baeocystin

Base Information

• Chemical Name: baeocystin
• CAS No.: 21420-58-6
• Deprecated CAS: 11044-29-4
• Molecular Formula: C₁₁H₁₅N₂O₄P
• Molecular Weight: 270.225
• UNII: 22KW205WF2
• DSSTox Substance ID: DTXSID70175693
• Nikkaji Number: J227.499J
• Wikipedia: Baeocystin
• Wikidata: Q419475
• Metabolomics Workbench ID: 115860
• ChEMBL ID: CHEMBL4634002
• Mol file: 21420-58-6.mol

Synonyms:1H-Indol-4-ol,3-[2-(methylamino)ethyl]-, dihydrogen phosphate (ester) (9CI); Indol-4-ol, 3-[2-(methylamino)ethyl]-,dihydrogen phosphate (ester) (8CI); Baeocystin; Beocystin

Chemical Property of baeocystin

Chemical Property:

• Vapor Pressure: 2.04E-12mmHg at 25°C
• Melting Point: 254-258 °C (decomp)
• Boiling Point: 538.2°Cat760mmHg
• PKA: 1.35±0.30(Predicted)
• Flash Point: 279.3°C
• Density: 1.447g/cm³
• Storage Temp.: 4°C, Hygroscopic
• Solubility.: DMSO (Slightly, Heated, Sonicated), Water (Slightly)
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 270.07694396
• Heavy Atom Count: 18
• Complexity: 322

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNCCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
• Uses: Baeocystin is an analogue of Psilocybin (P839650), a major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being Psilocin. Psychomimetic.Controlled substance (hallucinogen).

Technology Process of baeocystin

There total 21 articles about baeocystin 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: 70.0%

3-((3-(2-(benzyl(methyl)amino)ethyl)-1H-indol-4-yl)oxy)-1,5-dihydrobenzo[e][1,3,2]dioxaphosphepine 3-oxide → [3-(2-methylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate (21420-58-6,11044-29-4)

Guidance literature:

3-((3-(2-(benzyl(methyl)amino)ethyl)-1H-indol-4-yl)oxy)-1,5-dihydrobenzo[e][1,3,2]dioxaphosphepine 3-oxide; With 20% palladium hydroxide-activated charcoal; hydrogen; In methanol; for 17h; under 760.051 Torr;

With hydrogenchloride; 20% palladium hydroxide-activated charcoal; In methanol; water; for 24h;

DOI:10.1021/acs.jnatprod.9b01061

Reference yield:

3-(2-chloro-2-oxoacetyl)-1H-indol-4-yl acetate (952006-34-7) → C18H21N2O4P + [3-(2-methylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate (21420-58-6,11044-29-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Sealed tube

1.2: 0 - 20 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / 2-methyltetrahydrofuran; diethyl ether / 1 h / 0 - 78 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: 0.5 h / 0 - 20 °C / Inert atmosphere

4.1: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 17 h

With lithium aluminium tetrahydride; 20% palladium hydroxide-activated charcoal; hydrogen; sodium hydride; In tetrahydrofuran; 2-methyltetrahydrofuran; methanol; diethyl ether;

DOI:10.1021/acs.jnatprod.9b01061

Reference yield:

3-(2-(benzyl(methyl)amino)-2-oxoacetyl)-1H-indol-4-yl acetate → C18H21N2O4P + [3-(2-methylaminoethyl)-1H-indol-4-yl] dihydrogen phosphate (21420-58-6,11044-29-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / 2-methyltetrahydrofuran; diethyl ether / 1 h / 0 - 78 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 17 h

With lithium aluminium tetrahydride; 20% palladium hydroxide-activated charcoal; hydrogen; sodium hydride; In tetrahydrofuran; 2-methyltetrahydrofuran; methanol; diethyl ether;

DOI:10.1021/acs.jnatprod.9b01061

upstream raw materials:

Phosphoric acid dibenzyl ester 3-(2-methylamino-ethyl)-1H-indol-4-yl ester

3-[2-(methylamino)ethyl]-1H-indol-4-ol

4-benzyloxy-1H-indole

3-nitro-o-cresol

Refernces

• 1、 Blei, Felix,Baldeweg, Florian,Fricke, Janis,Hoffmeister, Dirk. "Biocatalytic Production of Psilocybin and Derivatives in Tryptophan Synthase-Enhanced Reactions". . p. 10028 - 10031. Retrieved 2018/07/29.