Беоцистин

Description

Baeocystin (N-desmethylpsilocybin) is a natural tryptamine alkaloid found in mushrooms of the genus Psilocybe along with psilocybin and psilocin. It was first isolated in 1967 from Psilocybe baeocystis, hence its name.

Basic Attributes

• CAS No.: 21420-58-6
• Chemical Formula: C11H15N2O4P
• Molecular weight: 270.224
• Exact weight: 270.22
• UNII: 22KW205WF2
• DSSTox ID: DTXSID70175693
• PSA Specifications: 94.6
• XLogP3: -2.1

Physico-chemical characteristics

• Density: 1.447±0.06 g/cm3 (predicted)
• Melting point: 254–258 °C (with decomposition)

Structure and biological activity

Chemically, baeocystin is 4-phosphoryloxy-N-methyltryptamine, an N-monomethylated analogue of psilocybin, characterized by the absence of one methyl group on the amino group of the side chain. Unlike psilocybin, beocystin does not induce the characteristic head shaking response in mice, a standard behavioral marker of serotonin 5-HT2A receptor activation in rodents. In this case, the hydrolysis of baeocystin produces norpsilocin, which is a potent agonist of the 5-HT2A receptor, which indicates the possible role of metabolic activation in the manifestation of the pharmacological activity of the compound.

Scope of application

Beocystine is used as a reference compound and analytical standard in the chemical analysis of psychoactive mushrooms of the genus Psilocybe and related species, as well as in pharmacological studies of the structure-function relationships of tryptamine alkaloids, including for comparison of the activity profile with psilocybin and psilocin in models of serotonin signaling.

Physico-chemical interpretation

A negative XLogP3 value of -2.1 indicates a pronounced hydrophilicity of the molecule due to the phosphate group, which is typical for the entire group of phosphorylated tryptamines (psilocybin, baeocystin, norbaeocystin). The polar surface area of ​​PSA 94.6 Å2 reflects the contribution of phosphate, indole and amine functional groups in the structure of the molecule.

Storage and handling

Beocystin is classified as a controlled substance in most jurisdictions as a structural analogue of psilocybin and is subject to applicable controlled substance legislation and requires special permits. Store in a dry place, protected from light, work using gloves and personal protective equipment when working with powder.

Place among mushroom tryptamines

Along with psilocybin, psilocin and norbaeocystin, baeocystin is part of a group of phosphorylated and non-phosphorylated tryptamines found in the fruiting bodies of mushrooms of the genus Psilocybe in varying proportions depending on the species and growth conditions. The relative content of baeocystin is used as one of the chemotaxonomic characteristics for species identification of fungi of this genus. The density of the substance is estimated at 1.447±0.06 g/cm3.