520-52-5

Usage

Uses

Used in Recreational Hallucinations:
Psilocybin is used as a recreational hallucinogen for inducing altered states of consciousness and sensory experiences. Its popularity stems from its ability to provoke vivid hallucinations, changes in perception, and a sense of euphoria.
Used in Spiritual Ceremonies:
In some Native American groups, psilocybin-containing mushroom species are employed in official ceremonies, where they are used as entheogens to facilitate spiritual experiences and connect with the divine.
Used in Psychotherapy (Historic):
During the 1960s and 1970s, psilocybin was investigated for its potential utility in psychotherapy. It was used as an adjunctive treatment to help patients explore their inner psyche and address various psychological issues. However, due to changes in drug laws, this use has been discontinued in mainstream medicine.
Used as a Controlled Substance:
Psilocybin is classified as a controlled substance (hallucinogen) due to its psychoactive effects and potential for abuse. Its regulation aims to prevent misuse and ensure that its use is limited to appropriate contexts, such as research or specific cultural practices.

Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal route. Human systemic effects by ingestion and intraperitoneal routes: euphoria, hallucinations, toxic psychosis, muscle weakness, nausea or vomiting, visual field changes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and POx.

InChI:InChI=1/C12H17N2O4P/c1-14(2)7-6-9-8-13-10-4-3-5-11(12(9)10)18-19(15,16)17/h3-5,8,13H,6-7H2,1-2H3,(H2,15,16,17)

Upstream product

• 520-53-6 psilocin 
• 20289-26-3 4-benzyloxy-1H-indole 
• 28383-23-5 2-(4-(benzyloxy)-1H-indol-3-yl)-N,N-dimethylethan-1-amine 
• 52061-51-5 4-Benzyloxyindol-3-yl-N,N-dimethylglyoxylamide 
• 25198-02-1 7-Hydroxy-L-tryptophan 
• 15700-23-9 7-Hydroxytryptamine 
• 485-80-3 S-adenosyl-L-methionine 
• 2380-84-9 7-Indolol 
• 2380-94-1 1H-indol-4-ol 
• 5585-96-6 acetic acid 1H-indol-4-yl ester 
• 952006-34-7 3-(2-chloro-2-oxoacetyl)-1H-indol-4-yl acetate 
• 30000-66-9 3-[2-(dimethylamino)-2-oxoacetyl]-1H-indol-4-yl acetate 
• 28289-17-0 β-hydroxypsilocin 

Relevant academic research and scientific papers

Scalable Hybrid Synthetic/Biocatalytic Route to Psilocybin

Psilocybin, the principal indole alkaloid of Psilocybe mushrooms, is currently undergoing clinical trials as a medication against treatment-resistant depression and major depressive disorder. The psilocybin supply for pharmaceutical purposes is met by synthetic chemistry. We replaced the problematic phosphorylation step during synthesis with the mushroom kinase PsiK. This enzyme was biochemically characterized and used to produce one gram of psilocybin from psilocin within 20 minutes. We also describe a pilot-scale protocol for recombinant PsiK that yielded 150 mg enzyme in active and soluble form. Our work consolidates the simplicity of tryptamine chemistry with the specificity and selectivity of enzymatic catalysis and helps provide access to an important drug at potentially reasonable cost.

An Improved, Practical, and Scalable Five-Step Synthesis of Psilocybin

Described herein is an improved synthesis of 3-[2-(dimethylamino)ethyl]-1 H -indol-4-yl dihydrogen phosphate (psilocybin). The protocol outlines: synthesis of multigram quantities of psilocybin, identification of critical in-process parameters, and isolation of psilocybin without the use of chromatography, TLC, or aqueous workup. The synthesis furnishes psilocybin in five steps in 23percent overall yield from an inexpensive acetoxyindole starting material. With specific focus on process control and impurity fate and removal, the improved procedure is amenable to providing high-quality psilocybin.

PREPARATION OF PSILOCYBIN, DIFFERENT POLYMORPHIC FORMS, INTERMEDIATES, FORMULATIONS AND THEIR USE

This invention relates to the large-scale production of psilocybin for use in medicine. More particularly, it relates to a method of obtaining high purity crystalline psilocybin, particularly, in the form of Polymorph A. It further relates to a method for the manufacture of psilocybin and intermediates in the production thereof and formulations containing psilocybin.

Biocatalytic Production of Psilocybin and Derivatives in Tryptophan Synthase-Enhanced Reactions

Psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine) is the main alkaloid of the fungal genus Psilocybe, the so-called “magic mushrooms.” The pharmaceutical interest in this psychotropic natural product as a future medication to treat depression and anxiety is strongly re-emerging. Here, we present an enhanced enzymatic route of psilocybin production by adding TrpB, the tryptophan synthase of the mushroom Psilocybe cubensis, to the reaction. We capitalized on its substrate flexibility and show psilocybin formation from 4-hydroxyindole and l-serine, which are less cost-intensive substrates, compared to the previous method. Furthermore, we show enzymatic production of 7-phosphoryloxytryptamine (isonorbaeocystin), a non-natural congener of the Psilocybe alkaloid norbaeocystin (4-phosphoryloxytryptamine), and of serotonin (5-hydroxytryptamine) by means of the same in vitro approach.

Concise large-scale synthesis of psilocin and psilocybin, principal hallucinogenic constituents of "magic mushroom"

The concise large-scale syntheses of psilocin (1) and psilocybin (2), the principal hallucinogenic constituents of "magic mushroom", were achieved without chromatographic purification. The key step in the synthesis of 2 was the isolation of the dibenzyl-protected intermediate (7) as a zwitterionic derivative (8), which was completely identified by means of 2D NMR analyses.

Improvements to the synthesis of psilocybin and a facile method for preparing the O-acetyl prodrug of psilocin

An improved procedure to accomplish the O-phosphorylation of 4-hydroxy- N,N-dimethyltryptamine (psilocin 5) is reported that utilizes reaction between the O-lithium salt of 5 and tetra-O-benzylpyrophosphate. The O- benzyl groups were removed by catalytic hydrogenation over palladium on carbon to afford N,N-dimethyl-4-phosphoryloxytryptamine (psilocybin, 1). In view of difficulties encountered in the preparation of 1, it is suggested that 4-acetoxy-N,N-dimethyltryptamine (2) may be a useful alternative for pharmacological studies. The latter was obtained following catalytic O- debenzylation of 4-benzyloxy-N,N-dimethyltryptamine in the presence of acetic anhydride and sodium acetate.