Bufotenidine

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]

Bufotenidine

Names
IUPAC name 3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-5-olate
Other names Bufotenidin, N,N,N-trimethylserotonin
Identifiers
CAS Number	487-91-2
3D model (JSmol)	Interactive image
ChemSpider	2340772
PubChem CID	3083591
CompTox Dashboard (EPA)	DTXSID50197595
InChI 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 Key: HIYGARYIJIZXGW-UHFFFAOYSA-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
SMILES C[N+](C)(C)CCC1=CNC2=C1C=C(C=C2)[O-]
Properties
Chemical formula	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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Infobox references

See also

• 2-Methyl-5-HT
• Chlorophenylbiguanide

References

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.