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Lidocaine hydrochloride
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73-78-9 Usage

General

Lidocaine hydrochloride was synthesized by L?fgren and Lundquist in 1943, and was clinically introduced in 1948. It remains one of the most widely used local anaesthetics. It can be administered parenterally for a peripheral nerve block (PNB), intravenously, or applied topically at strengths of 2–4%. The addition of epinephrine 1:200 000 to 1:100 000 slows the vascular absorption of lidocaine and prolongs its effects.

Physical and chemical properties

Lidocaine hydrochloride is white and odorless crystal with bitter and numb taste. It is easily soluble in water, ethanol and organic solvents, but insoluble in ether. Aqueous solution in the case of acid and alkali do not break down, repeated autoclave rarely go bad.

Local anesthetic and antiarrhythmic drugs

Lidocaine hydrochloride is a local anesthetic and antiarrhythmic drug. It is clinically used for infiltration anesthesia, epidural anesthesia, surface anesthesia (including in the thoracoscopy or abdominal surgery for mucosal anesthesia) and nerve conduction block. The drug can also be used for acute myocardial infarction after ventricular premature beats and ventricular tachycardia, and for digitalis poisoning, cardiac surgery and ventricular arrhythmias caused by cardiac catheterization. But it is usually ineffective for supraventricular arrhythmias. Lidocaine hydrochloride is an amide local anesthetic. After blood absorption or intravenous administration, the drug has obvious excitement and inhibition of biphasic effects for the central nervous system, and no excitement of the pioneer. With the dose increased, the role or toxicity increased, there is an anti-convulsive effect with sub-poisoning plasma concentration; Blood concentration of more than 5μg ? ml-1 can occur convulsions. Lidocaine hydrochloride in low doses can promote outflow of K+ in cardiomyocytes, reduce myocardial autonomy, and has antiarrhythmic effects. In the treatment dose, lidocaine hydrochloride has no significant effect for the electrical activity of cardiomyocytes, atrioventricular conduction and myocardial contraction. Increased plasma concentration may cause slowing of heart conduction, atrioventricular block, inhibition of myocardial contractility and decreased cardiac output.

Application

Lidocaine hydrochloride is characterized by strong penetration, strong dispersion, rapidly onset. The anesthetic performance is twice that of procaine and the toxicity is1. There is an anesthetic effect after 5 minutes treatments, and anesthesia can last 1 to 1.5 hours, 50% longer than procaine. The drug is effective on the heart of the disease or arrhythmia caused by cardiac glycoside, but on the supraventricular tachycardia is poor. This product is fast and oral ineffective, with short duration, and often used as intravenous administration.

Metabolism

Lidocaine is metabolized by the liver with only a small amount (3%) found unchanged in urine. The three main mechanisms of metabolism are shown below: N-de-ethylation > monoethylglycinexylidide (MEGX) > glycinexylidide Hydrolysis of glycinexylidide 5-hydroxylation of lidocaine’s benzene ring Lidocaine possesses convulsant activity. Hepatic disease or reduced hepatic blood flow (as in congestive cardiac failure) will lower metabolic capacity.

Indications

The drug can be used for infiltration anesthesia, epidural anesthesia, surface anesthesia and nerve conduction block The drug can be used for acute myocardial infarction after ventricular premature beats and ventricular tachycardia, and for digitalis poisoning, cardiac surgery and ventricular arrhythmias caused by cardiac catheterization. But it is usually ineffective for supraventricular arrhythmias.

Usage and dosage

Surface anesthesia with solution of 2% to 5%.Infiltration anesthesia with solution of 0.25% to 0.5%, conduction anesthesia with 2%, each injection point, horse, cattle 8 to 12 ml, sheep 3 to 4 ml. Epidural anesthesia with 2% solution, horse, cow, 8 to 12 ml, dog, cat, 0.22 ml per kilogram of body weight. Subcutaneous injection with 2% solution, pig, sheep, 80 ml, horse, cow, 400 ml, dog,25 ml, cat, 8.5 ml. Treatment of arrhythmia, intravenous injection: Per kg of dog’s body weight of the initial dose is 2 to 4 mg, followed by 25 to 75 micrograms per minute intravenous infusion; Cat initial dose of 250 to 500 micrograms, followed by intravenous infusion of 20 micrograms per minute.

