Pilsicainide hydrochloride

Base Information

• Chemical Name: Pilsicainide hydrochloride
• CAS No.: 88069-49-2
• Molecular Formula: C17H24N2O.HCl
• Molecular Weight: 308.851
• Hs Code.: 2933990090
• European Community (EC) Number: 835-741-6
• UNII: 03C8I9296V
• DSSTox Substance ID: DTXSID7057860
• Wikidata: Q27247552
• ChEMBL ID: CHEMBL4303511
• Mol file: 88069-49-2.mol

Synonyms:1H-pyrrolizine-7a(5H)-acetamide, N-(2,6-dimethylphenyl)tetrahydro-, hydrochloride (1:1);1H-pyrrolizine-7a(5H)-acetamide, N-(2,6-dimethylphenyl)tetrahydro-, hydrochloride hemihydrate;N-(2,6-dimethylphenyl)-8-pyrrolizidineacetamide hydrochloride;pilsicainide;pilsicainide hydrochloride;pilsicainide hydrochloride hemihydrate;pilsicainide hydrochloride hydrate;SUN 1165;SUN-1165;tetrahydro-1H-pyrrolizine-7a(5H)-aceto-2',6'-xylidide

Chemical Property of Pilsicainide hydrochloride

Chemical Property:

• Vapor Pressure: 3.7E-07mmHg at 25°C
• Melting Point: 212-214°
• Boiling Point: 416.9 °C at 760 mmHg
• Flash Point: 205.9 °C
• PSA: 32.34000
• LogP: 3.27130
• Storage Temp.: room temp
• Solubility.: Chloroform (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 308.1655411
• Heavy Atom Count: 21
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

Pilsicainide Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C)NC(=O)CC23CCCN2CCC3.Cl
• Description: Pilsicainide hydrochloride is a new pynolizidine lidocaine derivative with antiarrhythmic activity. It is the first pharmaceutical product introduced by Suntory and was solely developed in Japan. The compound is reported to be highly effective in the treatment of premature ventricular contraction. It has no anticholinergic or CNS activity and is not as likely as other class 1C antiarrhythmics to have restricted indications.
• Uses: Pilsicainide hydrochloride has been used as a sodium channel blocker:to study its effects on electrophysiological parameters in guinea pig pulmonary vein preparationto study its effects on Ca2+?release and arrhythmic events in Andersen-Tawil syndrome induced pluripotent stem cells (ATS-iPSC)-derived cardiomyocytesto study its electrophysiological effects on the guinea pig atrium

Technology Process of Pilsicainide hydrochloride

There total 6 articles about Pilsicainide hydrochloride 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: 82.0%

C18H24N2O3 → Pilsicainide hydrochloride (88069-49-2)

Guidance literature:

C₁₈H₂₄N₂O₃; In toluene; at 60 - 65 ℃; for 2h; Large scale;

With hydrogenchloride; In ethanol; water; for 0.5h; pH=2 - 3; Large scale;

Reference yield:

tetrahydro-1H-pyrrolizidine-7a(5H)-acetic acid hydrochloride + 2,6-dimethylaniline (87-62-7) → Pilsicainide hydrochloride (88069-49-2)

Guidance literature:

tetrahydro-1H-pyrrolizidine-7a(5H)-acetic acid hydrochloride; 2,6-dimethylaniline; With trichlorophosphate; In chloroform; at 0 - 20 ℃; for 1h;

With sodium hydroxide; In water; at 20 ℃; pH=12 - 13;

With hydrogenchloride; In methanol; water; at 20 ℃; for 1h;

Reference yield:

2,6-dimethylaniline (87-62-7) → Pilsicainide hydrochloride (88069-49-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N,N-dimethyl-formamide / 12 h / Reflux; Large scale

2.1: ammonia; ammonium hydroxide / methanol / 15 h / -5 - 18 °C / Large scale

3.1: potassium hydroxide; water; methanol / 6 h / 50 °C / Large scale

4.1: toluene / 2 h / 60 - 65 °C / Large scale

4.2: 0.5 h / pH 2 - 3 / Large scale

With methanol; ammonium hydroxide; ammonia; water; potassium hydroxide; In methanol; N,N-dimethyl-formamide; toluene;

upstream raw materials:

ethyl 3-((2,6-dimethylphenyl)amino)-3-oxopropanoate

2,6-dimethylaniline

2-cyano-N-(2,6-dimethyl-phenyl)-acetamide

Downstream raw materials:

N-(2,6-dimethyl-3-nitrophenyl)-2-(hexahydropyrrolizin-7a-yl)acetamide

3-aminopilsicainide

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