Bufotenin

Bufotenin

Clinical data
Other names	N,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
IUPAC name 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol
CAS Number	487-93-4 Y
PubChem CID	10257
IUPHAR/BPS	144
DrugBank	DB01445 Y
ChemSpider	9839 Y
UNII	0A31347TZK
KEGG	C08299 Y
ChEBI	CHEBI:3210 Y
ChEMBL	ChEMBL416526 Y
CompTox Dashboard (EPA)	DTXSID0048894
ECHA InfoCard	100.006.971
Chemical and physical data
Formula	C12H16N2O
Molar mass	204.273 g·mol−1
3D model (JSmol)	Interactive image
Melting point	146 to 147 °C (295 to 297 °F)
Boiling point	320 °C (608 °F)
SMILES CN(C)CCc1c[nH]c2ccc(O)cc12
InChI 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
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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.

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.^[1] 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.