Adverse effect

The incidence of adverse effect with lidocaine hydrochloride was about 6.3%. Most adverse effects are dose dependent. Adverse effects are drowsiness, dizziness, nausea, vomiting, burnout, euphoria, insanity, muscle convulsions, syncope, blurred vision, confusion and difficulty breathing. Large doses lead to severe sinus bradycardia, cardiac arrest, severe atrioventricular block and weakened myocardial contractility, reduced blood pressure and so on. Excess concentrations of lidocaine hydrochloride in the blood cause some problems. For example, atrial conduction slows, atrioventricular blocks (A-V-B), and inhibits myocardial contractility and cardiac output decreases. There are little allergic effects, such as erythema rash, angioneurotic edema and so on.

Additional information

Lidocaine is contraindicated in patients with known hypersensitivity to local anaesthetics of the amide type and in patients with porphyria. Reactions due to overdose with lidocaine (high plasma levels) are systemic and involve the central nervous and cardiovascular systems. Effects include medullary depression, tonic and clonic convulsions, and cardiovascular collapse Solutions in multidose vials may contain hydrobenzoate derivatives and have been associated with allergic reactions in some patients. As with all of the amide local anaesthetics protein binding is reduced in the neonate (50% versus 64% in the adult), which necessitates reduced doses if adverse reactions are to be avoided.

Medicine interactions

Cimetidine and β-blockers can inhibit metabolism of lidocaine through liver, so that the blood concentration increases and adverse reactions occur in the heart and nervous system. We should adjust the dose of lidocaine hydrochloride. Barbiturates can promote the metabolism of lidocaine hydrochloride, and the two drugs can cause bradycardia and sinus arrest. Combined with procainamide, the drug can produce excessive delirium and hallucinations, but does not affect the product plasma concentration. Isoprenaline Isoprinosine could increase the total clearance of lidocaine hydrochloride through increased liver blood flow; norepinephrine could reduce the total clearance of lidocaine hydrochlor through reduced liver blood flow. The drug is contraindicated with phenobarbital, thiopental sodium, sodium nitroprusside, mannitol, amphotericin B, ampicillin, and sulfadiazine.

Precautions

Patients Allergic to other local anesthetics may be allergic to lidocaine hydrochloride. The following circumstances with caution: Pregnancy, neonatal especially in premature infants, liver blood flow reduction, liver and kidney dysfunction, congestive heart failure, severe myocardial damage, low blood volume, shock and other patients. Strictly grasp the concentration and total medication, excessive can cause convulsions and cardiac arrest; the body metabolism is slower than procaine, and there is accumulation, causing poisoning and convulsions. Medication of the elderly should be adjusted the dose according to the needs and tolerability, and over the age of 70 should be halved. Prevent straying into the blood vessels when anaesthetizing, prevent local anesthetic poisoning. ?We should pay attention to monitoring blood pressure, electrocardiogram, and with rescue equipment when arrhythmia Treatment; drug administration should be immediately discontinued in some circumstances. For example, ECG P-R interval prolongs or QRS wave widens, other arrhythmia or the original arrhythmia deteriorates.

References

https://www.drugbank.ca/drugs/DB00281 https://en.wikipedia.org/wiki/Lidocaine

Chemical Properties

White to Off-White Solid

Originator

Xylocaine,Astra,US,1949

Uses

Apply to affected site 5 to 10 minutes before procedure. Duration of anesthesia is relatively short (<1 hour).

Uses

Local anesthesic;Na+ channel blocker

Uses

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

Definition

ChEBI: The anhydrous form of the hydrochloride salt of lidocaine.

