Bufotenidine

Bufotenidine, also known as 5-hydroxy-N,N,N-trimethyltryptammonium (5-HTQ), is an indole 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 serotonin 5-HT₃ receptor agonist, and has been used in scientific research to study the function of the serotonin 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 and hence is peripherally selective.^[3]

Bufotenidine

Names
Preferred IUPAC name 3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-5-olate
Other names Bufotenidin, N,N,N-Trimethylserotonin
Identifiers
CAS Number	487-91-2 Y
3D model (JSmol)	Interactive image
ChemSpider	2340772 N
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 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
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). N verify (what is YN ?) Infobox references

See also

• 4-HO-TMT
• Aeruginascin
• 2-Methyl-5-HT
• Chlorophenylbiguanide