Normethadone

Base Information

• Chemical Name: Normethadone
• CAS No.: 467-85-6
• Molecular Formula: C20H25 N O
• Molecular Weight: 295.425
• European Community (EC) Number: 207-401-1
• NSC Number: 19598
• UNII: KR2L2A68XL
• DSSTox Substance ID: DTXSID6057748
• Nikkaji Number: J5.915C
• Wikipedia: Normethadone
• Wikidata: Q1218578
• NCI Thesaurus Code: C76843
• Metabolomics Workbench ID: 152741
• ChEMBL ID: CHEMBL346331
• Mol file: 467-85-6.mol

Synonyms:6-dimethylamino-4,4-diphenylhexan-3-one;nor-methadone;normethadone;normethadone hydrochloride

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Chemical Property of Normethadone

Chemical Property:

• Vapor Pressure: 4.31E-07mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 414.8°Cat760mmHg
• PKA: pKa 6.00(50% aq EtOH) (Uncertain)
• Flash Point: 123.6°C
• Density: 1.02g/cm³
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 295.193614421
• Heavy Atom Count: 22
• Complexity: 320

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)C(CCN(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

Technology Process of Normethadone

There total 11 articles about Normethadone 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: 59.0%

4-dimethylamino-2,2-diphenyl-butyronitrile (23278-88-8) + ethylmagnesium bromide (925-90-6) → normethadone (467-85-6)

Guidance literature:

In diethyl ether; toluene; at 0 - 110 ℃; for 3h;

DOI:10.1021/acs.jmedchem.1c00611

Reference yield:

Diphenylacetonitrile (86-29-3) + ethylmagnesium bromide (925-90-6) → normethadone (467-85-6)

Guidance literature:

DOI:10.1021/ja01181a023 DOI:10.1021/ja01142a510

Reference yield:

4-bromo-2,2-diphenylbutyronitrile (39186-58-8) → normethadone (467-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / acetonitrile / 130 °C / Sealed tube

2: toluene; diethyl ether / 3 h / 0 - 110 °C

With potassium carbonate; In diethyl ether; toluene; acetonitrile; 2: |Grignard Reaction;

DOI:10.1021/acs.jmedchem.1c00611

upstream raw materials:

4-dimethylamino-2,2-diphenyl-butyronitrile

ethylmagnesium bromide

1,1-diphenylbutan-2-one

2-(dimethylamino)ethyl chloride

Downstream raw materials:

trimethyl-(4-oxo-3,3-diphenyl-hexyl)-ammonium; iodide

6-dimethylamino-4,4-diphenyl-hexan-3-ol

Refernces

• 1、 Bonifazi, Alessandro,Battiti, Francisco O.,Sanchez, Julie,Zaidi, Saheem A.,Bow, Eric,Makarova, Mariia,Cao, Jianjing,Shaik, Anver Basha,Sulima, Agnieszka,Rice, Kenner C.,Katritch, Vsevolod,Canals, Meritxell,Lane, J. Robert,Newman, Amy Hauck. "Novel Dual-Target μ-Opioid Receptor and Dopamine D3Receptor Ligands as Potential Nonaddictive Pharmacotherapeutics for Pain Management". . p. 7778 - 7808. Retrieved 2021/06/27.