Manufacturing Process

One mol of 2,6-xylidine is dissolved in 800 ml glacial acetic acid. The mixture is cooled to 10°C, after which 1.1 mol chloracetyl chloride is added at one time. The mixture is stirred vigorously during a few moments after which 1,000 ml half-saturated sodium acetate solution, or other buffering or alkalizing substance, is added at one time. The reaction mixture is shaken during half an hour. The precipitate formed which consists of ω-chloro-2,6- dimethyl-acetanilide is filtered off, washed with water and dried. The product is sufficiently pure for further treatment. The yield amounts to 70 to 80% of the theoretical amount.One mole of the chloracetyl xylidide thus prepared and 2.5 to 3 mols diethyl amine are dissolved in 1,000 ml dry benzene. The mixture is refluxed for 4 to 5 hours. The separated diethyl amine hydrochloride is filtered off. The benzene solution is shaken out two times with 3N hydrochloric acid, the first time with 800 ml and the second time with 400 ml acid. To the combined acid extracts is added an approximately 30% solution of sodium hydroxide until the precipitate does not increase.The precipitate, which sometimes is an oil, is taken up in ether. The ether solution is dried with anhydrous potassium carbonate after which the ether is driven off. The remaining crude substance is purified by vacuum distillation. During the distillation practically the entire quantity of the substance is carried over within a temperature interval of 1° to 2°C. The yield approaches the theoretical amount. MP 68° to 69°C. BP 180° to 182°C at 4 mm Hg; 159° to 160°C at 2 mm Hg. (Procedure is from US Patent 2,441,498.)

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).

Therapeutic Function

Local anesthetic, Antiarrhythmic

Biological Functions

Lidocaine hydrochloride (Xylocaine) is the most commonly used local anesthetic. It is well tolerated, and in addition to its use in infiltration and regional nerve blocks, it is commonly used for spinal and topical anesthesia and as an antiarrhythmic agent. Lidocaine has a more rapidly occurring, more intense, and more prolonged duration of action than does procaine.

General Description

Lidocaine hydrochloride,2-(diethylamino)-2 ,6 -acetoxylidide monohydrochloride(Xylocaine), was conceived as a derivative of gramine(3-dimethylaminomethylindole) and introduced as a localanesthetic. It is now being used intravenously as a standardparenteral agent for suppression of arrhythmias associatedwith acute myocardial infarction and cardiac surgery.It isthe drug of choice for the parenteral treatment of prematureventricular contractions.

Clinical Use

Lidocaine hydrochloride is a class IB antiarrhythmicagent with a different effect on the electrophysiologicalproperties of myocardial cells from that of procainamideand quinidine. It binds with equal affinity to the active (A)and inactive (I) Na+ ion channels. It depresses diastolic depolarizationand automaticity in the Purkinje fiber networkand increases the functional refractory period relative toaction potential duration, as do procainamide and quinidine.It differs from the latter two drugs, however, in that it doesnot decrease, and may even enhance, conduction velocity and increase membrane responsiveness to stimulation.There are fewer data available on the subcellular mechanismsresponsible for the antiarrhythmic actions of lidocainethan on the more established drug quinidine. It has been proposedthat lidocaine has little effect on membrane cation exchangeof the atria. Sodium ion entrance into ventricularcells during excitation is not influenced by lidocaine becauseit does not alter conduction velocity in this area.Lidocaine hydrochloride does depress Na+ influx duringdiastole, as do all other antiarrhythmic drugs, to diminishautomaticity in myocardial tissue. It also alters membraneresponsiveness in Purkinje fibers, allowing increased conductionvelocity and ample membrane potential at the timeof excitation.

Safety Profile

Poison by ingestion, intraperitoneal, intravenous, subcutaneous, intramuscular, and intratracheal routes. Human systemic effects: somnolence, respiratory depression, low blood pressure, cardiomyopathy includmg infarction, pulse rate increase. An experimental teratogen. Other experimental reproductive effects. A skin and eye irritant. An anesthetic. When heated to decomposition it emits very toxic fumes of NOx and HCl.

General

Lidocaine hydrochloride was synthesized by L?fgren and Lundquist in 1943, and was clinically introduced in 1948. It remains one of the most widely used local anaesthetics. It can be administered parenterally for a peripheral nerve block (PNB), intravenously, or applied topically at strengths of 2–4%. The addition of epinephrine 1:200 000 to 1:100 000 slows the vascular absorption of lidocaine and prolongs its effects.

Physical and chemical properties

Lidocaine hydrochloride is white and odorless crystal with bitter and numb taste. It is easily soluble in water, ethanol and organic solvents, but insoluble in ether. Aqueous solution in the case of acid and alkali do not break down, repeated autoclave rarely go bad.

