Enisamium iodide

Base Information

• Chemical Name: Enisamium iodide
• CAS No.: 201349-37-3
• Molecular Formula: C₁₄H₁₅N₂O*I
• Molecular Weight: 354.19
• UNII: G22FG6Q00B
• DSSTox Substance ID: DTXSID00173960
• Wikipedia: Enisamium_iodide
• Wikidata: Q4064289
• NCI Thesaurus Code: C90783
• ChEMBL ID: CHEMBL1716983
• Mol file: 201349-37-3.mol

Synonyms:1-methyl-4-(((phenylmethyl)amino)carbonyl)-pyridinium iodide;Amizon;carbabenzpyride;enisamium iodide;N-methyl-4-benzylcarbamidopyridinium iodide

Chemical Property of Enisamium iodide

Chemical Property:

• PSA: 20.95000
• LogP: 3.22340
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 354.02291
• Heavy Atom Count: 18
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

AMIZON 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[N+]1=CC=C(C=C1)C(=O)NCC2=CC=CC=C2.[I-]
• Recent ClinicalTrials: A Clinical Study to Assess the Efficacy and Safety of Amizon? Max in the Treatment of Moderate Covid-19, Caused by the SARS-CoV-2 Virus
• Recent EU Clinical Trials: A Phase II, multicenter, multinational, randomized, double-blinded, placebo-controlled dose-finding study to evaluate the efficacy and safety of carbabenzpyride in the treatment of uncomplicated influenza A.
• Uses: 1-Methyl-4-[[(phenylmethyl)amino]carbonyl]pyridiniumiodide (CAS# 201349-37-3) is Enisamium iodide (Amizon?, Farmak) is approved for clinical use in the treatment of influenza in 11 countries which includes Ukraine, Russia, Belarus, Kazakhstan, and Uzbekistan. Enisamium iodide exhibited antiviral activity against influenza viruses in vitro, supporting the reported clinical efficacy against influenza virus infections.

Technology Process of Enisamium iodide

There total 3 articles about Enisamium iodide 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: 92.9%

isonicotinic acid benzylamide (6320-63-4) + methyl iodide (74-88-4) → N-methyl-4-benzylcarbamidopyridinium iodide (201349-37-3)

Guidance literature:

In ethanol; at 40 - 41 ℃; Product distribution / selectivity; Reflux;

Reference yield:

4-(chlorocarbonyl)pyridine (14254-57-0) → N-methyl-4-benzylcarbamidopyridinium iodide (201349-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / benzene / 10 h / Heating

2: diethyl ether / 4 h / Heating

With triethylamine; In diethyl ether; benzene; 1: Acylation / 2: Alkylation;

DOI:10.1007/BF02464277

Reference yield:

pyridine-4-carboxylic acid (55-22-1) → N-methyl-4-benzylcarbamidopyridinium iodide (201349-37-3)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / 2 h / Heating

2: triethylamine / benzene / 10 h / Heating

3: diethyl ether / 4 h / Heating

With thionyl chloride; triethylamine; In diethyl ether; benzene; 1: Substitution / 2: Acylation / 3: Alkylation;

DOI:10.1007/BF02464277

upstream raw materials:

isonicotinic acid benzylamide

methyl iodide

pyridine-4-carboxylic acid

4-(chlorocarbonyl)pyridine

Refernces

• 1、 -. "α-CRYSTALLINE FORM OF CARBABENZPYRIDE". Page/Page column 13-15. . Retrieved 2012/01/06.
• 2、 Bukhtiarova,Trinus,Danilenko,Danilenko,Ovrutskii,Sharykina. "Structure and antiinflammatory activity of isonicotinic and nicotinic amides". . p. 597 - 599. Retrieved 2007/10/03.