Mushroom 

The term “mushroom” in a psychoactive context usually refers to fungi containing the naturally occurring compounds psilocybin and psilocin. The mushrooms themselves are biological organisms; the primary psychoactive chemicals are psilocybin and its active metabolite, psilocin.

Psilocybin

• Chemical name (IUPAC):
  [3-(2-dimethylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate
• Molecular formula:
  C₁₂H₁₇N₂O₄P
• Molar mass:
  284.25 g/mol

Chemical class

• Tryptamine derivative
• Indole alkaloid
• Naturally occurring psychedelic compound

Key structural features

• Indole ring system (similar to serotonin)
• Dimethylaminoethyl side chain
• Phosphate ester group attached to the aromatic ring

Functional groups

• Indole heterocycle
• Tertiary amine
• Phosphate ester

Psilocin (active metabolite)

Psilocybin is converted in the body to psilocin, which is primarily responsible for the psychoactive effects.

• Chemical name (IUPAC):
  3-[2-(dimethylamino)ethyl]-1H-indol-4-ol
• Molecular formula:
  C₁₂H₁₆N₂O
• Molar mass:
  204.27 g/mol

Chemical class

• Tryptamine
• Indole alkaloid
• Serotonergic psychedelic

Key structural features

• Indole ring
• Hydroxyl group (-OH) at the 4-position
• Dimethylaminoethyl side chain

Functional groups

• Phenolic hydroxyl group
• Tertiary amine
• Indole heterocycle