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Merck

A5513

Sigma-Aldrich

N-Acetylprocainamide hydrochloride

≥99% (HPLC), powder

Synonym(s):

N-Acetylnovocainamide hydrochloride, Acecainide hydrochloride, NAPA

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About This Item

Linear Formula:
4-(CH3CONH)C6H4CONHCH2CH2N(C2H5)2·HCl
CAS Number:
Molecular Weight:
313.82
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.77

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Quality Level

Assay

≥99% (HPLC)

form

powder

mp

184-186 °C (lit.)

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

Cl[H].CCN(CC)CCNC(=O)c1ccc(NC(C)=O)cc1

InChI

1S/C15H23N3O2.ClH/c1-4-18(5-2)11-10-16-15(20)13-6-8-14(9-7-13)17-12(3)19;/h6-9H,4-5,10-11H2,1-3H3,(H,16,20)(H,17,19);1H

InChI key

IYEWBJUCJHKLHD-UHFFFAOYSA-N

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Application

N-Acetylprocainamide hydrochloride may be used:
  • as an internal standard for spiking plasma samples for ultra-high-pressure liquid chromatography coupled with a diode array detector (UHPLC-DAD) analysis[1]
  • to test its relaxant effect on tracheal smooth muscle tissue preparations[2]
  • in preparation of complexes with N-acetyl-L-tyrosine methyl ester and N-acetyl-L-phenylalanine methyl ester for studying intermolecular interactions using nuclear magnetic resonance (NMR) spectroscopy studies[3]

N-Acetylprocainamide hydrochloride is a class III antiarrhythmic compound. N-Acetylprocainamide hydrochloride has been used in a study to determine the disposition of procainamide and N-acetylprocainamide in protein-calorie malnutrition. N-Acetylprocainamide hydrochloride has also been used to study pharmacokinetics of procainamide and N-acetylprocainamide in rats.

Biochem/physiol Actions

N-acetyltransferase II in liver catalyzes the conversion of procainamide to N-acetylprocainamide (NAPA).[1]
Class III antiarrhythmic. Increases the duration of the action potential by decreasing the delayed outward potassium current, slightly decreasing the calcium current, and slightly depressing the inward rectifier potassium current. This is the active metabolite of procainamide that does not induce systemic lupus erythematosus.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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D Jung et al.
Drug metabolism and disposition: the biological fate of chemicals, 13(3), 359-363 (1985-05-01)
The influence of dietary protein deficiency on the disposition of procainamide (PA) and its major metabolite, N-acetylprocainamide (NAPA) was investigated in male Sprague-Dawley rats fed for 4 weeks on a 23 (control) or a 5% (low) protein diet ad libitum.
The evidence for complex formation between N-acetyl-l-tyrosine methyl ester and N-acetylprocainamide hydrochloride using NMR spectroscopy
Janik A, et al.
Structural Chemistry, 20(4), 699-707 (2009)
B L Kamath et al.
Journal of pharmaceutical sciences, 70(3), 299-302 (1981-03-01)
The pharmacokinetics of distribution and elimination of procainamide and its major metabolite, N-actylprocainamide, were studied in rats. Eight rats were selected randomly, and each received intravenously 14C-labeled procainamide hydrochloride (75 mg/kg) or 14C-labeled N-acetylprocainamide hydrochloride (86 mg/kg) according to a
Anusha Balla et al.
Pharmaceutics, 10(2) (2018-03-31)
A simple, sensitive, and reliable reversed-phase, Ultra-High-Pressure Liquid Chromatography (UHPLC) coupled with a Diode Array Detector (DAD) method for the simultaneous determination of Procainamide (PA) and its major metabolite, N-acetylprocainamide (NAPA), in rat plasma was developed and validated. A simple
Y L He et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 13(3), 303-308 (2001-06-01)
The dosage regimen of a drug eliminated predominantly through the kidney need to be adjusted for the patients with renal disease. The objective of the present study was to establish a quantitative approach to precisely predicting the renal clearances of

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