Bufotenin

Bufotenin (5-HO-DMT, bufotenine) is a tryptamine derivative, more specifically, a DMT analog, related to the neurotransmitter serotonin. It is an alkaloid found in some species of mushrooms, plants and toads, especially the skin.

Bufotenin
Clinical data
Other namesN,N-Dimethyl-5-hydroxytryptamine; 5-Hydroxy-dimethyltryptamine; Bufotenine; Cebilcin
Routes of
administration		Oral, intravenous
ATC code
  • none
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA: Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Schedule I
  • Illegal in Sweden
Identifiers
  • 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.971
Chemical and physical data
FormulaC12H16N2O
Molar mass204.273 g·mol−1
3D model (JSmol)
Melting point146 to 147 °C (295 to 297 °F)
Boiling point320 °C (608 °F)
SMILES
  • CN(C)CCc1c[nH]c2ccc(O)cc12
  • InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3 Y
  • Key:VTTONGPRPXSUTJ-UHFFFAOYSA-N Y
  (verify)

The name bufotenin originates from the toad genus Bufo, which includes several species of psychoactive toads, most notably Incilius alvarius, that secrete bufotoxins from their parotoid glands. Bufotenin is similar in chemical structure to the psychedelics psilocin (4-HO-DMT), 5-MeO-DMT and DMT, chemicals which also occur in some of the same fungus, plant and animal species as bufotenin.

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