O-Methylpsilocin

Base Information

• Chemical Name: O-Methylpsilocin
• CAS No.: 3965-97-7
• Molecular Formula: C9H10N2S
• Molecular Weight: 218.299
• UNII: X4NBI2F334
• ChEMBL ID: CHEMBL32029
• DSSTox Substance ID: DTXSID20475892
• Wikidata: Q4637164
• Wikipedia: 4-MeO-DMT
• Mol file: 3965-97-7.mol

Synonyms:O-Methylpsilocine;4-methoxy DMT;O-Methylpsilocin;3965-97-7;2-(4-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine;4-Methoxy-N,N-dimethyltryptamine;N,N-Dimethyl-4-methoxytryptamine;CHEMBL32029;X4NBI2F334;[2-(4-methoxy-1H-indol-3-yl)ethyl]dimethylamine;1H-Indole-3-ethanamine, 4-methoxy-N,N-dimethyl-;[2-(4-Methoxy-1H-indol-3-yl)-ethyl]-dimethyl-amine;UNII-X4NBI2F334;SCHEMBL19235737;DTXSID20475892;HFYHBTWTJDAYGW-UHFFFAOYSA-N;BDBM50130292;PDSP1_000023;PDSP2_000023;PD019779;A6626;NS00018412;Q4637164

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of O-Methylpsilocin

Chemical Property:

• Melting Point: 89-92 °C
• Boiling Point: 334.475 °C at 760 mmHg
• PKA: 17.46±0.30(Predicted)
• Flash Point: 156.085 °C
• PSA: 28.26000
• Density: 1.097±0.06 g/cm3(Predicted)
• LogP: 2.28060
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 218.141913202
• Heavy Atom Count: 16
• Complexity: 220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC1=CNC2=C1C(=CC=C2)OC
• Uses: O-Methylpsilocine is a derivative of psilocin (P839630), a minor hallucinogenic component of the Psilocybin mushroom.

Technology Process of O-Methylpsilocin

There total 9 articles about O-Methylpsilocin 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: 91.0%

3-(N,N-dimethylaminocarbonylmethyl)-4-methoxyindole (52335-79-2) → O-Methylpsilocine (3965-97-7)

Guidance literature:

With lithium aluminium tetrahydride; In 1,4-dioxane; for 0.5h; Heating;

Reference yield: 61.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 4-methoxytryptamine (3610-35-3) → O-Methylpsilocine (3965-97-7)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In methanol; at 20 ℃; for 2.5h;

DOI:10.1016/j.tet.2009.09.050

Reference yield:

N-tert-butoxycarbonyl-2-iodo-3-methoxyaniline (194869-14-2) → O-Methylpsilocine (3965-97-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 271 mg / diisopropylethylamine,; benzyltriethylammonium chloride,; palladium(II) acetate / dimethylformamide / 19 h / 80 °C

2: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

3: 74 percent / acetyl chloride / methanol / 0.5 h / Heating

4: 82 percent / benzene; hexane / 0.83 h / Heating

5: 91 percent / lithium aluminum hydride / dioxane / 0.5 h / Heating

With lithium aluminium tetrahydride; N-benzyl-N,N,N-triethylammonium chloride; palladium diacetate; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; In 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Alkylation / 2: Cyclization / 3: deprotection / 4: amidation / 5: Reduction;

upstream raw materials:

(4-methoxy-indol-3-yl)-glyoxylic acid dimethylamide

3-(N,N-dimethylaminocarbonylmethyl)-4-methoxyindole

N-tert-butoxycarbonyl-2-iodo-3-methoxyaniline

methyl 2-(4-methoxy-1H-indol-3-yl)acetate

Downstream raw materials:

psilocin

Refernces

• 1、 Sakagami, Hideki,Ogasawara, Kunio. "A new synthesis of psilocin". . p. 1131 - 1135. Retrieved 2007/10/03.