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

The intentional ingestion of hallucinogenic mushrooms by Mesoamerican natives dates back centuries. Early European explorers documented the Mayan and Aztec symbolism depicting the use of mushroom during spiritual ceremonies. Albert Hofmann first synthesized lysergic acid diethylamide (LSD) from psilocybin extracted from mushrooms. During the 1960s and 1970s, researchers conducted experiments on the utility of psilocybin for psychotherapy before drug laws curbed its use. Psilocybin is described as an entheogen, a substance used to raise spiritual consciousness. Today most countries have outlawed psilocybin possession; however, widespread illicit use continues.

Uses

Different sources of media describe the Uses of 520-52-5 differently. You can refer to the following data:
1. The most common use of this mushroom is to induce recreational hallucinations. Some Native American groups continue to employ psilocybin-containing mushroom species in official ceremonies. The adjunctive use of psilocybin for mainstream psychotherapy has been discontinued. Hallucinogenic mushrooms are generally considered a low-harm drug of abuse.
2. The major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being psilocin. Psychomimetic. Controlled substance (hallucinogen).

Definition

An indole derivative. An alkaloid from certain mushrooms; hallucinogenic drug.

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 
• 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 
• 2380-84-9 7-Indolol 
• 485-80-3 S-adenosyl-L-methionine 
• 15700-23-9 7-Hydroxytryptamine 
• 25198-02-1 7-Hydroxy-L-tryptophan 
• 52061-51-5 4-Benzyloxyindol-3-yl-N,N-dimethylglyoxylamide 
• 28383-23-5 2-(4-(benzyloxy)-1H-indol-3-yl)-N,N-dimethylethan-1-amine 
• 20289-26-3 4-benzyloxy-1H-indole 

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.