Tocainide

Base Information

• Chemical Name: Tocainide
• CAS No.: 41708-72-9
• Molecular Formula: C11H16 N2 O
• Molecular Weight: 192.261
• Hs Code.: 2924299090
• European Community (EC) Number: 255-505-0
• UNII: 27DXO59SAN
• DSSTox Substance ID: DTXSID9040766
• Nikkaji Number: J16.873D
• Wikipedia: Tocainide
• Wikidata: Q757058
• NCI Thesaurus Code: C66607
• Pharos Ligand ID: B6BRQG6J9VF5
• Metabolomics Workbench ID: 43294
• ChEMBL ID: CHEMBL1762
• Mol file: 41708-72-9.mol

Synonyms:Hydrochloride, Tocainide;Tocainide;Tocainide Hydrochloride;Tocainide Monohdyrochloride, (R)-Isomer;Tocainide Monohydrobromide, (R)-Isomer;Tocainide Monohydrochloride;Tocainide Monohydrochloride, (+-)-Isomer;Tocainide Monohydrochloride, (S)-Isomer;Tocainide, (+-)-Isomer;Tocainide, (R)-Isomer;Tocainide, (S)-Isomer;Tonocard;W 36095;W-36095;W36095;Xylotocan

Chemical Property of Tocainide

Chemical Property:

• Melting Point: 246-266 °C
• Refractive Index: 1.5750 (estimate)
• Boiling Point: 328.25°C (rough estimate)
• PKA: pKa 7.75(H2O t = 25.0±0.2 I = 0.01 (NaCl)) (Uncertain)
• PSA: 55.12000
• Density: 1.0529 (rough estimate)
• LogP: 2.36240
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 192.126263138
• Heavy Atom Count: 14
• Complexity: 196

Purity/Quality:

95-99% ^*data from raw suppliers

Tocainide 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)NC(=O)C(C)N
• Uses: Tocainide is used for suppressing symptoms of ventricular arrhythmia and tachycardia, and for premature cardiac contractions.
• Therapeutic Function: Antiarrhythmic
• Clinical Use: Tocainide (Tonocard) is an orally effective antiarrhythmic agent with close structural similarities to lidocaine. Tocainide is indicated for the treatment of symptomatic ventricular arrhythmias refractory to more conventional therapy. Serious noncardiac adverse effects limit its use to patients with life-threatening arrhythmias.
• Drug interactions: When used with other class IB antiarrhythmic drugs, tocainide toxicity may be increased without significant gain in antiarrhythmic efficacy.

Technology Process of Tocainide

There total 5 articles about Tocainide 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:

α-bromopropionyl-2,6-dimethylaniline (41708-73-0) → tocainide (41708-72-9,76213-25-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / dimethylformamide / 2 h / Heating

2: 1.) N₂H₄*H₂O, 2.) conc. HCl / 1.) aq. EtOH, reflux, 2.) aq. EtOH, reflux, 30 min

With hydrogenchloride; hydrazine hydrate; In N,N-dimethyl-formamide;

DOI:10.1021/jm00139a007

Reference yield:

[(2,6-dimethylphenyl)aminocarbonyl-1-ethyl]chloride (36292-29-2) → tocainide (41708-72-9,76213-25-7)

Guidance literature:

With potassium iodide; ammonia; In ethanol;

Reference yield:

concd. ammonia + 2-iodo-2',6'-propionoxylidide (76213-24-6) → tocainide (41708-72-9,76213-25-7)

Guidance literature:

upstream raw materials:

2-phthalimidopropiono-2',6'-xylidide

α-bromopropionyl-2,6-dimethylaniline

2-iodo-2',6'-propionoxylidide

[(2,6-dimethylphenyl)aminocarbonyl-1-ethyl]chloride

Downstream raw materials:

N-(2,6-dimethylphenyl)-2-[(naphthalen-1-ylmethyl)amino]propanamide

N-(2,6-dimethylphenyl)-2-[(naphthalen-2-ylmethyl)amino]propanamide

(+)-Tocainide

(-)-Tocainide

Refernces

• 1、 -. "Primary aminoacylanilides, methods of making the same and use as antiarrhythmic drugs". . . Retrieved 2008/06/13.