← DISCOVERY / TRYPTAMINE

Bufotenine

5-HO-DMT

Naturally occurring tryptamine found in certain toads, plants, and fungi. Has complex pharmacology with activity at serotonin receptors.

psychedelic
THREE-DIMENSIONAL STRUCTURE

The molecule, in space.

Atoms positioned in their lowest-energy 3D geometry, sourced from PubChem. Drag to rotate · pinch or scroll to zoom · switch between stick, sphere, and line representations to feel the shape from different angles.

3D structure · PubChem CID 10257 · drag to rotate · scroll to zoom
SMILES NOTATION
CN(C)CCC1=CNC2=C1C=C(C=C2)O
PubChem CID 10257 →
RECEPTOR PROFILE

The pharmacological targets through which this compound exerts its effects.

5-HT2A5-HT1A
NATURAL SOURCES

Living organisms in which this compound is naturally found.

Anadenanthera colubrina (Cebil)
plant
Andean
Anadenanthera colubrina
Cebil

South American tree whose seeds have been prepared into psychoactive snuff (vilca) and brews for at least three thousand years. Closely related to yopo but distributed further south, across the central Andes and the Gran Chaco.

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Anadenanthera peregrina (Yopo)
plant
Neotropical
Anadenanthera peregrina
Yopo

Tree native to the Caribbean and northern South America whose seeds contain a powerful mix of bufotenine, DMT, and 5-MeO-DMT. The seeds are roasted and ground into the snuff known as yopo, used in shamanic ceremonies of the Orinoco basin.

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Bufo bufo (Common Toad)
animal
Palearctic
Bufo bufo
Common Toad

Widespread Eurasian toad whose parotoid secretion contains bufotenine, bufotalin, and other bufadienolides at lower concentration than Rhinella marina. Of more historical and cultural than pharmacological interest — repeatedly named in early-modern European witch-trial confessions and herbals as an ingredient in flying ointments and brews.

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Incilius alvarius (Sonoran Desert Toad)
animal
Sonoran Desert
Incilius alvarius
Sonoran Desert Toad

Large toad native to the Sonoran Desert whose parotoid glands contain significant amounts of 5-MeO-DMT and bufotenine.

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Phalaris arundinacea (Reed Canary Grass)
plant
Palearctic
Phalaris arundinacea
Reed Canary Grass

Widespread temperate grass with extremely variable alkaloid chemistry — depending on the strain and growing conditions, it can produce N,N-DMT, 5-MeO-DMT, bufotenine, and the toxic gramine in differing ratios.

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Phyllodium pulchellum (Mountain Locust)
plant
Indomalayan
Phyllodium pulchellum
Mountain Locust

Small flowering shrub of the legume family, native to a broad sweep of tropical and subtropical Asia. Phytochemical surveys have repeatedly shown its leaves and roots to contain a striking combination of psychoactive tryptamines — N,N-DMT, 5-MeO-DMT, and bufotenine — alongside β-carboline alkaloids of the harmala family, making it one of the very few single plants to carry both halves of the ayahuasca formula in the same organism.

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Rhinella marina (Cane Toad)
animal
Neotropical
Rhinella marina
Cane Toad

Very large bufonid toad native to Central and South America, infamous worldwide as one of the most damaging invasive species after deliberate introduction to Australia, the Caribbean and many Pacific islands. The parotoid glands secrete a complex toxin cocktail including bufotenine, bufotalin, and cardiac glycosides.

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Virola theiodora (Epená)
plant
Amazonian
Virola theiodora
Epená

Tall Amazonian rainforest tree whose red resin is processed into a powerful DMT-rich snuff used by Yanomami, Tukano, and several other northwest-Amazonian peoples.

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REFERENCES
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  • Davis 1987
RELATED MOLECULES

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