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Lidocaine

CAS No.
137-58-6
Chemical Name:
Lidocaine
Synonyms
Xylocaine;Xyline;2-(Diethylamino)-N-(2,6-dimethylphenyl)-acetamide;Anestacon;Ligoncaine;Mesocain;Xylocain;Maricaine;Xilocaina;Alphacaine
CBNumber:
CB9128024
Molecular Formula:
C14H22N2O
Molecular Weight:
234.34
MDL Number:
MFCD08443609
MOL File:
137-58-6.mol
MSDS File:
SDS
Last updated:2024-03-18 11:47:05

Lidocaine Properties

Melting point 66-69°C
Boiling point bp4 180-182°; bp2 159-160°
Density 0.9944 (rough estimate)
refractive index 1.5110 (estimate)
Flash point 9℃
storage temp. Store at RT
solubility ethanol: 4 mg/mL
pka pKa 7.88(H2O)(Approximate)
form powder
color White to slightly yellow
Water Solubility practically insoluble
Merck 14,5482
BCS Class 1
Stability Stable. Incompatible with strong oxidizing agents.
InChIKey NNJVILVZKWQKPM-UHFFFAOYSA-N
LogP 2.440
CAS DataBase Reference 137-58-6(CAS DataBase Reference)
FDA 21 CFR 310.545
EWG's Food Scores 1-3
NCI Dictionary of Cancer Terms lidocaine
FDA UNII 98PI200987
NCI Drug Dictionary Xylocaine
ATC code C01BB01,C05AD01,D04AB01,N01BB02,N01BB52,R02AD02,S01HA07,S02DA01
NIST Chemistry Reference Lidocaine(137-58-6)
EPA Substance Registry System Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)- (137-58-6)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P301+P312+P330
Hazard Codes  Xn,T,F
Risk Statements  22-39/23/24/25-23/24/25-11
Safety Statements  22-26-36-45-36/37-16-7
RIDADR  3249
WGK Germany  3
RTECS  AN7525000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29242990
Toxicity LD50 oral in rat: 317mg/kg
NFPA 704
0
2 0

Lidocaine price More Price(31)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich L1026 Lidocaine analytical standard 137-58-6 1vial $127 2024-03-01 Buy
Sigma-Aldrich L-018 Lidocaine solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 137-58-6 1mL $36.6 2024-03-01 Buy
Sigma-Aldrich 1366002 Lidocaine United States Pharmacopeia (USP) Reference Standard 137-58-6 250mg $436 2024-03-01 Buy
Sigma-Aldrich BP727 Lidocaine British Pharmacopoeia (BP) Reference Standard 137-58-6 100MG $252 2023-06-20 Buy
TCI Chemical L0156 Lidocaine >99.0%(HPLC)(T) 137-58-6 25g $54 2024-03-01 Buy
Product number Packaging Price Buy
L1026 1vial $127 Buy
L-018 1mL $36.6 Buy
1366002 250mg $436 Buy
BP727 100MG $252 Buy
L0156 25g $54 Buy

Lidocaine Chemical Properties,Uses,Production

description

Lidocaine is a local anesthetic, also known as Xylocaine, in recent years it has been replaced procaine, widely used in local infiltration anesthesia in cosmetic plastic surgery, it can block the nerve excitability and conduction by inhibiting the sodium channels of nerve cell membrane. The fat soluble and protein binding rate of lidocaine is higher than procaine, its cell penetrating ability is strong, fast onset, long duration of action, the interaction strength is 4 times of procaine.
Lidocaine is used in infiltration anesthesia, epidural anesthesia, topical anesthesia (including thoracoscopy or abdominal surgery for mucosal anesthesia) and nerve block. In order to extend the time of anesthesia, reduce the poisoning of lidocaine and other side effects, can be added in the anesthetic epinephrine.
Lidocaine can also be used for the treatment of ventricular premature beat after acute myocardial infarction, ventricular tachycardia, digitalis poisoning, cardiac surgery and cardiac catheterization-induced ventricular arrhythmias, including ventricular premature beats, ventricular tachycardia and ventricular fibrillation. Lidocaine is also used for duration status of epilepsy which other anti-seizure drugs are not effective, as well as local or spinal anesthesia. But it is usually ineffective for supraventricular arrhythmias.

