Tocainide
Title: Tocainide
CAS Registry Number: 41708-72-9
CAS Name: 2-Amino-N-(2,6-dimethylphenyl)propanamide
Additional Names: 2-aminopropiono-2¢,6¢-xylidide
Molecular Formula: C11H16N2O
Molecular Weight: 192.26
Percent Composition: C 68.72%, H 8.39%, N 14.57%, O 8.32%
Literature References: Anti-arrhythmic agent related to lidocaine, q.v. Prepn: R. N. Boys et al., DE 2235745 (1973 to Astra), C.A. 78, 140411 (1973); and resolution of isomers: E. W. Byrnes et al., J. Med. Chem. 22, 1171 (1979). In vitro effects on muscle contractions: R. Dengler, R. Rüdel, Arzneim.-Forsch. 29, 270 (1979). Inhibition of leucocyte locomotion in dogs: G. J. Stewart et al., Lab. Invest. 42, 302 (1980). Biotransformation in humans: A. T. Elvin et al., J. Pharm. Sci. 69, 47 (1980). Kinetics: C. Groffner, Clin. Pharmacol. Ther. 27, 64 (1980). Use in refractory ventricular arrhythmias: D. M. Roden et al., Am. Heart J. 100, 15 (1980). HPLC resolution of enantiomers: K. M. McErlane, G. K. Pillai, J. Chromatogr. 274, 129 (1983); determn in plasma: A. J. Sedman, J. Gal, ibid. 306, 155 (1984). Pharmacokinetics of enantiomers: A. H. Thomson et al., Br. J. Pharmacol. 21, 149 (1986). In vitro and in vivo pharmacodynamics of enantiomers: A. J. Block et al., J. Cardiovasc. Pharmacol. 11, 216 (1988). Review of pharmacology and therapeutic efficacy: B. Holmes et al., Drugs 26, 93-123 (1983); D. M. Roden, R. L. Woosley, N. Engl. J. Med. 315, 41-45 (1986).
 
Derivative Type: (±)-Form hydrochloride
CAS Registry Number: 71395-14-7
Manufacturers' Codes: W-36095
Trademarks: Taquidil (Roemmers); Tonocard (Astra); Xylotocan (Astra)
Molecular Formula: C11H16N2O.HCl
Molecular Weight: 228.72
Percent Composition: C 57.76%, H 7.49%, N 12.25%, O 7.00%, Cl 15.50%
Properties: Crystals from ethanol/ether, mp 246-247°.
Melting point: mp 246-247°
 
Derivative Type: R-(-)-Form hydrochloride
CAS Registry Number: 53984-74-0
Properties: Crystals from ethanol-diethyl ether, mp 265-266°. [a]D -42.16° (c = 2.63 in methanol).
Melting point: mp 265-266°
Optical Rotation: [a]D -42.16° (c = 2.63 in methanol)
 
Derivative Type: S-(+)-Form hydrochloride
CAS Registry Number: 53984-76-2
Properties: Crystals from ethanol-diethyl ether, mp 264.5°. [a]D +42.35° (c = 2.63 in methanol).
Melting point: mp 264.5°
Optical Rotation: [a]D +42.35° (c = 2.63 in methanol)
 
Therap-Cat: Antiarrhythmic (class IB).
Keywords: Antiarrhythmic.

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