Psilocybine

Base Information

• Chemical Name: Psilocybine
• CAS No.: 520-52-5
• Molecular Formula: C12H17 N2 O4 P
• Molecular Weight: 284.252
• European Community (EC) Number: 208-294-4
• UNII: 2RV7212BP0
• DSSTox Substance ID: DTXSID0048898
• Nikkaji Number: J6.604D
• Wikipedia: Psilocybin
• Wikidata: Q208118
• NCI Thesaurus Code: C62529
• Pharos Ligand ID: CPRUAYCGFSPW
• Metabolomics Workbench ID: 53398
• ChEMBL ID: CHEMBL194378
• Mol file: 520-52-5.mol

Synonyms:Psilocibin;Psilocybin;Psilocybine

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Chemical Property of Psilocybine

Chemical Property:

• Vapor Pressure: 8.75E-12mmHg at 25°C
• Melting Point: 220-2280C
• Refractive Index: 1.644
• Boiling Point: 523.4°Cat760mmHg
• PKA: 1.25±0.30(Predicted)
• Flash Point: 270.4°C
• PSA: 95.60000
• Density: 1.409g/cm³
• LogP: 1.74350
• Storage Temp.: −20°C
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 284.09259403
• Heavy Atom Count: 19
• Complexity: 347

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Mushroom Toxins
• Canonical SMILES: CN(C)CCC1=CNC2=C1C(=CC=C2)OP(=O)(O)O
• Recent ClinicalTrials: Psilocybin-facilitated Treatment for Chronic Pain
• Recent EU Clinical Trials: Efficacy and safety of COMP360 psilocybin therapy in anorexia nervosa: a proof-of-concept study
• Description: The intentional ingestion of hallucinogenic mushrooms by Mesoamerican natives dates back centuries. Early European explorers documented the Mayan and Aztec symbolism depicting the use of mushroom during spiritual ceremonies. Albert Hofmann first synthesized lysergic acid diethylamide (LSD) from psilocybin extracted from mushrooms. During the 1960s and 1970s, researchers conducted experiments on the utility of psilocybin for psychotherapy before drug laws curbed its use. Psilocybin is described as an entheogen, a substance used to raise spiritual consciousness. Today most countries have outlawed psilocybin possession; however, widespread illicit use continues.
• Uses: The most common use of this mushroom is to induce recreational hallucinations. Some Native American groups continue to employ psilocybin-containing mushroom species in official ceremonies. The adjunctive use of psilocybin for mainstream psychotherapy has been discontinued. Hallucinogenic mushrooms are generally considered a low-harm drug of abuse. The major of two hallucinogenic components of Teonanacatl, the sacred mushroom of Mexico, the other component being psilocin. Psychomimetic. Controlled substance (hallucinogen).

Technology Process of Psilocybine

There total 17 articles about Psilocybine 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: 87.5%

{benzyl[2-(4-oxyindol-3-yl)ethyl]dimethylamino}-4-O-benzyl phosphate → psilocybin (520-52-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; at 20 ℃; for 3h;

Reference yield: 20.7%

7-phosphoryloxytryptamine + S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6) → psilocybin (520-52-5)

Guidance literature:

With Psilocybe cubensis enzymes PsiM; In aq. buffer; at 25 ℃; for 4h; pH=8; Enzymatic reaction;

DOI:10.1002/chem.201801047

Reference yield:

psilocin (520-53-6) → psilocybin (520-52-5)

Guidance literature:

With n-butyllithium; dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate; hydrogen; diisopropylamine; palladium on activated charcoal; Yield given; Multistep reaction; 1.) THF, hexane, -78 deg C, 3 min; 1.5 h, 2.) MeOH, 60 psig, 3 h;

DOI:10.1055/s-1999-3490

upstream raw materials:

psilocin

4-benzyloxy-1H-indole

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

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

Refernces

• 1、 Kargbo, Robert B.,Meisenheimer, Poncho,Sherwood, Alexander M.,Tarpley, Gary. "An Improved, Practical, and Scalable Five-Step Synthesis of Psilocybin". . p. 688 - 694. Retrieved 2020.
• 2、 -. "PREPARATION OF PSILOCYBIN, DIFFERENT POLYMORPHIC FORMS, INTERMEDIATES, FORMULATIONS AND THEIR USE". . . Retrieved 2019/05/02.