Chemical property

Lidocaine is white needle like crystals, and its melting point is 68-69℃; boiling point is 180-182℃ (0.53kPa), soluble in ethanol in 159-160℃ (0.267kPa), ether, benzene, chloroform and oil, do not dissolve in water. In common use radical hydrochloride, lidocaine hydrochloride (C14H22N2O • HCL, [73-78-9]) is a white crystalline powder. Melting point 127-129℃, and the monohydrate melting point is 77-78℃. Easily soluble in water, 0.5% aqueous solution pHO 4.0-5.5. Odorless, bitter taste.

Uses

Lidocaine is an Anesthetic (local); antiarrhythmic (class IB). Long-acting, membrane stabilizing agent against ventricular arrhythmia. Originally developed as a local anesthetic. Neuroprotective & Neuroresearch Products. Lidocaine is widely used in surface anesthesia, anesthesia, conduction anesthesia and epidural anesthesia. The LD50 of oral lidocaine hydrochloride to mice was 290 mg/kg.

Description

Lidocaine [2-(diethylamino)-N-(2, 6-dimethylphenyl) acetamide monohydrochloride] is the most commonly used amino amide-type local anesthetic. Lidocaine is very lipid soluble and, thus, has a more rapid onset and a longer duration of action than most amino ester-type local anesthetics, such as procaine and tetracaine. It can be administered parenterally (with or without epinephrine) or topically either by itself or in combination with prilocaine or etidocaine as a eutectic mixture that is very popular with pediatric patients. The use of lidocaine–epinephrine mixtures should be avoided, however, in areas with limited vascular supply to prevent tissue necrosis. Lidocaine also frequently is used as a class IB antiarrhythmic agent for the treatment of ventricular arrhythmias, both because it binds and inhibits sodium channels in the cardiac muscle and because of its longer duration of action than amino ester-type local anesthetics.
Central nervous system changes are the most frequently observed systemic toxicities of lidocaine. The initial manifestations are restlessness, vertigo, tinnitus, slurred speech, and eventually, seizures. Subsequent manifestations include CNS depression with a cessation of convulsions and the onset of unconsciousness and respiratory depression or cardiac arrest. This biphasic effect occurs because local anesthetics initially block the inhibitory GABAergic pathways, resulting in stimulation, and eventually block both inhibitory and excitatory pathways (i.e., block the sodium channels associated with the NMDA receptors, resulting in overall CNS inhibition).

Chemical Properties

solid

Originator

Xylocaine,Astra,US,1949

Uses

Lidocaine is used in creams and lotions to soothe areas of inflamed skin or for example in hemorrhoid preparations to reduce discomfort; used by doctors to anesthetise areas prior to surgery, often avoiding the need for a general anesthetie; used by injection after a heart attack to treat some rhythm disturbances.

Uses

Lidocaine (Alphacaine)is a selective inverse peripheral histamine H1-receptor agonist with an IC50 of >32 μM. [1] Histamine is responsible for many features of allergic reactions. Lidocaine (Alphacaine)is a second-generation antihistamine agent closely st

Uses

Antiarrhythmic Agents, Anesthetics;Anticonvulsant;antihypertensive

Definition

ChEBI: Lidocaine is the monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline. It has a role as a local anaesthetic, an anti-arrhythmia drug, an environmental contaminant, a xenobiotic and a drug allergen. It is a monocarboxylic acid amide, a tertiary amino compound and a member of benzenes. It derives from a glycinamide.