Local anesthetic and antiarrhythmic drugs

Lidocaine hydrochloride is a local anesthetic and antiarrhythmic drug. It is clinically used for infiltration anesthesia, epidural anesthesia, surface anesthesia (including in the thoracoscopy or abdominal surgery for mucosal anesthesia) and nerve conduction block. The drug can also be used for acute myocardial infarction after ventricular premature beats and ventricular tachycardia, and for digitalis poisoning, cardiac surgery and ventricular arrhythmias caused by cardiac catheterization. But it is usually ineffective for supraventricular arrhythmias. Lidocaine hydrochloride is an amide local anesthetic. After blood absorption or intravenous administration, the drug has obvious excitement and inhibition of biphasic effects for the central nervous system, and no excitement of the pioneer. With the dose increased, the role or toxicity increased, there is an anti-convulsive effect with sub-poisoning plasma concentration; Blood concentration of more than 5μg ? ml-1 can occur convulsions. Lidocaine hydrochloride in low doses can promote outflow of K+ in cardiomyocytes, reduce myocardial autonomy, and has antiarrhythmic effects. In the treatment dose, lidocaine hydrochloride has no significant effect for the electrical activity of cardiomyocytes, atrioventricular conduction and myocardial contraction. Increased plasma concentration may cause slowing of heart conduction, atrioventricular block, inhibition of myocardial contractility and decreased cardiac output.

Application

Lidocaine hydrochloride is characterized by strong penetration, strong dispersion, rapidly onset. The anesthetic performance is twice that of procaine and the toxicity is1. There is an anesthetic effect after 5 minutes treatments, and anesthesia can last 1 to 1.5 hours, 50% longer than procaine. The drug is effective on the heart of the disease or arrhythmia caused by cardiac glycoside, but on the supraventricular tachycardia is poor. This product is fast and oral ineffective, with short duration, and often used as intravenous administration.

Metabolism

Lidocaine is metabolized by the liver with only a small amount (3%) found unchanged in urine. The three main mechanisms of metabolism are shown below: N-de-ethylation > monoethylglycinexylidide (MEGX) > glycinexylidide Hydrolysis of glycinexylidide 5-hydroxylation of lidocaine’s benzene ring Lidocaine possesses convulsant activity. Hepatic disease or reduced hepatic blood flow (as in congestive cardiac failure) will lower metabolic capacity.

Indications

The drug can be used for infiltration anesthesia, epidural anesthesia, surface anesthesia and nerve conduction block The drug can be used for acute myocardial infarction after ventricular premature beats and ventricular tachycardia, and for digitalis poisoning, cardiac surgery and ventricular arrhythmias caused by cardiac catheterization. But it is usually ineffective for supraventricular arrhythmias.

Usage and dosage

Surface anesthesia with solution of 2% to 5%.Infiltration anesthesia with solution of 0.25% to 0.5%, conduction anesthesia with 2%, each injection point, horse, cattle 8 to 12 ml, sheep 3 to 4 ml. Epidural anesthesia with 2% solution, horse, cow, 8 to 12 ml, dog, cat, 0.22 ml per kilogram of body weight. Subcutaneous injection with 2% solution, pig, sheep, 80 ml, horse, cow, 400 ml, dog,25 ml, cat, 8.5 ml. Treatment of arrhythmia, intravenous injection: Per kg of dog’s body weight of the initial dose is 2 to 4 mg, followed by 25 to 75 micrograms per minute intravenous infusion; Cat initial dose of 250 to 500 micrograms, followed by intravenous infusion of 20 micrograms per minute.

Adverse effect

The incidence of adverse effect with lidocaine hydrochloride was about 6.3%. Most adverse effects are dose dependent. Adverse effects are drowsiness, dizziness, nausea, vomiting, burnout, euphoria, insanity, muscle convulsions, syncope, blurred vision, confusion and difficulty breathing. Large doses lead to severe sinus bradycardia, cardiac arrest, severe atrioventricular block and weakened myocardial contractility, reduced blood pressure and so on. Excess concentrations of lidocaine hydrochloride in the blood cause some problems. For example, atrial conduction slows, atrioventricular blocks (A-V-B), and inhibits myocardial contractility and cardiac output decreases. There are little allergic effects, such as erythema rash, angioneurotic edema and so on.

