← DISCOVERY / TRYPTAMINE

Baeocystin

4-PO-NMT

Naturally occurring psilocybin analog found in many Psilocybe species. Thought to be a prodrug similar to psilocybin with potentially milder or distinct subjective character.

psychedelic
THREE-DIMENSIONAL STRUCTURE

The molecule, in space.

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

3D structure · PubChem CID 161264 · drag to rotate · scroll to zoom
SMILES NOTATION
CN(C)CC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
PubChem CID 161264 →
RECEPTOR PROFILE

The pharmacological targets through which this compound exerts its effects.

5-HT2A agonist (presumed)
NATURAL SOURCES

Living organisms in which this compound is naturally found.

Inocybe aeruginascens (Aeruginous Fibrecap)
fungus
Palearctic
Inocybe aeruginascens
Aeruginous Fibrecap

Small European fibrecap that, uniquely within an otherwise toxic genus, produces psilocybin, baeocystin, and the quaternary tryptamine aeruginascin — the latter discovered through accidental poisonings.

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Panaeolus cinctulus (Banded Mottlegill)
fungus
Palearctic
Panaeolus cinctulus
Banded Mottlegill

Widely distributed, moderately potent psilocybin-containing mushroom — one of the most common temperate dung and compost species, and often the first encountered by accidental foragers.

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Panaeolus cyanescens (Copelandia cyanescens)
fungus
Neotropical
Panaeolus cyanescens
Copelandia cyanescens

Pantropical dung-loving mushroom widely regarded as one of the most potent natural sources of psilocybin and psilocin — often several times stronger by weight than Psilocybe cubensis.

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Psilocybe azurescens (Flying Saucer Mushroom)
fungus
Nearctic
Psilocybe azurescens
Flying Saucer Mushroom

One of the most potent psilocybin-containing mushrooms in the world. Produces exceptionally high levels of psilocybin and psilocin.

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Psilocybe baeocystis (Bottle Cap)
fungus
Nearctic
Psilocybe baeocystis
Bottle Cap

Wood-loving Pacific Northwest mushroom and the type species for the alkaloid baeocystin. Often dark, sticky, and prone to staining a deep indigo blue.

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Psilocybe cubensis (Golden Teacher)
fungus
Neotropical
Psilocybe cubensis
Golden Teacher

One of the most widely cultivated and studied psilocybin-producing mushrooms. Cosmopolitan species with a distinctive golden cap and strong blue bruising reaction.

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Psilocybe cyanescens (Wavy Cap)
fungus
Nearctic
Psilocybe cyanescens
Wavy Cap

Highly potent wood-loving psilocybin mushroom famous for its wavy cap margin and intense blue bruising. One of the strongest naturally occurring species in temperate climates.

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Psilocybe natalensis (Natal Super Strength)
fungus
Afrotropical
Psilocybe natalensis
Natal Super Strength

Southern African dung-loving psilocybin mushroom morphologically similar to P. cubensis but adapted to subtropical grassland conditions.

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Psilocybe semilanceata (Liberty Cap)
fungus
Palearctic
Psilocybe semilanceata
Liberty Cap

Small, potent, conical-capped mushroom that is among the most widespread psilocybin species in temperate regions.

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Psilocybe tampanensis (Philosopher's Stone)
fungus
Nearctic
Psilocybe tampanensis
Philosopher's Stone

Rare wild mushroom famous for producing dense underground sclerotia — the so-called 'magic truffles' that have become the legal substrate for psilocybin retreats and microdosing in the Netherlands.

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REFERENCES
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  • Stamets 1996
  • Guzmán 2000
RELATED MOLECULES

Other tryptamines

All compounds →