Psilocybin: Difference between revisions
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Psilocybin. | '''Psilocybin''' (4-phosphoryloxy-N,N-dimethyltryptamine): | ||
Also known as: C<sub>12</sub>H<sub>17</sub>N<sub>2</sub>O<sub>4</sub>P, 4-PO-DMT, psilocybine, (3-[2-(dimethylamino)-ethyl]-1H-indol-4-ol dihydrogen phosphate) | |||
Psilocybin is a naturally occurring tryptamine alkaloid and psychedelic secondary metabolite that is a prodrug compound produced by more than 200 species of fungi. It is a substituted tryptamine that features an indole ring linked to an aminoethyl substituent. It is structurally similar to serotonin. Psilocybin is a member of the general class of tryptophan-based compounds that originally functioned as antioxidants in earlier life forms before assuming more complex functions in multicellular organisms, including humans. | |||
As a prodrug, psilocybin itself is biologically inactive. It is quickly converted by the body to [[psilocin]] by a dephosphorylation reaction mediated by alkaline phosphatase enzymes. | |||
It was first isolated from fruiting bodies of Psilocybe mexicana cultivated by Albert Hofmann in 1957. | |||
Molecular weight: 248.248 gᐧmol-1 | |||
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Melting point 224 °C (220-228 oC)[6] | |||
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Ammonia-like taste[6] | |||
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Relatively stable, white crystalline powder (in pure form)[3] | |||
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Can be recrystallized from boiling water | |||
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Unstable in light (particularly while in solution)[3][6] + sensitive to temperature[59] | |||
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pKa values: | |||
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* 1.3 and 6.5 for two consecutive phosphate hydroxyl groups | |||
* 10.4 for the dimethylamine nitrogen | |||
Typically exists as a zwitterionic structure | |||
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Soluble in water, methanol and ethanol | |||
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Insoluble in organic solvents | |||
== References == | |||
[[Category:Psychedelics]] | |||
Latest revision as of 23:30, 29 November 2025
Psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine): Also known as: C12H17N2O4P, 4-PO-DMT, psilocybine, (3-[2-(dimethylamino)-ethyl]-1H-indol-4-ol dihydrogen phosphate)
Psilocybin is a naturally occurring tryptamine alkaloid and psychedelic secondary metabolite that is a prodrug compound produced by more than 200 species of fungi. It is a substituted tryptamine that features an indole ring linked to an aminoethyl substituent. It is structurally similar to serotonin. Psilocybin is a member of the general class of tryptophan-based compounds that originally functioned as antioxidants in earlier life forms before assuming more complex functions in multicellular organisms, including humans.
As a prodrug, psilocybin itself is biologically inactive. It is quickly converted by the body to psilocin by a dephosphorylation reaction mediated by alkaline phosphatase enzymes.
It was first isolated from fruiting bodies of Psilocybe mexicana cultivated by Albert Hofmann in 1957.
Molecular weight: 248.248 gᐧmol-1
Melting point 224 °C (220-228 oC)[6]
Ammonia-like taste[6]
Relatively stable, white crystalline powder (in pure form)[3]
Can be recrystallized from boiling water
Unstable in light (particularly while in solution)[3][6] + sensitive to temperature[59]
pKa values:
- 1.3 and 6.5 for two consecutive phosphate hydroxyl groups
- 10.4 for the dimethylamine nitrogen
Typically exists as a zwitterionic structure
Soluble in water, methanol and ethanol
Insoluble in organic solvents