520-52-5

Basic information

• Product Name: psilocybine
• Synonyms: INDOL-4-OL,3-(2-DIMETHYLAMINO)ETHYL)-DIHYDROGENPHOSPHATE;3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol 4-Dihydrogen Phosphate Ester;4-Phosphoryl-N,N-dimethyltryptamine;Cy 39;Indocybin;O-Phosphoryl-4-hydroxy-N,N-dimethyltryptamine;Psilocine Phosphate;3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl phosphate
• CAS NO: 520-52-5
• Molecular Formula: C₁₂H₁₇N₂O₄P
• Molecular Weight: 284.25
• EINECS: 208-294-4
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Phosphorylating and Phosphitylating Agents;Indole Derivatives
• Mol File: 520-52-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 220-2280C
• Boiling Point: 523.4°Cat760mmHg
• Flash Point: 2℃
• Appearance: /solid
• Density: 1.409g/cm³
• Vapor Pressure: 8.75E-12mmHg at 25°C
• Refractive Index: 1.644
• Storage Temp.: −20°C
• PKA: 1.25±0.30(Predicted)
• CAS DataBase Reference: psilocybine(CAS DataBase Reference)
• NIST Chemistry Reference: psilocybine(520-52-5)
• EPA Substance Registry System: psilocybine(520-52-5)

Safety Data

• RIDADR: 1544
• WGK Germany: 1
• RTECS: NM3150000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 520-52-5(Hazardous Substances Data)

Usage

Description

Psilocybin, an indole derivative and alkaloid found in certain mushrooms, is a naturally occurring hallucinogenic drug. It has been used for centuries by Mesoamerican natives, particularly in spiritual ceremonies, and is described as an entheogen, a substance used to raise spiritual consciousness. Although psilocybin possession is now outlawed in most countries, its illicit use remains widespread.

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

• 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 
• 28289-17-0 β-hydroxypsilocin 
• 30000-66-9 3-[2-(dimethylamino)-2-oxoacetyl]-1H-indol-4-yl acetate 
• 952006-34-7 3-(2-chloro-2-oxoacetyl)-1H-indol-4-yl acetate 
• 5585-96-6 acetic acid 1H-indol-4-yl ester 
• 2380-94-1 1H-indol-4-ol 
• 20289-26-3 4-benzyloxy-1H-indole 
• 520-53-6 psilocin 

Relevant articles and documents

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.

A biosynthetic sequence from tryptophan to psilocybin.

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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.