Bufotenine

Title: Bufotenine
CAS Registry Number: 487-93-4
CAS Name: 3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol
Additional Names: 3-(2-dimethylaminoethyl)-5-indolol; 5-hydroxy-N,N-dimethyltryptamine; N,N-dimethylserotonin; 3-(b-dimethylaminoethyl)-5-hydroxyindole; mappine
Molecular Formula: C12H16N2O
Molecular Weight: 204.27
Percent Composition: C 70.56%, H 7.89%, N 13.71%, O 7.83%
Literature References: Isoln from toads: Wieland et al., Ann. 513, 1 (1934); Wieland, Wieland, ibid. 528, 239 (1937); from toadstools: Wieland, Motzel, ibid. 581, 10 (1953). Isoln from Piptadenia peregrina Benth., Leguminosae: Stromberg, J. Am. Chem. Soc. 76, 1707 (1954). Synthesis: Hoshino, Shimodaira, Ann. 520, 19 (1935); Harley-Mason, Jackson, Chem. Ind. (London) 1952, 954; see also Serotonin; and Speetor, US 2708197 (1955 to Upjohn); Stoll et al., Helv. Chim. Acta 38, 1452 (1955). Activity: Bhattacharya, Sanyal, Indian J. Physiol. Pharmacol. 15, 133 (1971). Crystal and molecular structure: G. Falkenberg, Acta Crystallogr. 28B, 3219 (1972).
Properties: Stout prisms from ethyl acetate, mp 146-147°. bp0.1 320°. uv max: 220, 265 nm (log e 4.0, 3.7). Almost insol in water. Freely sol in alcohol, less sol in ether. Sol in dil acids and alkalies.
Melting point: mp 146-147°
Boiling point: bp0.1 320°
Absorption maximum: uv max: 220, 265 nm (log e 4.0, 3.7)
Derivative Type: Methyliodide
Molecular Formula: C13H19IN2O
Molecular Weight: 346.21
Percent Composition: C 45.10%, H 5.53%, I 36.66%, N 8.09%, O 4.62%
Properties: Stout prisms from methanol, dec 214-215°.
NOTE: This is a controlled substance (hallucinogen): 21 CFR, 1308.11.
Bufotoxin Bufuralol Bulan? Bulbocapnine Bullvalene

Bufotenin
Bufotenin2DACS.svg
Bufotenin 27feb.gif
Systematic (IUPAC) name
3-(2-dimethylaminoethyl)-1H-indol-5-ol
Clinical data
Legal status Prohibited (S9) (AU) Schedule I (US)
Routes Oral, intravenous
Identifiers
CAS number 487-93-4 YesY
ATC code None
PubChem CID 10257
IUPHAR ligand 144
DrugBank DB01445
ChemSpider 9839 YesY
KEGG C08299 YesY
ChEBI CHEBI:3210 YesY
ChEMBL CHEMBL416526 YesY
Synonyms N,N-dimethyl-5-hydroxytryptamine, 5-hydroxy-dimethyltryptamine, bufotenine, cebilcin
Chemical data
Formula C12H16N2O 
Mol. mass 204.268 g/mol
Physical data
Melt. point 146–147 °C (295–297 °F)
Boiling point 320 °C (608 °F)
 YesY (what is this?)  (verify)

Bufotenin (5-HO-DMT, N,N-dimethylserotonin), is a tryptamine related to the neurotransmitter serotonin. It is an alkaloid found in the skin of some species of toads; in mushrooms, higher plants, and mammals.[1]

The name bufotenin originates from the Bufo genus of toads, which includes several species of psychoactive toads, most notably Incilius alvarius, that secrete bufotoxins from their parotoid glands.[2] 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. The psychoactivity of bufotenin has been disputed, though recent studies suggest it is similar in nature to 5-MeO-DMT.