6543. Nikethamide

Nomenclature

CAS number: 59-26-7
N,N-Diethyl-3-pyridinecarboxamide; N,N-diethylnicotinamide; pyridine-3-carboxylic acid diethylamide; nicotinic acid diethylamide; Anacardone; Astrocar; Carbamidal; Cardamine; Cardiamid; Cardimon; Coracon; Coractiv N (Phyteia); Coramine (Novartis); Cordiamin; Corediol (Meiji); Cormed (Reiss); Cormid; Corvitol; Corvotone; Dynacoryl; Eucoran; Inicardio; Niamine; Nicamide; Nicor; Nicorine; Nikardin; Pyricardyl; Salvacard; Stimulin; Ventramine.
C10H14N2O; mol wt 178.23.
C 67.39%, H 7.92%, N 15.72%, O 8.98%.

Description and references

Prepd by the action of thionyl chloride on nicotinic acid, followed by treatment with diethylamine hydrochloride; also formed by heating nicotinic acid or quinolinic acid anhydride with diethylamine: Hartmann, Seiberth, US 1403117 (1922); from nicotinic acid + benzenesulfonyldiethyl amide: Oxley et al., J. Chem. Soc. 1946, 763. Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).

Chemical structure

Properties

Slightly viscous liquid or cryst solid. Faintly bitter taste followed by a faint sensation of warmth. d425 1.058-1.066 (liq). mp 24-26°. bp760 296-300° (some decompn); bp10 158-159°; bp3 128-129°; bp0.4 115°. nD20 1.525-1.526; nD25 1.522-1.524. Misc with water, ether, chloroform, acetone, alc. Usually marketed as a 25% w/v aq soln, pH 6.0-6.5. Incompatible with Na2CO3 solns which cause precipitation; tannates produce an amorph ppt. LD50 i.p. in rats: 272 mg/kg (Goldenthal).

Therapeutic Category

CNS and respiratory stimulant.

Therapeutic Category (Veterinary)

Respiratory stimulant.

Keywords

CNS Stimulant; Respiratory Stimulant