952006-34-7

Upstream product

• 79-37-8 oxalyl dichloride 
• 5585-96-6 acetic acid 1H-indol-4-yl ester 
• 2380-94-1 1H-indol-4-ol 

Downstream Products

• 520-52-5 psilocybin 
• 791537-89-8 3-(2-(dibenzylamino)ethyl)-1H-indol-4-ol 
• 21420-58-6 [3-(2-methylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate 
• 77872-23-2 3-(2-(dibenzylamino)-2-oxoacetyl)-1H-indol-4-yl acetate 
• 92292-84-7 2-Acetoxy-N,N-dimethyltryptamine 
• 1154742-29-6 C₂₃H₂₁N₃O₅ 
• 520-53-6 psilocin 

Relevant academic research and scientific papers

AZETIDINYL TRYPTAMINES AND METHODS OF TREATING PSYCHIATRIC DISORDERS

The present disclosure includes azetidinyl tryptamines and methods of treating psychiatric disorders with such compounds. Also provided are pharmaceutical compositions that include azetidinyl tryptamines.

Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin

A general synthetic method was developed to access known tryptamine natural products present in psilocybin-producing mushrooms. In vitro and in vivo experiments were then conducted to inform speculations on the psychoactive properties, or lack thereof, of the natural products. In animal models, psychedelic activity by baeocystin alone was not evident using the mouse head twitch response assay, despite its putative dephosphorylated metabolite, norpsilocin, possessing potent agonist activity at the 5-HT2A receptor.

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.

Inhibitors of HIV-1 attachment. Part 2: An initial survey of indole substitution patterns

The effects of introducing simple halogen, alkyl, and alkoxy substituents to the 4, 5, 6 and 7 positions of 1-(4-benzoylpiperazin-1-yl)-2-(1H-indol-3-yl)ethane-1,2-dione, an inhibitor of the interaction between HIV gp120 and host cell CD4 receptors, on activity in an HIV entry assay was examined. Small substituents at C-4 generally resulted in increased potency whilst substitution at C-7 was readily tolerated and uniformly produced more potent HIV entry inhibitors. Substituents deployed at C-6 and, particularly, C-5 generally produced a modest to marked weakening of potency compared to the prototype. Small alkyl substituents at N-1 exerted minimal effect on activity whilst increasing the size of the alkyl moiety led to progressively reduced inhibitory properties. These studies establish a basic understanding of the indole element of the HIV attachment inhibitor pharmacophore.

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.