Psilocin

Base Information

• Chemical Name: Psilocin
• CAS No.: 520-53-6
• Molecular Formula: C12H16 N2 O
• Molecular Weight: 204.272
• Hs Code.: 2933990090
• European Community (EC) Number: 208-296-5
• UNII: CMS88KUW0G
• DSSTox Substance ID: DTXSID5048899
• Nikkaji Number: J12.982H
• Wikipedia: Psilocin
• Wikidata: Q409150
• Pharos Ligand ID: KZK9G56W64Q9
• Metabolomics Workbench ID: 49684
• ChEMBL ID: CHEMBL65547
• Mol file: 520-53-6.mol

Synonyms:(3-(2-dimethylamino)ethyl)indol-4-ol;psilocin;psilocin hydrochloride;psilocin tartrate (1:1)

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Chemical Property of Psilocin

Chemical Property:

• Vapor Pressure: 9.89E-07mmHg at 25°C
• Melting Point: 173-176°
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 392.8 °C at 760 mmHg
• PKA: 10.01±0.40(Predicted)
• Flash Point: 191.3 °C
• PSA: 39.26000
• Density: 1.178 g/cm³
• LogP: 1.97760
• Storage Temp.: −20°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 204.126263138
• Heavy Atom Count: 15
• Complexity: 208

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 36/37/39-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(C)CCC1=CNC2=C1C(=CC=C2)O
• Recent ClinicalTrials: Comparing the Effects of Psilocin and Psilocybin in Healthy Adults
• Uses: The minor hallucinogenic component of the Teonanacatl mushroom. Psilocin is the 4-hydroxy analog of Psilocybin, formed by metabolic dephosphorylation of Psilocybin and is an active neurochemical. Psychomimetic. Controlled substance (hallucinogen).

Technology Process of Psilocin

There total 22 articles about 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: 100.0%

2-(4-(benzyloxy)-1H-indol-3-yl)-N,N-dimethylethan-1-amine (28383-23-5) → psilocin (520-53-6)

Guidance literature:

With palladium 10% on activated carbon; ammonium formate; In methanol; at 70 ℃; for 0.75h; Inert atmosphere;

DOI:10.1016/j.tet.2016.03.007

Reference yield: 91.0%

2-(4-hydroxy-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide (30000-67-0) → psilocin (520-53-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; Heating;

DOI:10.3987/com-98-s(h)87

Reference yield: 87.5%

3-[2-(dimethylamino)-2-oxoacetyl]-1H-indol-4-yl acetate (30000-66-9) → psilocin (520-53-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h; Heating;

upstream raw materials:

2-(4-(benzyloxy)-1H-indol-3-yl)-N,N-dimethylethan-1-amine

3-[2-(dimethylamino)-2-oxoacetyl]-1H-indol-4-yl acetate

2-(4-hydroxy-indol-3-yl)-N,N-dimethyl-2-oxo-acetamide

O-Methylpsilocine

Downstream raw materials:

phosphoric acid dibenzyl ester

psilocybin

toluene-4-sulfonic acid-[3-(2-dimethylamino-ethyl)-indol-4-yl ester]

2-Acetoxy-N,N-dimethyltryptamine

Refernces

• 1、 -. "PREPARATION OF PSILOCYBIN, DIFFERENT POLYMORPHIC FORMS, INTERMEDIATES, FORMULATIONS AND THEIR USE". Paragraph 00237; 00326-00363. . Retrieved 2019/05/02.
• 2、 Furman, Svetlana,Nissim-Bardugo, Elinor,Zeeli, Shani,Weitman, Michal,Nudelman, Abraham,Finkin-Groner, Efrat,Moradov, Dorit,Shifrin, Helena,Schorer-Apelbaum, Donna,Weinstock, Marta. "Synthesis and in vitro evaluation of anti-inflammatory activity of ester and amine derivatives of indoline in RAW 264.7 and peritoneal macrophages". . p. 2283 - 2287. Retrieved 2014/05/20.