Indications

Experimentally, lidocaine has been found to prevent VF arising during myocardial ischemia or infarction by preventing the fragmentation of organized largewavefronts into heterogeneous wavelets. Although lidocaine is of proven benefit in preventing VF early after clinical myocardial infarction, there is no evidence that it reduces mortality. To the contrary, lidocaine may increase mortality after myocardial infarction by approximately 40% to 60%.There are no controlled studies of lidocaine in secondary prevention of recurrence of VT or VF.
Lidocaine terminates organized monomorphic spontaneous VT or induced sustained VT in only approximately 20% of cases and is less effective than many other antiarrhythmic drugs. In a blinded, randomized study of intravenous lidocaine versus intravenous amiodarone in out-of-hospital VF resistant to defibrillation, lidocaine was associated with half the likelihood of survival to hospital admission compared with amiodarone.

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

Alphacaine (Carlisle); Lidoderm (Teikoku); Xylocaine (AstraZeneca).

Therapeutic Function

Local anesthetic, Antiarrhythmic

General Description

Lidocaine was the first amino amide synthesized in 1948and has become the most widely used local anesthetic. Thetertiary amine has a pKa of 7.8 and it is formulated as thehydrochloride salt with a pH between 5.0 and 5.5. When lidocaineis formulated premixed with epinephrine the pH ofthe solution is adjusted to between 2.0 and 2.5 to prevent the hydrolysis of the epinephrine. Lidocaine is also availablewith or without preservatives. Some formulations of lidocainecontain a methylparaben preservative that maycause allergic reactions in PABA-sensitive individuals. Thelow pKa and medium water solubility provide intermediateduration of topical anesthesia of mucous membranes.Lidocaine can also be used for infiltration, peripheral nerveand plexus blockade, and epidural anesthesia.

Biological Activity

Anasthetic and class Ib antiarrhythmic agent.? Blocks voltage-gated sodium channels in the inactivated state.

Contact allergens

Lidocaine 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.

Biochem/physiol Actions

Na+ channel blocker; class IB antiarrhythmic that is rapidly absorbed after parenteral administration.

Pharmacology

Lidocaine is the most widely used local anaesthetic. It has a rapid onset and short duration of action. Lidocaine is rapidly and extensively metabolised in the liver and is safe at recommended doses. Efficacy is enhanced markedly and duration of action prolonged by addition of adrenaline. Lidocaine is less toxic than bupivacaine; a testament to this relative safety is that lidocaine is used intravenously as a class 1b antiarrhythmic and as an i.v. infusion to treat refractory chronic pain. Lidocaine solutions for injection are available in concentrations of 1% and 2%, with or without adrenaline. It is also available as a spray (4% or 10%), cream (2% or 4%), ointment or medicated plaster (both 5%) for topical application.

Pharmacokinetics

Lidocaine is administered intravenously because extensive first-pass transformation by the liver prevents clinically effective plasma concentrations orally. The drug is dealkylated and eliminated almost entirely by the liver; therefore, dosage adjustments are necessary in the presence of hepatic disease or dysfunction. Lidocaine clearance exhibits the time dependency common to high-clearance agents. With a continuous infusion lasting more than 24 hours, there is a decrease in total lidocaine clearance and an increase in elimination half-life compared with a single dose. Lidocaine free plasma levels can vary in certain patients owing to binding with albumin and the acutephase reactant a1-acid glycoprotein. Levels of a1-acid glycoprotein are increased in patients after surgery or acute myocardial infarction, whereas levels of both a1-acid glycoprotein and serum albumin are decreased in chronic hepatic disease or heart failure and in those who are malnourished. This is an essential consideration because it is the unbound fraction that is pharmacologically active.