Additional information

Lidocaine is contraindicated in patients with known hypersensitivity to local anaesthetics of the amide type and in patients with porphyria. Reactions due to overdose with lidocaine (high plasma levels) are systemic and involve the central nervous and cardiovascular systems. Effects include medullary depression, tonic and clonic convulsions, and cardiovascular collapse Solutions in multidose vials may contain hydrobenzoate derivatives and have been associated with allergic reactions in some patients. As with all of the amide local anaesthetics protein binding is reduced in the neonate (50% versus 64% in the adult), which necessitates reduced doses if adverse reactions are to be avoided.

Medicine interactions

Cimetidine and β-blockers can inhibit metabolism of lidocaine through liver, so that the blood concentration increases and adverse reactions occur in the heart and nervous system. We should adjust the dose of lidocaine hydrochloride. Barbiturates can promote the metabolism of lidocaine hydrochloride, and the two drugs can cause bradycardia and sinus arrest. Combined with procainamide, the drug can produce excessive delirium and hallucinations, but does not affect the product plasma concentration. Isoprenaline Isoprinosine could increase the total clearance of lidocaine hydrochloride through increased liver blood flow; norepinephrine could reduce the total clearance of lidocaine hydrochlor through reduced liver blood flow. The drug is contraindicated with phenobarbital, thiopental sodium, sodium nitroprusside, mannitol, amphotericin B, ampicillin, and sulfadiazine.

Precautions

Patients Allergic to other local anesthetics may be allergic to lidocaine hydrochloride. The following circumstances with caution: Pregnancy, neonatal especially in premature infants, liver blood flow reduction, liver and kidney dysfunction, congestive heart failure, severe myocardial damage, low blood volume, shock and other patients. Strictly grasp the concentration and total medication, excessive can cause convulsions and cardiac arrest; the body metabolism is slower than procaine, and there is accumulation, causing poisoning and convulsions. Medication of the elderly should be adjusted the dose according to the needs and tolerability, and over the age of 70 should be halved. Prevent straying into the blood vessels when anaesthetizing, prevent local anesthetic poisoning. ?We should pay attention to monitoring blood pressure, electrocardiogram, and with rescue equipment when arrhythmia Treatment; drug administration should be immediately discontinued in some circumstances. For example, ECG P-R interval prolongs or QRS wave widens, other arrhythmia or the original arrhythmia deteriorates.

References

https://www.drugbank.ca/drugs/DB00281 https://en.wikipedia.org/wiki/Lidocaine

Chemical Properties

White to Off-White Solid

Originator

Xylocaine,Astra,US,1949

Uses

Apply to affected site 5 to 10 minutes before procedure. Duration of anesthesia is relatively short (<1 hour).

Uses

Local anesthesic;Na+ channel blocker

Uses

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

Definition

ChEBI: The anhydrous form of the hydrochloride salt of lidocaine.

Manufacturing Process

One mol of 2,6-xylidine is dissolved in 800 ml glacial acetic acid. The mixture is cooled to 10°C, after which 1.1 mol chloracetyl chloride is added at one time. The mixture is stirred vigorously during a few moments after which 1,000 ml half-saturated sodium acetate solution, or other buffering or alkalizing substance, is added at one time. The reaction mixture is shaken during half an hour. The precipitate formed which consists of ω-chloro-2,6- dimethyl-acetanilide is filtered off, washed with water and dried. The product is sufficiently pure for further treatment. The yield amounts to 70 to 80% of the theoretical amount.One mole of the chloracetyl xylidide thus prepared and 2.5 to 3 mols diethyl amine are dissolved in 1,000 ml dry benzene. The mixture is refluxed for 4 to 5 hours. The separated diethyl amine hydrochloride is filtered off. The benzene solution is shaken out two times with 3N hydrochloric acid, the first time with 800 ml and the second time with 400 ml acid. To the combined acid extracts is added an approximately 30% solution of sodium hydroxide until the precipitate does not increase.The precipitate, which sometimes is an oil, is taken up in ether. The ether solution is dried with anhydrous potassium carbonate after which the ether is driven off. The remaining crude substance is purified by vacuum distillation. During the distillation practically the entire quantity of the substance is carried over within a temperature interval of 1° to 2°C. The yield approaches the theoretical amount. MP 68° to 69°C. BP 180° to 182°C at 4 mm Hg; 159° to 160°C at 2 mm Hg. (Procedure is from US Patent 2,441,498.)

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).

