N-(2,6-dimethylphenyl)-2-(hexahydro-1H-pyrrolizin-7a-yl)acetamide hydrochloride

• ChemBase ID: 154642
• Molecular Formular: C17H25ClN2O
• Molecular Mass: 308.8462
• Monoisotopic Mass: 308.16554111
• SMILES: Cc1cccc(c1NC(=O)CC12CCCN1CCC2)C.Cl
• Canonical SMILES: O=C(CC12CCCN2CCC1)Nc1c(C)cccc1C.Cl
• InChI: InChI=1S/C17H24N2O.ClH/c1-13-6-3-7-14(2)16(13)18-15(20)12-17-8-4-10-19(17)11-5-9-17;/h3,6-7H,4-5,8-12H2,1-2H3,(H,18,20);1H
• InChIKey: NZOSVDHCTCLGEB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2,6-dimethylphenyl)-2-(hexahydro-1H-pyrrolizin-7a-yl)acetamide hydrochloride
• IUPAC Traditional name: pilsicainide hydrochloride
• Synonyms: N-(2,6-Dimethylphenyl)tetrahydro-1H-pyrrolizine-7a(5H)-acetamide hydrochloride; Pilzicainide hydrochloride; SUN 1165; Pilsicainide hydrochloride

Database IDs

• MDL Number: MFCD00903769
• PubChem SID: 162248780
• PubChem CID: 114817

CALCULATED PROPERTIES

• Acid pKa: 14.4369135
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.32494128
• LogD (pH = 7.4): 0.23881635
• Log P: 3.1614408
• Molar Refractivity: 83.7736 cm^3
• Polarizability: 31.70631 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: deionized water: >5 mg/mL
• Apperance: white to beige powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H24N2O · xHCl

DETAILS

Sigma Aldrich - P0026

Biochem/physiol Actions
Pilsicainide hydrochloride is a pure sodium channel blocker and an open channel blocker of Na+1 channels. Pilsicainide was defined as a pure sodium channel blocker. The compound is classified as a class Ic antiarrhythmic drug, and was originally developed in Japan. Similar to Lidocaine, Pilsicainide binds to open channels, but slowly. Pilsicainide is capable of selectively blocking the late currents in the mutant Na(+) channels that show dominant abnormal burst openings such as in δKPQ mutants. The compound is used to induce Brugada syndrome (BS) in animal models.