser PG, Hopff WH (1971). "Bisindole alkaloids". In Saxton JE (ed.). The Alkaloids: v. 1: A Review of Chemical Literature. Specialist Periodical Reports. Cambridge, Eng: Royal Society of Chemistry. p. 330. ISBN 0-85186-257-8.