6169. Mexiletine

Nomenclature

CAS number: 31828-71-4
1-(2,6-Dimethylphenoxy)-2-propanamine; 1-(2,6-xylyloxy)-2-propylamine; 1-(2′,6′-dimethylphenoxy)-2-aminopropane; 1-methyl-2-(2,6-xylyloxy)ethylamine.
C11H17NO; mol wt 179.26.
C 73.70%, H 9.56%, N 7.81%, O 8.93%.

Description and references

Orally active class Ib antiarrhythmic agent; blocks the voltage-dependent fast sodium channel. Prepn: FR 1551055; H. Kppe et al., US 3954872 (1968, 1976 both to Boehringer, Ing.). Stereospecific synthesis: A. Carocci et al., Tetrahedron: Asymmetry 11, 3619 (2000). Pharmacology: B. N. Singh, E. M. Vaughan Williams, Br. J. Pharmacol. 44, 1 (1972); J. D. Allen et al., ibid. 45, 561 (1972). Characterization of metabolites by mass spec and 13C-NMR: K. N. Scott et al., Drug Metab. Dispos. 1, 506 (1973). Toxicological study: A. Kast et al., Iyakuhin Kenkyu 13, 922 (1982), C.A. 97, 192878q (1982). GC-MS determn in serum: A. Dasgupta, O. Yousef, J. Chromatogr. B 705, 283 (1998). Comprehensive description: M. A. Abounassif et al., Anal. Profiles Drug Subs. 20, 433-474 (1991). Review of pharmacology and clinical efficacy in arrhythmia: C. Y. C. Chew et al., Drugs 17, 161-181 (1979); in diabetic neuropathy: B. Jarvis, A. J. Coukell, ibid. 56, 691-707 (1998). Review of clinical pharmacokinetics: L. Labbé, J. Turgeon, Clin. Pharmacokinet. 37, 361-384 (1999).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 5370-01-4
Ko-1173; Mexitil (Boehringer, Ing.); Ritalmex (Valeant).
C11H17NO.HCl; mol wt 215.72.
C 61.24%, H 8.41%, N 6.49%, O 7.42%, Cl 16.43%.

Properties

White to off-white crystals from ethanol-ether, mp 203-205°. pKa: 9.0. Slightly bitter taste. Freely sol in water, alcohol; slightly sol in acetonitrile. Practically insol in ether. LD50 in male, female rats, mice, rabbits (mg/kg): 350, 400, 310, 400, 180, 160 orally; in male, female rats, mice (mg/kg): 27, 30, 43, 50 i.v. (Kast).

Therapeutic Category

Antiarrhythmic (class IB).

Therapeutic Category (Veterinary)

Antiarrhythmic (class IB).

Keywords

Antiarrhythmic