Clinical Use

The metabolism of lidocaine is typical of the amino amideanesthetics . The liver is responsiblefor most of the metabolism of lidocaine and any decreasein liver function will decrease metabolism. Lidocaineis primarily metabolized by de-ethylation of the tertiary nitrogento form monoethylglycinexylidide (MEGX). At lowlidocaine concentrations, CYP1A2 is the enzyme responsiblefor most MEGX formation. At high lidocaine concentrations,both CYP1A2 and CYP3A4 are responsible for the formationof MEGX.

Side effects

Central nervous system side effects such as drowsiness, slurred speech, paresthesias, agitation, and confusion predominate. These symptoms may progress to convulsions and respiratory arrest with higher plasma concentrations. A rare adverse effect is malignant hyperthermia.
Cimetidine significantly reduces the systemic clearance of lidocaine as well as the volume of distribution at steady state and the degree of plasma protein binding. Beta blockers also reduce lidocaine clearance owing to a decrease in hepatic blood flow. For the same reason, clearance is reduced in congestive heart failure or low-output states.
Amiodarone may also influence the pharmacokinetics of lidocaine. In patients receiving amiodarone, single doses of intravenous lidocaine do not influence the pharmacokinetics of either agent. When amiodarone treatment is started in patients who are already receiving lidocaine infusion, there is a decrease in lidocaine clearance, which can result in toxic lidocaine levels.

Safety Profile

Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human systemic effects: blood pressure lowering, changes in heart rate, coma, convulsions, dlstorted perceptions, dyspnea, excitement, hallucinations, muscle contraction or spasticity, pulse rate, respiratory depression, toxic psychosis. An experimental teratogen. Other experimental reproductive effects. A local anesthetic. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

Lidocaine, 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide (2.2.2), is synthesized from 2,6-dimethylaniline upon reaction with chloroacetic acid chloride, which gives |á-chloro-2,6-dimethylacetanilide (2.1.1), and its subsequent reaction with diethylamine [11].
Synthesis of Lidocaine, 137-58-6
Synthesis of Lidocaine

Veterinary Drugs and Treatments

Besides its use as a local and topical anesthetic agent, lidocaine is used to treat ventricular arrhythmias, principally ventricular tachycardia and ventricular premature complexes in all species. Cats may be more sensitive to the drug and some clinicians feel that it should not be used in this species as an antiarrhythmic, but this remains controversial. In horses, lidocaine may be useful to prevent postoperative ileus and reperfusion injury.

Electrophysiologic Effects

Experimentally, lidocaine has been found to prevent VF arising during myocardial ischemia or infarction by preventing the fragmentation of organized largewavefronts into heterogeneous wavelets. Although lidocaine is of proven benefit in preventing VF early after clinical myocardial infarction, there is no evidence that it reduces mortality. To the contrary, lidocaine may increase mortality after myocardial infarction by approximately 40% to 60%.There are no controlled studies of lidocaine in secondary prevention of recurrence of VT or VF.
Lidocaine terminates organized monomorphic spontaneous VT or induced sustained VT in only approximately 20% of cases and is less effective than many other antiarrhythmic drugs. In a blinded, randomized study of intravenous lidocaine versus intravenous amiodarone in out-of-hospital VF resistant to defibrillation, lidocaine was associated with half the likelihood of survival to hospital admission compared with amiodarone.

Drug interactions

The concurrent administration of lidocaine with cimetidine but not ranitidine may cause an increase (15%) in the plasma concentration of lidocaine. This effect is a manifestation of cimetidine reducing the clearance and volume of distribution of lidocaine. The myocardial depressant effect of lidocaine is enhanced by phenytoin administration.

Metabolism

Lidocaine is extensively metabolized in the liver by N-dealkylation and aromatic hydroxylations catalyzed by CYP1A2 isozymes. Lidocaine also possesses a weak inhibitory activity toward the CYP1A2 isozymes and, therefore, may interfere with metabolism of other medications.

storage

Store at RT

Toxicity evaluation

The potency of lidocaine depends on various factors including age of the subject, weight, physique including obesity, vascularity of the site, and indication for use, as this would determine the absorption and excretion rate. Physiologically, lidocaine blocks neuronal transmission by interfering with the flow of sodium across excitable membranes. A single lidocaine molecule binds to a single voltage-gated sodium channel impeding the movement of sodium ions across neuronal membranes. Consequently repolarization is prevented and further depolarization is not possible. Toxicity is dose related and results from excessive quantities of lidocaine.

