67 - Lidocaine for neural blockade  pp. 279-283

Lidocaine for neural blockade

By Mary Hanna Bekhit

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Lidocaine's chemical name is 2-(diethylamino)-N-(2,6-dimethylphenyl)ethanamide (IUPAC). Its other chemical names include: N-diethylaminoacetyl-2,6,xylidine hydrochloride, 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide, 2-diethylamino-2′,6′-acetoxylidide, and omega-diethylamino-2′,6′-dimethylacetanilide.Lidocaine is also known as lignocaine (former British Approved Name).

Its proprietary names include Akten, Xylocaine, Xylotox, Leostesin, EMLA, Rucaina, Isicaine, Lidoderm, Cuivasal, Duncaine, Sylestesin, Anestacon, Gravocain, Lidothesin, Xylocitin, and Xylestesin. Lidocaine in its generic form is manufactured by many different pharmaceutical companies worldwide.

Chemical structure/properties (Figure 67.1): lidocaine's aromatic group, a benzene ring, confers its lipophilic properties, and its tertiary amine group possesses hydrophilic properties. The two groups are linked by an amide bond. Lidocaine has a molecular weight of 234 g/mol, melting point of 68°C, and a pKa of 7.9. It is usually prepared as lidocaine hydrochloride, a white, odorless, crystalline powder.

Historical development

Lidocaine is the most widely used and first synthesized amide local anesthetic. Nils Lofgren, a Swedish chemist who later became a professor of organic chemistry at the University of Stockholm, synthesized the chemical in 1943 and named it xylocaine. His coworker Bengt Lundqvist first tested the chemical on himself via injection prior to marketing the drug in 1948.

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