Lidocaine hydrochloride Chemical Properties

Melting point:

75-79℃

storage temp. 

2-8°C

solubility 

H₂O: soluble

form 

solid

color 

white

Water Solubility 

Soluble in water (50 mg/ml), chloroform, ethanol, and benzene. Insoluble in diethyl ether.

InChI

InChI=1S/C14H22N2O.ClH.H2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4;;/h7-9H,5-6,10H2,1-4H3,(H,15,17);1H;1H2

InChIKey

YECIFGHRMFEPJK-UHFFFAOYSA-N

SMILES

C1(C(C)=CC=CC=1C)NC(=O)CN(CC)CC.O.Cl

LogP

2.359 (est)

CAS DataBase Reference

6108-05-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

AN7700000

TSCA 

Yes

HazardClass 

6.1

HS Code 

2924296000

MSDS

• Language:English Provider:SigmaAldrich

Lidocaine hydrochloride Usage And Synthesis

Chemical Properties

Linocaine hydrochloride is a white or almost white, crystalline powder with slightly bitter and numbing taste. Soluble in water, ethanol and organic solvents, insoluble in ether. The aqueous solution does not decompose under acid and alkali conditions, and it rarely deteriorates after repeated autoclaving.

Uses

Linocaine hydrochloride is a fast voltage-gated sodium channel blocker that used in Local anesthesia and heart rhythm disorders. Its actions are more intense and its effects more prolonged than those of procaine but its duration of action is shorter than that of bupivacaine or prilocaine.

Definition

ChEBI: Linocaine hydrochloride is the monohydrate form of lidocaine hydrochloride. It is a local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of Procaine but its duration of action is shorter than that of bupivacaine or prilocaine.

Application

Anesthetic (local); antiarrhythmic (class IB). Long-acting, membrane stabilizing agent against ventricular arrhythmia. Originally developed as a local anesthetic.

brand name

Alpha caine Hydrochloride (Carlisle); Anestacon (Polymedica); Laryng-O-Jet (International Medication); Lidocaton (Phar maton); Lidopen (Meridian); Xylocaine (Abraxis); Xylo caine (AstraZeneca); Xylocaine (Dentsply).

Contact allergens

Linocaine hydrochloride is an anesthetic of the amide group, like articaine or bupivacaine. Immediate-type IgE-dependent reactions are rare, and delayed-type contact dermatitis is exceptional. Cross-reactivity between the different amide anesthetics is not systematic.

Synthesis

A method for preparing Lidocaine hydrochloride is described as follows. The method comprises the following steps: by taking 2,6-xylenol as a raw material, Pd/C as a primary catalyst and 2,6-dimethylcyclohexanone as a promoter, performing liquid phase amination with ammonia water at high temperature, thereby obtaining a midbody 2,6-dimethylaniline; enabling sodium methylate, 2,6-dimethylaniline and N,N-lignocaine methyl acetate as raw materials to react at 90-95 DEGC, distilling while reaction is performed to remove methanol till no methanol can be evaporated out, continuously reacting for 30 minutes, cooling to the room temperature, adding dichloroethane, washing with water, and leaving to stand to layer, thereby obtaining an organic layer, namely, a lidocaine based dichloroethane solution; further adding hydrochloric acid into the lidocaine based dichloroethane solution, adjusting the pH value to be 3.5-4 by using hydrogen chloride, adding activated carbon to reflux for 20-40 minutes, filtering, concentrating the filtrate, cooling, crystallizing, and dying, thereby obtaining Lidocaine hydrochloride.

Mode of action

Lidocaine Hydrochloride is the hydrochloride salt form of lidocaine, an aminoethylamide and a prototypical member of the amide class anesthetics. Lidocaine interacts with voltage-gated Na+ channels in the nerve cell membrane and blocks the transient increase in permeability of excitable membranes to Na+. This prevents the generation and conduction of nerve impulses and produces a reversible loss of sensation. Lidocaine hydrochloride also exhibits class IB antiarrhythmic effects. The agent decreases the flow of sodium ions into myocardial tissue, especially on the Purkinje network, during phase 0 of the action potential, thereby decreasing depolarization, automaticity and excitability.

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