Therapeutic Function

Local anesthetic, Antiarrhythmic

Biological Functions

Lidocaine hydrochloride (Xylocaine) is the most commonly used local anesthetic. It is well tolerated, and in addition to its use in infiltration and regional nerve blocks, it is commonly used for spinal and topical anesthesia and as an antiarrhythmic agent. Lidocaine has a more rapidly occurring, more intense, and more prolonged duration of action than does procaine.

General Description

Lidocaine hydrochloride,2-(diethylamino)-2 ,6 -acetoxylidide monohydrochloride(Xylocaine), was conceived as a derivative of gramine(3-dimethylaminomethylindole) and introduced as a localanesthetic. It is now being used intravenously as a standardparenteral agent for suppression of arrhythmias associatedwith acute myocardial infarction and cardiac surgery.It isthe drug of choice for the parenteral treatment of prematureventricular contractions.

Clinical Use

Lidocaine hydrochloride is a class IB antiarrhythmicagent with a different effect on the electrophysiologicalproperties of myocardial cells from that of procainamideand quinidine. It binds with equal affinity to the active (A)and inactive (I) Na+ ion channels. It depresses diastolic depolarizationand automaticity in the Purkinje fiber networkand increases the functional refractory period relative toaction potential duration, as do procainamide and quinidine.It differs from the latter two drugs, however, in that it doesnot decrease, and may even enhance, conduction velocity and increase membrane responsiveness to stimulation.There are fewer data available on the subcellular mechanismsresponsible for the antiarrhythmic actions of lidocainethan on the more established drug quinidine. It has been proposedthat lidocaine has little effect on membrane cation exchangeof the atria. Sodium ion entrance into ventricularcells during excitation is not influenced by lidocaine becauseit does not alter conduction velocity in this area.Lidocaine hydrochloride does depress Na+ influx duringdiastole, as do all other antiarrhythmic drugs, to diminishautomaticity in myocardial tissue. It also alters membraneresponsiveness in Purkinje fibers, allowing increased conductionvelocity and ample membrane potential at the timeof excitation.

Safety Profile

Poison by ingestion, intraperitoneal, intravenous, subcutaneous, intramuscular, and intratracheal routes. Human systemic effects: somnolence, respiratory depression, low blood pressure, cardiomyopathy includmg infarction, pulse rate increase. An experimental teratogen. Other experimental reproductive effects. A skin and eye irritant. An anesthetic. When heated to decomposition it emits very toxic fumes of NOx and HCl.
InChI:InChI=1/C14H22N2O.ClH/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

73-78-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name lidocaine hydrochloride

1.2 Other means of identification

Product number -
Other names LIDOCAINE HCL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:73-78-9 SDS

73-78-9Synthetic route

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide
137-58-6

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether100%
With hydrogenchloride; pyrographite In water; 1,2-dichloro-ethane for 0.333333h; pH=3.5; pH-value;88.72%
With hydrogenchloride In water; acetone at 20℃; pH=<= 4;80.6%
diethylamine
109-89-7

diethylamine

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

Conditions
ConditionsYield
Stage #1: chloroacetyl chloride; 2,6-dimethylaniline In 1-methyl-pyrrolidin-2-one; methanol; water at 120℃; for 0.306667h; Flow reactor;
Stage #2: diethylamine With potassium hydroxide In methanol; water at 130℃; under 12751.3 Torr; for 0.295h; Flow reactor;
Stage #3: With hydrogenchloride In methanol; diethyl ether; water
2.6-dimethylphenol
576-26-1

2.6-dimethylphenol

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium hydroxide; 2,6-dimethylcyclohexanone; 5%-palladium/activated carbon / 5 h / 180 °C
2: sodium methylate / 0.5 h / 95 °C
3: hydrogenchloride; pyrographite / 1,2-dichloro-ethane; water / 0.33 h / pH 3.5
View Scheme
2,6-dimethylaniline
87-62-7

2,6-dimethylaniline

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / acetone / 3 h / 20 °C
2: acetone / 8 h / Reflux
3: hydrogenchloride / water; acetone / 20 °C / pH <= 4
View Scheme
saccharin sodium salt
128-44-9

saccharin sodium salt

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium benzo[d]isothiazol-3-olate 1,1-dioxide

2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium benzo[d]isothiazol-3-olate 1,1-dioxide

