520-53-6

Usage

Uses

Used in Psychedelic Research:
Psilocin is used as a psychomimetic substance in psychedelic research, which aims to study the effects of hallucinogens on human consciousness, perception, and cognition. Its ability to induce altered states of consciousness makes it a valuable tool for understanding the neural mechanisms underlying these experiences.
Used in Controlled Substances:
Psilocin is classified as a controlled substance, specifically a hallucinogen, due to its psychoactive properties. It is regulated in many countries to prevent misuse and ensure that its use is limited to scientific, medical, or research purposes.
Used in Pharmaceutical Development:
As an active neurochemical, psilocin has potential applications in the development of new pharmaceuticals for various conditions. Researchers are exploring its potential therapeutic uses, such as in the treatment of mental health disorders, particularly those involving mood regulation and cognitive function.
Used in Ethnobotanical Studies:
Psilocin is also used in ethnobotanical studies, which focus on the cultural and traditional uses of plants and fungi with psychoactive properties. Understanding the historical and cultural significance of psilocin-containing mushrooms can provide insights into their potential applications and the reasons behind their use in various societies.

InChI:InChI=1/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3

Upstream product

• 28383-23-5 2-(4-(benzyloxy)-1H-indol-3-yl)-N,N-dimethylethan-1-amine 
• 30000-66-9 3-[2-(dimethylamino)-2-oxoacetyl]-1H-indol-4-yl acetate 
• 30000-67-0 2-(4-hydroxy-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide 
• 3965-97-7 O-Methylpsilocine 
• 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 
• 20289-26-3 4-benzyloxy-1H-indole 
• 52061-51-5 4-Benzyloxyindol-3-yl-N,N-dimethylglyoxylamide 
• 52335-79-2 3-(N,N-dimethylaminocarbonylmethyl)-4-methoxyindole 
• 28289-17-0 β-hydroxypsilocin 
• 92292-84-7 2-Acetoxy-N,N-dimethyltryptamine 
• 231620-55-6 methyl N-tert-butoxycarbonyl-4-methoxyindole-3-acetate 
• 142653-08-5 methyl 2-(4-methoxy-1H-indol-3-yl)acetate 

Downstream Products

• 28289-25-0 4-benzoyloxy-3-(2-dimethylamino-ethyl)-indole 
• 92292-84-7 2-Acetoxy-N,N-dimethyltryptamine 
• 94309-54-3 toluene-4-sulfonic acid-[3-(2-dimethylamino-ethyl)-indol-4-yl ester] 
• 1623-08-1 phosphoric acid dibenzyl ester 
• 520-52-5 psilocybin 

Relevant academic research and scientific papers

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.

Observations concerning the synthesis of tryptamine homologues and branched tryptamine derivatives via the borrowing hydrogen process: Synthesis of psilocin, bufotenin, and serotonin

Observations concerning the synthesis of substituted tryptamine derivatives starting from indoles and 1,n-amino alcohols via the borrowing hydrogen process are discussed. This catalytic, single-step, and modular approach to tryptamines and homotryptamines allows the synthesis of branched and nonbranched tryptamines as well as tryptamine-based natural products such as psilocin, bufotenin, and serotonin.

Synthesis and in vitro evaluation of anti-inflammatory activity of ester and amine derivatives of indoline in RAW 264.7 and peritoneal macrophages

A prolonged increase in pro-inflammatory cytokines, TNF-α and IL-6 occurs in inflammatory diseases. Although existing therapies like steroids and TNF-α antagonists are effective they may cause serious adverse effects. We describe the preparation and evaluation for anti-inflammatory activity of 11 novel derivatives of indoline carbamates with a propionic ester, 2-aminoethyl, 3-aminopropyl 2-(dimethylamino)ethyl or 3-(dimethylamino)propyl group in positions 3 or 1. Compounds 25, 26 and 29 were previously shown to inhibit acetylcholinesterase with IC50s ranging from 0.4 to 55 μM and to prevent cytotoxicity induced by reactive oxygen species in a concentration range of 100 pM-1 μM. Compounds 25, 26, 29, 9, 10, 17 and 18, reduced NO, TNF-α and IL-6 at concentrations of 1-10 pM in LPS-activated RAW-264.7 and mouse peritoneal macrophages. The reduction in cytokines by compound 25 was associated with an increase in IκBα degradation and a decrease in the phosphorylation of p38 but not that of ERK. Conclusion: Indoline derivatives substituted at position 3 with chains carrying ester or amino groups may have potential for the treatment of chronic inflammatory and neurodegenerative diseases.

Palladium-catalyzed synthesis of tryptamines and tryptamine homologues: synthesis of psilocin

A new Pd-catalyzed method for the synthesis of tryptamines is developed, and its applications to the synthesis of Corey's aspidophytine tryptamine 15 and psilocin 20 are also described.

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.

A new synthesis of psilocin

A new route to the hallucinogenic alkaloid psilocin, isolated from the mushroom species Psilocybe mexicana, has been established.

H-D exchange of psilocin and its analogs

H-D exchange experiments were performed on psilocin (1) and its analogs in MeOH-d4. The various exchange rates depending on their C3-substituents were observed. The exchange of bufotenine (5) and 5-hydroxyindole (7) is much slower than psilocin (1) and its analogs (2 ~ 4).

A five-step synthesis of psilocin from indole-3-carbaldehyde

A novel preparative method of psilocin was established in only five steps from indole-3-carbaldehyde in 50% overall yield.