Precautions

Contraindications include hypersensitivity to local anesthetics of the amide type (a very rare occurrence), severe hepatic dysfunction, a history of grand mal seizures due to lidocaine, and age 70 or older. Lidocaine is contraindicated in the presence of second- or thirddegree heart block, since it may increase the degree of block and can abolish the idioventricular pacemaker responsible for maintaining the cardiac rhythm.

29183-14-0
109-89-7
137-58-6
Synthesis of Lidocaine from N-(2,6-DIMETHYLPHENYL)-2-HYDROXYACETAMIDE and Diethylamine
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View Lastest Price from Lidocaine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Lidocaine base  pictures 2024-03-19 Lidocaine base
137-58-6
US $0.00-0.00 / kg 1kg 99% 500 Wuhan Haorong Biotechnology Co.,Ltd
 Tetramisole hydrochloride pictures 2024-03-19 Tetramisole hydrochloride
137-58-6
US $15.00-10.00 / kg 1kg 99.5 10 ton per month Nanjing Deda New Material Technology Co., Ltd
Lidocaine pictures 2024-03-19 Lidocaine
137-58-6
US $30.00-10.00 / kg 1kg 99% 300tons Hebei Dangtong Import and export Co LTD
  • Lidocaine base  pictures
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    137-58-6
  • US $0.00-0.00 / kg
  • 99%
  • Wuhan Haorong Biotechnology Co.,Ltd
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  • Lidocaine
    137-58-6
  • US $30.00-10.00 / kg
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  • Hebei Dangtong Import and export Co LTD
2-(Diethylamino)-2',6'-acetoxylidide 2-(diethylamino)-2’,6’-acetoxylidide 2-(diethylamino)-n-(2,6-dimethylphenyl)-acetamid 2',6'-Acetoxylidide, 2-(diethylamino)- 6’-acetoxylidide,2-(diethylamino)-2 Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)- N-Di-ethylaminoacetyl-2,6-dimethylaniline Lidocaine solution omega-Diethylamino-2,6-dimethylacetanilide Remicaine Rucaina Solarcaine aloe extra burn relief cream Solcain Xilina Xllina Xycaine Xylestesin Xylocitin Xyloneural (free base) Xylotox BULK DRUGS. LIDOCAINE USP Acetamide,2-(diethylamino)-N-(2,6-dimethylphenyl)- a-Diethylamino-2,6-acetoxylidide alfa-Dietilamino-2,6-dimetilacetanilide alpha-(Diethylamino)-2,6-acetoxylidide alpha-diethylamino-2,6-acetoxylidide alpha-Diethylamino-2,6-dimethylacetanilide alpha-Diethylaminoaceto-2,6-xylidide Anbesol Broncaine Cappicaine Cito optadren component of Cracked heel relief cream component of Emla cream component of Neosporin plus Cuivasil Dalcaine Diethylaminoacet-2,6-xylidide Diethylaminoaceto-2,6-xylidide Duncaine Esracaine Gravocain Isicaina Isicaine L-Caine Leostesin Lida-Mantle Lidocaine M Lidothesin LIDOCAINE-D6 LIDOCAINE BASE USP 2-Diethylamino-2,6-acetoxylidid 2-Diethylamino-N-(2,6-dimethylphenyl)acetamide, Lignocaine, Xylocaine 2-diethylaminoacet-2,6-xylidide lidocaine(xylocaine) Lidocaine (base and/or unspecified salts) Lidocaine USP Base LidocaineMonohydrateUsp