Bufotenine N-Oxide

Bufotenine N-Oxide

Bufotenine N-oxide is a tryptamine found naturally in several plants. It's the N-Oxide form of the hallucinogen bufotenine. It can be converted to bufotenine using zinc dust in aqueous acetic acid.[1] Bufotenine can be oxidized to bufotenine N-oxide by the action of peroxide in ethanol.[1] Bufotenine can also form bufotenine N-oxide by prolonged exposure to air.

Natural Sources

Anadenanthera colubrina seeds[1]
Anadenanthera peregrina seeds[1]
Desmodium caudatum roots and stems[1]
Desmodium pulchellum roots, stems, and leaves[1]


The psyhoactivity of bufotenine N-oxide in humans has not been studied.

Chemical Properties

Appearance: Rods[1]

  • 3-[2-(Dimethylnitroryl)ethyl]-1H-indol-5-ol
  • Bufotenine-N-oxide
  • Bufotenin oxide
  • 2-(5-hydroxy-1H-indol-3-yl)-N,N-dimethylethanamine oxide
  • 1H-Indol-5-ol, 3-(2-(dimethylamino)ethyl)-, N-oxide

IUPAC Name: 2-(5-hydroxy-1H-indol-3-yl)-N,N-dimethylethanamine oxide
CAS Number: 1019-44-9
Molecular Formula: C12H16N2O2
Molecular Weight: 220.26764 g/mol
Melting Point: 217 C; 214-215 C; 211-214 C (no water of hydration, after being washed with ether and dried at room temperature)[1]
Boiling Point: Unknown. Predicted by EPISuite™ to be 563.27 C. Note that EPISuite™ also predicts it's melting point to be 242.15 C, which is a bit off.
InChI: InChI=1S/C12H16N2O2/c1-14(2,16)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
Canonical SMILES: C[N+](C)(CCC1=CNC2=C1C=C(C=C2)O)[O-]
ChemSpider ID: 2340840
PubChem CID: 3083669
Solubility: Unknown. Predicted by EPISuite™ to be soluble in water at 801.29 mg/L.

See also

The Yopo Transformation Theory

1. Some Simple Tryptamines
Friends, Keeper of the Trout &: Mydriatic Productions, 2007; ISBN 0977087654, 9780977087655
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