Bufotenidine

Bufotenidine
Names
Preferred IUPAC name
3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-5-olate
Other names
Bufotenidin, N,N,N-Trimethylserotonin
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C13H18N2O/c1-15(2,3)7-6-10-9-14-13-5-4-11(16)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3 ☒N
    Key: HIYGARYIJIZXGW-UHFFFAOYSA-N ☒N
  • InChI=1/C13H18N2O/c1-15(2,3)7-6-10-9-14-13-5-4-11(16)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
    Key: HIYGARYIJIZXGW-UHFFFAOYAI
  • C[N+](C)(C)CCC1=CNC2=C1C=C(C=C2)[O-]
Properties
C13H18N2O
Molar mass 218.300 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bufotenidine, also known as 5-hydroxy-N,N,N-trimethyltryptammonium (5-HTQ), is a toxin related to bufotenin, serotonin, and other tryptamines which is found in the venom of a variety of toads.[1][2] It acts as a selective 5-HT3 receptor agonist, and has been used in scientific research to study the function of the 5-HT3 receptor, though this use has been limited by the fact that, as a quaternary amine, it is unable to readily cross the blood-brain-barrier.[3]

  1. ^ Wieland, Heinrich; Konz, Wilhelm; Mittasch, Heinz (1934). "Toad poisons. VII. Constitution of bufotenin and bufotenidine". Justus Liebigs Annalen der Chemie. 513: 1–25. doi:10.1002/jlac.19345130102.
  2. ^ Raymond-Hamet (1943). "Bufotenidine, an extremely active principle of the venom of the common toad (Bufo bufo)". Comptes rendus des séances de la Société de biologie et de ses filiales. 137: 74–75.
  3. ^ Bryan L. Roth (17 August 2008). The Serotonin Receptors: From Molecular Pharmacology to Human Therapeutics. Springer Science & Business Media. pp. 108–. ISBN 978-1-59745-080-5.