28383-23-5

Basic information

• Product Name: O-Benzyl Psilocin
• Synonyms: O-Benzyl Psilocin;4-(Benzyloxy)-3-[2-(diMethylaMino)ethyl]indole;4-(Benzyloxy)-N,N-diMethyltryptaMine;N,N-DiMethyl-4-(phenylMethoxy)-1H-indole-3-ethanaMine;2-(4-(benzyloxy)-1H-indol-3-yl)-N,N-dimethylethanamine(WXG00095)
• CAS NO: 28383-23-5
• Molecular Formula: C₁₉H₂₂N₂O
• Molecular Weight: 293.38284
• Product Categories: Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Indole Derivatives, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 28383-23-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 87-88 °C
• Boiling Point: 472.9±40.0 °C(Predicted)
• Appearance: /
• Density: 1.133±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C, Inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 17.41±0.30(Predicted)
• CAS DataBase Reference: O-Benzyl Psilocin(CAS DataBase Reference)
• NIST Chemistry Reference: O-Benzyl Psilocin(28383-23-5)
• EPA Substance Registry System: O-Benzyl Psilocin(28383-23-5)

Safety Data

• Hazardous Substances Data: 28383-23-5(Hazardous Substances Data)

Usage

Uses

Protected precursor to Psilocin.

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 20289-26-3 4-benzyloxy-1H-indole 
• 109-99-9 tetrahydrofuran 
• 52061-51-5 4-Benzyloxyindol-3-yl-N,N-dimethylglyoxylamide 
• 50-00-0 formaldehyd 
• 109249-04-9 2-(4-(benzyloxy)-1H-indol-3-yl)ethanamine 

Downstream Products

• 1640-03-5 1-benzyl-3-(2-dimethylamino-ethyl)-indol-4-ol 
• 520-52-5 psilocybin 
• 500003-04-3 [4-benzyloxy-3-(2-dimethylaminoethyl)indol-1-yl]butyric acid 
• 18483-72-2 phosphoric acid mono-[3-(2-dimethylamino-ethyl)-1-methyl-indol-4-yl ester] 
• 1465-16-3 1-methylpsilocin 
• 1640-04-6 [2-(4-benzyloxy-1-methyl-indol-3-yl)-ethyl]-dimethyl-amine 
• 879485-07-1 2-(4-(benzyloxy)-1-butyl-1H-indol-3-yl)-N,N-dimethylethan-1-amine 
• 500003-02-1 4-[4-benzyloxy-3-(2-dimethylaminoethyl)indol-1-yl]butyronitrile 
• 404888-06-8 4-benzyloxy-7-bromo-N,N-dimethyltryptamine 
• 404888-10-4 4-benzyloxy-1-tert-butoxycarbonyl-N,N-dimethyltryptamine 
• 92292-84-7 2-Acetoxy-N,N-dimethyltryptamine 
• 520-53-6 psilocin 

Relevant articles and documents

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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.

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.