Encainide

Encainide (trade name Enkaid) is a class Ic antiarrhythmic agent. It is no longer used because of its frequent proarrhythmic side effects.[1]

Encainide
Clinical data
Trade namesEnkaid
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa605040
ATC code
Legal status
Legal status
  • Withdrawn
Identifiers
IUPAC name
  • 4-Methoxy-N-[2-(1-methyl-2-piperidin-1-ylethyl)phenyl]benzamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H28N2O2
Molar mass352.478 g·mol−1
3D model (JSmol)
SMILES
  • COc1ccc(C(=O)Nc2ccccc2CCC2CCCCN2C)cc1
InChI
  • InChI=1S/C22H28N2O2/c1-24-16-6-5-8-19(24)13-10-17-7-3-4-9-21(17)23-22(25)18-11-14-20(26-2)15-12-18/h3-4,7,9,11-12,14-15,19H,5-6,8,10,13,16H2,1-2H3,(H,23,25) Y
  • Key:PJWPNDMDCLXCOM-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Synthesis
Synthesis:[2][3][4]

The condensation of 2-picoline [109-06-8] (1) with 2-nitrobenzaldehyde [552-89-6] (2) catalyzed with acetic anhydride gives 2-[2-(2-nitrophenyl)ethenyl]pyridine, CID:142706 {aka 2-(o-nitrostyryl)pyridine} [77340-84-2] (3). N-Methylation followed by the reduction the aromaticity in the pyridine ring as well as the nitro group to the corresponding aniline gives 2-(2-aminophenethyl)-1-methylpiperidine aka 2-[2-(1-methylpiperidin-2-yl)ethyl]aniline, [37611-80-6] CID:11085282 (4). Amide formation with p-anisoyl chloride [100-07-2] (5) completed the synthesis of Encainide (6).

See also

References
  1. Echt DS, Liebson PR, Mitchell LB, Peters RW, Obias-Manno D, Barker AH, et al. (March 1991). "Mortality and morbidity in patients receiving encainide, flecainide, or placebo. The Cardiac Arrhythmia Suppression Trial". The New England Journal of Medicine. 324 (12): 781–8. doi:10.1056/NEJM199103213241201. PMID 1900101.
  2. Dykstra SJ, Minielli JL, Lawson JE, Ferguson HC, Dungan KW (September 1973). "Lysergic acid and quinidine analogs. 2-(o-Acylaminophenethyl)piperidines". Journal of Medicinal Chemistry. 16 (9): 1015–20. doi:10.1021/jm00267a012. PMID 4745503.
  3. DE 2210154, Dykstra SJ, Minelli JL, issued 1972
  4. US 3931195, Dykstra SJ, Minelli JL, issued 1976
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