Structural Formula Vector Image
Title: Lidocaine
CAS Registry Number: 137-58-6
CAS Name: 2-(Diethylamino)-N-(2,6-dimethylphenyl)acetamide
Additional Names: 2-diethylamino-2¢,6¢-acetoxylidide; w-diethylamino-2,6-dimethylacetanilide; lignocaine
Trademarks: Cuivasil (IDC); Lidoderm (Hind); LidoPosterine (Kade); Vagisil (Combe)
Molecular Formula: C14H22N2O
Molecular Weight: 234.34
Percent Composition: C 71.75%, H 9.46%, N 11.95%, O 6.83%
Literature References: Long-acting, membrane stabilizing agent against ventricular arrhythmia. Originally developed as a local anesthetic. Prepn: N. M. Löfgren, B. J. Lundqvist, US 2441498 (1948 to Astra); A. D. H. Self, A. P. T. Easson, GB 706409 (1954 to May & Baker); I. P. S. Hardie, E. S. Stern, GB 758224 (1956 to J. F. Macfarlane & Co.); Zhuravlev, Nikolaev, Zh. Obshch. Khim. 30, 1155 (1960). Toxicity studies: E. R. Smith, B. R. Duce, J. Pharmacol. Exp. Ther. 179, 580 (1971); G. H. Kronberg et al., J. Med. Chem. 16, 739 (1973). Review of pharmacokinetics: N. L. Benowitz, W. Meister, Clin. Pharmacokinet. 3, 177 (1978). Review of action as local anesthetic: Löfgren, Studies on Local Anesthetics: Xylocaine, A New Synthetic Drug (Hoeggstroms, Stockholm, 1948); Cooper, Pharm. J. 171, 68 (1953). Reviews of anti-arrhythmic agents: J. L. Anderson et al., Drugs 15, 271 (1978); L. H. Opie, Lancet 1, 861 (1980); E. Carmeliet, Ann. N.Y. Acad. Sci. 427, 1 (1984). Comprehensive description: K. Groningsson et al., Anal. Profiles Drug Subs. 14, 207-243 (1985); M. F. Powell, ibid. 15, 761-779 (1986). Review of use in treatment of postherpetic neuralgia: P. S. Davies, B. S. Galer, Drugs 64, 937-947 (2004).
Properties: Needles from benzene or alcohol, mp 68-69°. bp4 180-182°; bp2 159-160°. Insol in water. Sol in alcohol, ether, benzene, chloroform, oils. Partition coefficient (octanol/water, pH 7.4): 43.
Melting point: mp 68-69°
Boiling point: bp4 180-182°; bp2 159-160°
Log P: Partition coefficient (octanol/water, pH 7.4): 43
Derivative Type: Hydrochloride
CAS Registry Number: 73-78-9; 6108-05-0 (monohydrate)
Trademarks: Basicaina (Galenica); Batixim (So.Se.); Dynexan (Kreussler); Heweneural (Hevert); Licain (DeltaSelect); Lidesthesin (Ritsert); Lidofast (Angelini); Lidoject (Hexal); Lidrian (Baxter); Odontalg (Giovanardi); Sedagul (Wild); Xylocaine (AstraZeneca); Xylocard (AstraZeneca); Xylocitin (Jenapharm); Xyloneural (Strathmann)
Molecular Formula: C14H22N2O.HCl
Molecular Weight: 270.80
Percent Composition: C 62.09%, H 8.56%, N 10.34%, O 5.91%, Cl 13.09%
Properties: Crystals, mp 127-129°; monohydrate, mp 77-78°. Very sol in water, alcohol; sol in chloroform. Insol in ether. pH of 0.5% aq soln: 4.0-5.5. LD50 in mice (mg/kg): 292 orally (Smith, Duce); 105 i.p.; 19.5 i.v. (Kronberg).
Melting point: mp 127-129°; mp 77-78°
Toxicity data: LD50 in mice (mg/kg): 292 orally (Smith, Duce); 105 i.p.; 19.5 i.v. (Kronberg)
Therap-Cat: Anesthetic (local); antiarrhythmic (class IB).
Therap-Cat-Vet: Anesthetic (local).
Keywords: Anesthetic (Local); Antiarrhythmic.

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