← DISCOVERY / TRYPTAMINE

Psilocybin

4-PO-DMT

Prodrug that is rapidly dephosphorylated to psilocin in the body. Classic serotonergic psychedelic acting primarily at 5-HT2A 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 10624 · drag to rotate · scroll to zoom
SMILES NOTATION
CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
PubChem CID 10624 →
RECEPTOR PROFILE

The pharmacological targets through which this compound exerts its effects.

5-HT2A agonist5-HT2C5-HT1A
NATURAL SOURCES

Living organisms in which this compound is naturally found.

Conocybe cyanopus (Bluefoot Conocybe)
fungus
Palearctic
Conocybe cyanopus
Bluefoot Conocybe

Small, fragile psilocybin-producing mushroom of well-watered grass and moss. Very easy to overlook and very easy to confuse with several deadly Conocybe and Galerina species — included here for taxonomic completeness rather than as a recommendation.

Explore →
Gymnopilus luteoviridis (Yellow-Green Gymnopilus)
fungus
Nearctic
Gymnopilus luteoviridis
Yellow-Green Gymnopilus

Wood-decaying rust-spored mushroom whose bright golden flesh contains psilocybin alongside an intensely bitter taste — a chemical combination that has prevented it from ever becoming popular for recreational use.

Explore →
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.

Explore →
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.

Explore →
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.

Explore →
Pluteus salicinus (Knackered Cup)
fungus
Palearctic
Pluteus salicinus
Knackered Cup

A pale-grey shield-cap mushroom that grows on rotting willow, beech, and other deciduous wood across Europe and North America. Contains psilocybin and psilocin at modest concentrations — one of the very few psilocybin-producing species outside the Psilocybe and Panaeolus genera.

Explore →
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.

Explore →
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.

Explore →
Psilocybe caerulipes (Blue-Foot)
fungus
Nearctic
Psilocybe caerulipes
Blue-Foot

Small psilocybin-producing mushroom of deciduous hardwood forest east of the Mississippi. The species epithet "caerulipes" — "blue foot" — refers to the strong bluing reaction at the base of the stem when bruised.

Explore →
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.

Explore →
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.

Explore →
Psilocybe mexicana (Teonanácatl)
fungus
Neotropical
Psilocybe mexicana
Teonanácatl

Small psilocybin mushroom historically used in sacred mushroom ceremonies by the Mazatec and other indigenous groups in Mexico.

Explore →
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.

Explore →
Psilocybe pelliculosa (Conifer Psilocybe)
fungus
Nearctic
Psilocybe pelliculosa
Conifer Psilocybe

Slender, conical-capped psilocybin mushroom of Pacific Northwest conifer forest. Lower in psilocybin than P. azurescens or P. cyanescens but far more abundant where it grows — long, narrow troops appearing on conifer debris and old logging tracks in autumn rain.

Explore →
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.

Explore →
Psilocybe stuntzii (Stuntz's Blue Legs)
fungus
Nearctic
Psilocybe stuntzii
Stuntz's Blue Legs

Small to medium psilocybin-producing mushroom of the Pacific Northwest. Famously fond of well-watered urban lawns and wood-chip beds, which has given it the colloquial name "the lawnmower's mushroom". Caution: deadly Galerina marginata grows in the same habitat and is easily confused with it.

Explore →
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.

Explore →
Psilocybe zapotecorum (Hongo de los Zapotecas)
fungus
Neotropical
Psilocybe zapotecorum
Hongo de los Zapotecas

Robust, dark-spored mushroom of Mesoamerican cloud forests, used ceremonially by Zapotec, Chatino, and Mixe peoples and considered one of the sacred 'teonanácatl' species.

Explore →
REFERENCES
Toggle scholarly mode in the footer for inline DOI links
RELATED MOLECULES

Other tryptamines

All compounds →