O-Benzyl Psilocin

Base Information

• Chemical Name: O-Benzyl Psilocin
• CAS No.: 28383-23-5
• Molecular Formula: C19H21N2O
• Molecular Weight: 294.396
• ChEMBL ID: CHEMBL5028661
• DSSTox Substance ID: DTXSID60543983
• Nikkaji Number: J1.156.117I
• Wikidata: Q82420955
• Mol file: 28383-23-5.mol

Synonyms:O-Benzyl Psilocin;28383-23-5;N,N-dimethyl-2-(4-phenylmethoxy-1H-indol-3-yl)ethanamine;2-[4-(Benzyloxy)-3-indolyl]-N,N-dimethylethanamine;CHEMBL5028661;SCHEMBL12558834;DTXSID60543983;4-benzyloxy-n,n-dimethyltryptamine;BDBM596382;US11591353, Compound I-46;SY351182;F15300;N, N-dimethyl-2-(4-phenylmethoxy-1H-indol-3-yl)ethanamine;2-[4-(Benzyloxy)-1H-indol-3-yl]-N,N-dimethylethan-1-amine;2-(4-(benzyloxy)- 1H-indol-3- yl)-N,N- bis(methyl- d3)ethan-1- amine- 1,1,2,2-d4

Chemical Property of O-Benzyl Psilocin

Chemical Property:

• Melting Point: 87-88 °C
• Boiling Point: 472.9±40.0 °C(Predicted)
• PKA: 17.41±0.30(Predicted)
• PSA: 28.26000
• Density: 1.133±0.06 g/cm3(Predicted)
• LogP: 3.85100
• Storage Temp.: -20°C, Inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 294.173213330
• Heavy Atom Count: 22
• Complexity: 327

Purity/Quality:

97% ^*data from raw suppliers

O-BenzylPsilocin 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC1=CNC2=C1C(=CC=C2)OCC3=CC=CC=C3
• Uses: Protected precursor to Psilocin.

Technology Process of O-Benzyl Psilocin

There total 7 articles about O-Benzyl Psilocin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-(4-(benzyloxy)-1H-indol-3-yl)ethanamine (109249-04-9) → 2-(4-(benzyloxy)-1H-indol-3-yl)-N,N-dimethylethan-1-amine (28383-23-5)

Guidance literature:

With sodium cyanoborohydride; In methanol; acetic acid; at 20 ℃; for 3h;

Reference yield: 94.8%

4-Benzyloxyindol-3-yl-N,N-dimethylglyoxylamide (52061-51-5) → 2-(4-(benzyloxy)-1H-indol-3-yl)-N,N-dimethylethan-1-amine (28383-23-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; 1,4-dioxane; 1.) 4 h, 2.) reflux, 20 h;

DOI:10.1055/s-1999-3490

Reference yield: 61.0%

2-(N,N-dimethylamino)ethanol (108-01-0) + 4-benzyloxy-1H-indole (20289-26-3) → 2-(4-(benzyloxy)-1H-indol-3-yl)-N,N-dimethylethan-1-amine (28383-23-5)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; caesium carbonate; at 150 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.tet.2016.03.007

upstream raw materials:

4-Benzyloxyindol-3-yl-N,N-dimethylglyoxylamide

formaldehyd

2-(4-(benzyloxy)-1H-indol-3-yl)ethanamine

tetrahydrofuran

Downstream raw materials:

[2-(1-acetyl-4-benzyloxy-indol-3-yl)-ethyl]-dimethyl-amine

psilocin

[2-(4-benzyloxy-1-methyl-indol-3-yl)-ethyl]-dimethyl-amine

2-Acetoxy-N,N-dimethyltryptamine