Conditions
ConditionsYield
In acetonitrile at 50℃; for 4h; Sonication;99%
potassium acesulfame
55589-62-3

potassium acesulfame

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium 6-methyl-1,2,3-oxathiazin-4-olate 2,2-dioxide

2-((2,6-dimethylphenyl)amino)-N,N-diethyl-2-oxoethan-1-aminium 6-methyl-1,2,3-oxathiazin-4-olate 2,2-dioxide

Conditions
ConditionsYield
In acetonitrile at 50℃; for 4h; Sonication;98%
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

sodium vanillate

sodium vanillate

lidocaine vanillate

lidocaine vanillate

Conditions
ConditionsYield
In methanol; water at 50℃; for 4h;97%
sodium mono-glycyrrhizinate

sodium mono-glycyrrhizinate

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

lidocaine mono-glycyrrhizinate

lidocaine mono-glycyrrhizinate

Conditions
ConditionsYield
In methanol; water at 50℃; for 4h;96%
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

1-ethyl-2-methyl-3-(2,6-dimethylphenyl)imidazolidin-4-one
32845-42-4

1-ethyl-2-methyl-3-(2,6-dimethylphenyl)imidazolidin-4-one

Conditions
ConditionsYield
With glucose dehydrogenase; D-glucose; cytochrome P450BM3 R47L/Y51F/A191T/N239H/I259V/A276T/A330W/L353I mutant; oxygen; β-nicotinamide adenine dinucleotide phosphate sodium salt In ethanol at 25℃; for 2h; pH=8.5; Enzymatic reaction;95%
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 80 percent / CH2Cl2; acetonitrile / 3 h / 20 °C
View Scheme
Cs(1+)*C36H83B10S(1-)

Cs(1+)*C36H83B10S(1-)

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

C36H83B10S(1-)*C14H22N2O*H(1+)

C36H83B10S(1-)*C14H22N2O*H(1+)

Conditions
ConditionsYield
In dichloromethane; water for 2h; Sonication;95%
carbon dioxide
124-38-9

carbon dioxide

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

lidocainium hydrocarbonate

lidocainium hydrocarbonate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water at -4 - 0℃; under 760.051 Torr;93%
sodium salicylate
54-21-7

sodium salicylate

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

lidocaine monosalicylic acid salt

lidocaine monosalicylic acid salt

Conditions
ConditionsYield
In water; acetone at 20℃;87%
In water; acetone at 20℃;87%
In water; acetone at 20℃; Product distribution / selectivity;54%
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

N-(2,6-dimethylphenyl)-2-ethylaminoacetamide
7728-40-7

N-(2,6-dimethylphenyl)-2-ethylaminoacetamide

Conditions
ConditionsYield
With glucose dehydrogenase; D-glucose; cytochrome P450BM3 R47L/Y51F/F81W/F87V/E267V/I401P mutant; β-nicotinamide adenine dinucleotide phosphate sodium salt In ethanol at 25℃; for 2h; pH=8.5; Enzymatic reaction;85%
With 1H-imidazole; dihydrogen peroxide; chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III) In dichloromethane; acetonitrile55%
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

aspirin
50-78-2

aspirin

lidocainium acetylsalicylate
1220976-13-5

lidocainium acetylsalicylate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone at 0℃;83%
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

sodium 2-(4-isobutylphenyl)propionate
31121-93-4

sodium 2-(4-isobutylphenyl)propionate

lidocainium ibuprofenate
1158170-79-6

lidocainium ibuprofenate

Conditions
ConditionsYield
In water at 20℃; for 4h;75.7%
potassium thioacyanate
333-20-0

potassium thioacyanate

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

[Ni(lidocaine)2(thiocyanate)2]

[Ni(lidocaine)2(thiocyanate)2]

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 4h; pH=7;72.5%
nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

sodium dicyanamide
1934-75-4

sodium dicyanamide

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

[Ni(lidocaine)2(dicyanamide)2]

[Ni(lidocaine)2(dicyanamide)2]

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 4h; pH=7;68%
potassium thioacyanate
333-20-0

potassium thioacyanate

cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

[Co(lidocaine)2(thiocyanate)2]

[Co(lidocaine)2(thiocyanate)2]

