Bufotenin

Bufotenin
Clinical data
Other namesBufotenine; 5-Hydroxy-N,N-dimethyltryptamine; 5-HO-DMT; 5-OH-DMT; N,N-Dimethyl-5-hydroxytryptamine; N,N-Dimethylserotonin; Dimethylserotonin; Dimethyl-5-HT; Cebilcin; Mappine
Routes of
administration		Oral, intravenous
ATC code
  • None
Legal status
Legal status
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 Edit this at Wikidata
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)
  • 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 checkY
  • Key:VTTONGPRPXSUTJ-UHFFFAOYSA-N checkY
  (verify)

Bufotenin, also known as dimethylserotonin or as 5-hydroxy-N,N-dimethyltryptamine (5-HO-DMT), is a tryptamine derivative, more specifically, a dimethyltryptamine (DMT) analogue, related to the neurotransmitter serotonin. It is an alkaloid found in some species of mushrooms, plants and toads, especially the skin. It is also found naturally in the human body in small amounts.[1][2][3]

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.[4] 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.

  1. ^ Barker SA, McIlhenny EH, Strassman R (2012). "A critical review of reports of endogenous psychedelic N, N-dimethyltryptamines in humans: 1955-2010". Drug Test Anal. 4 (7–8): 617–635. doi:10.1002/dta.422. PMID 22371425.
  2. ^ Cite error: The named reference NeumannDheinKirchhefer2024 was invoked but never defined (see the help page).
  3. ^ Kärkkäinen J, Forsström T, Tornaeus J, Wähälä K, Kiuru P, Honkanen A, Stenman UH, Turpeinen U, Hesso A (2005). "Potentially hallucinogenic 5-hydroxytryptamine receptor ligands bufotenine and dimethyltryptamine in blood and tissues". Scand J Clin Lab Invest. 65 (3): 189–199. doi:10.1080/00365510510013604. PMID 16095048.
  4. ^ Bufo Alvarius. AmphibiaWeb. Accessed on May 6, 2007.