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Key Documents

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P9391

Sigma-Aldrich

Procainamide hydrochloride

Synonym(s):

4-Amino-N-(2-diethylaminoethyl)benzamide hydrochloride, 4-Aminobenzoic acid 2-diethylaminoethylamide

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About This Item

Linear Formula:
H2NC6H4CONHCH2CH2N(C2H5)2·HCl
CAS Number:
614-39-1
Molecular Weight:
271.79
Beilstein:
3729517
EC Number:
210-381-7
MDL number:
MFCD00012998
UNSPSC Code:
12352200
PubChem Substance ID:
24277864

form

powder

mp

167-169 °C (lit.)

solubility

H2O: soluble
ethanol: soluble

originator

Bristol-Myers Squibb

SMILES string

Cl.CCN(CC)CCNC(=O)c1ccc(N)cc1

InChI

1S/C13H21N3O.ClH/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11;/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17);1H

InChI key

ABTXGJFUQRCPNH-UHFFFAOYSA-N

Gene Information

human ... SCN10A(6336) , SCN11A(11280) , SCN1A(6323) , SCN2A(6326) , SCN3A(6328) , SCN4A(6329) , SCN5A(6331) , SCN7A(6332) , SCN8A(6334) , SCN9A(6335)

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Biochem/physiol Actions

Inhibits DNA methyltransferase and modulates epigenetic regulation of gene expression. Na+ channel blocker and Class IA anti-arrhythmic.

Features and Benefits

This compound is a featured product for ADME Tox and Gene Regulation research. Discover more featured ADME Tox and Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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

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    Certificates of Analysis (COA)

    Lot/Batch Number
    WXBC2834V
    WXBC2443V
    MKBS4413V
    SLBG4388V
    129K1962V

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    Y H Kim et al.
    Circulation, 100(6), 666-674 (1999-08-10)
    Ventricular fibrillation (VF) is maintained by 2 mechanisms: first by reentry formation and second by spontaneous wave break or wave splitting. We hypothesized that spontaneous wave break results from a critical shortening of the action potential duration (APD) during VF
    M Odijk et al.
    Biosensors & bioelectronics, 26(4), 1521-1527 (2010-08-24)
    We have designed an integrated 3-electrode electrochemical cell on-chip with high analyte conversion rates for use in drug metabolism studies. The electrochemical cell contains platinum working and counter electrodes and an iridium oxide pseudo-reference electrode. The pseudo-reference electrode has a
    Malyaj Narwaley et al.
    Chemical research in toxicology, 24(7), 1031-1039 (2011-06-16)
    Aromatic amine drugs like aminoglutethimide (AG) and related congeners have been shown to produce phenyl radicals through metabolism by myeloperoxidase (MPO)/H(2)O(2), which has been proposed to play a role in drug-induced agranulocytosis. AG has also been shown to induce MPO
    Fei Li et al.
    Biochemical pharmacology, 83(10), 1435-1444 (2012-03-06)
    Procainamide, a type I antiarrhythmic agent, is used to treat a variety of atrial and ventricular dysrhythmias. It was reported that long-term therapy with procainamide may cause lupus erythematosus in 25-30% of patients. Interestingly, procainamide does not induce lupus erythematosus
    Ludovic Halby et al.
    Chembiochem : a European journal of chemical biology, 13(1), 157-165 (2011-12-16)
    DNA methyltransferases (DNMTs) are responsible for DNA methylation, an epigenetic modification involved in gene regulation. Families of conjugates of procainamide, an inhibitor of DNMT1, were conceived and produced by rapid synthetic pathways. Six compounds resulted in potent inhibitors of the
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