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 4h; pH=7;65.6%
cobalt(II) diacetate tetrahydrate
6147-53-1

cobalt(II) diacetate tetrahydrate

sodium dicyanamide
1934-75-4

sodium dicyanamide

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

[Co(lidocaine)2(dicyanamide)2]

[Co(lidocaine)2(dicyanamide)2]

Conditions
ConditionsYield
With triethylamine In methanol; water at 20℃; for 4h; pH=7;62%
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

N-(2,6-Dimethyl-phenyl)-2-[(E)-ethylimino]-acetamide

N-(2,6-Dimethyl-phenyl)-2-[(E)-ethylimino]-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 80 percent / iodosylbenzene, imidazole / chloroiron(III) / CH2Cl2; acetonitrile / 3 h / 20 °C
View Scheme
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

1-(2,6-dimethylphenyl)-3,5-dihydroxypyrrolidin-2-one

1-(2,6-dimethylphenyl)-3,5-dihydroxypyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 1.) iodosylbenzene, imidazole / 1.) chloroiron(III) / 1.) CH2Cl2, CH3CN, 20 deg C, 3 h, 2.) RT, 3 h
View Scheme
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

2-(N-ethylacetamido)2',6'-dimethylacetanilide

2-(N-ethylacetamido)2',6'-dimethylacetanilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 86 percent / CH2Cl2 / 2 h / 20 °C
View Scheme
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

3-(2,6-dimethylphenyl)-1-ethyl-α-hydroxy-2',6'-dimethyl-4-oxoimidazolidine-2-propanilide

3-(2,6-dimethylphenyl)-1-ethyl-α-hydroxy-2',6'-dimethyl-4-oxoimidazolidine-2-propanilide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 55 percent / H2O2, imidazole / chloromanganese(III) / CH2Cl2; acetonitrile
2: 18 percent / iodosylbenzene, imidazole / chloroiron(III) / CH2Cl2; acetonitrile / 3 h / 20 °C
View Scheme
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

sodium docusate
577-11-7

sodium docusate

lidocainium docusate

lidocainium docusate

Conditions
ConditionsYield
In methanol for 2h;
In ethanol; dichloromethane at 50℃; Inert atmosphere;
dihydrogen hexachloroplatinate

dihydrogen hexachloroplatinate

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

lignocaine hydrochloride platinum complex

lignocaine hydrochloride platinum complex

Conditions
ConditionsYield
In ethanol ligand added to soln. of Pt-compound; heated at 60-80°C for ca. 30 min;; filtration; washing (EtOH then ether); drying (vacuum); recrystn. (EtOH) by slow cooling and evapn.;
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

acrylic acid
79-10-7

acrylic acid

3C3H4O2*ClH*C14H22N2O

3C3H4O2*ClH*C14H22N2O

Conditions
ConditionsYield
at 80℃;
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

A

N-(2,6-dimethylphenyl)-2-ethylaminoacetamide
7728-40-7

N-(2,6-dimethylphenyl)-2-ethylaminoacetamide

B

1-ethyl-2-methyl-3-(2,6-dimethylphenyl)imidazolidin-4-one
32845-42-4

1-ethyl-2-methyl-3-(2,6-dimethylphenyl)imidazolidin-4-one

Conditions
ConditionsYield
With glucose dehydrogenase; D-glucose; cytochrome P450BM3 R47L/Y51F/F87V/E267V/I401P mutant; β-nicotinamide adenine dinucleotide phosphate sodium salt In ethanol at 25℃; for 2h; pH=8.5; Enzymatic reaction;
C62H68N16O24S4(4-)*4Na(1+)

C62H68N16O24S4(4-)*4Na(1+)

lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

C14H22N2O*ClH*C62H68N16O24S4(4-)*4Na(1+)

C14H22N2O*ClH*C62H68N16O24S4(4-)*4Na(1+)

Conditions
ConditionsYield
In aq. phosphate buffer pH=7.4; UV-irradiation;
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

C14H22N2O(18)O

C14H22N2O(18)O

Conditions
ConditionsYield
With hydrogen (18)O-peroxide In water for 0.0166667h;
lidocaine hydrochloride
73-78-9

lidocaine hydrochloride

lidocaine N-oxide
2903-45-9

lidocaine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In water for 0.0166667h;

73-78-9Upstream product

73-78-9Downstream Products

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