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Aeruginascin

N,N,N-trimethyl-4-phosphoryloxytryptamine

Quaternary tryptamine analog of psilocybin found in Inocybe aeruginascens, Panaeolus cyanescens, and several Psilocybe species. The fixed positive charge limits its passage into the brain, and current evidence suggests it may modulate the subjective character of the experience rather than acting as a primary psychedelic.

psychedelic
Chemical structure of Aeruginascin
Structure · Wikimedia contributor See Wikimedia
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 14739663 · drag to rotate · scroll to zoom
SMILES NOTATION
C[N+](C)(C)CCc1c[nH]c2cccc(OP(=O)(O)O)c12
PubChem CID 14739663 →
RECEPTOR PROFILE

The pharmacological targets through which this compound exerts its effects.

5-HT2A (limited CNS penetration)
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 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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REFERENCES
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RELATED MOLECULES

Other tryptamines

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Chemical structure of 5-Methoxy-N,N-dimethyltryptamine
Tryptamine
15–45 minutes
5-Methoxy-N,N-dimethyltryptamine
5-MeO-DMT
psychedelic

Potent 5-HT1A and 5-HT2A agonist. Produces an extremely intense, short-duration experience often described as complete ego dissolution or 'whiteout'.

Incilius alvariusAnadenanthera peregrinaVirola theiodora +1 more
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Chemical structure of Baeocystin
Tryptamine
3–5 hours
Baeocystin
4-PO-NMT
psychedelic

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

Psilocybe cyanescensPsilocybe azurescensPsilocybe semilanceata +7 more
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Chemical structure of Bufotenine
Tryptamine
Varies
Bufotenine
5-HO-DMT
psychedelic

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

Incilius alvariusAnadenanthera peregrinaAnadenanthera colubrina +2 more
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Chemical structure of N,N-Dimethyltryptamine
Tryptamine
5–20 minutes (vaporized) / 4–8 hours (ayahuasca)
N,N-Dimethyltryptamine
DMT
psychedelic

Extremely potent serotonergic psychedelic. Rapidly metabolized by MAO when taken orally, hence the need for MAO inhibitors in ayahuasca.

Psychotria viridisDiplopterys cabreranaAcacia confusa +8 more
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