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137-58-6

137-58-6 Structure

137-58-6 Structure
IdentificationMore
[Name]

Xylocaine
[CAS]

137-58-6
[Synonyms]

4,4'-DIMETHOXY DIPHENYL SULFOXIDE
LIDOCAINE-D6
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)-
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
Anestacon
Broncaine
Cappicaine
Cito optadren
[EINECS(EC#)]

205-302-8
[Molecular Formula]

C14H14O3S
[MDL Number]

MFCD08443609
[Molecular Weight]

262.32
[MOL File]

137-58-6.mol
Chemical PropertiesBack Directory
[Appearance]

solid
[Melting point ]

66-69°C
[mp ]

66-69°C
[Boiling point ]

bp4 180-182°; bp2 159-160°
[density ]

0.9944 (rough estimate)
[refractive index ]

1.5110 (estimate)
[Fp ]

9℃
[storage temp. ]

Store at RT
[solubility ]

ethanol: 4 mg/mL
[pka]

pKa 7.88(H2O)(Approximate)
[form ]

powder
[color ]

White to slightly yellow
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[Water Solubility ]

practically insoluble
[Merck ]

5482
[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.
[InChIKey]

NNJVILVZKWQKPM-UHFFFAOYSA-N
[CAS DataBase Reference]

137-58-6(CAS DataBase Reference)
[NIST Chemistry Reference]

Lidocaine(137-58-6)
[EPA Substance Registry System]

137-58-6(EPA Substance)
Questions And AnswerBack Directory
[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.
[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]

1, This product is a local anesthetics of amide derivatives,and widely used in surface anesthesia, anesthesia, conduction anesthesia and epidural anesthesia. The LD50 of oral lidocaine hydrochloride to mice was 290 mg/kg.
2, Used as a local anesthetic.
Hazard InformationBack Directory
[Chemical Properties]

solid
[Definition]

ChEBI: The monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.
[Biological Activity]

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

Xylocaine,Astra,US,1949
[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.
[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.
[Chemical 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 α-chloro-2,6-dimethylacetanilide (2.1.1), and its subsequent reaction with diethylamine [11].

[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.
[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.
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R22:Harmful if swallowed.
[Safety Statements ]

S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[RIDADR ]

3249
[WGK Germany ]

3
[RTECS ]

AN7525000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29242990
[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.
[Hazardous Substances Data]

137-58-6(Hazardous Substances Data)
[Toxicity]

LD50 oral in rat: 317mg/kg
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Diethylamine-->Chloroacetyl chloride-->N-Methylaniline-->Lidocaine hydrochloride-->[(2,6-DIMETHYLPHENYL)AMINOCARBONYLMETHYL]CHLORIDE-->2,6-Dimethylaniline-->2,6-DI-O-METHYL-BETA-CYCLODEXTRIN
【Preparation Products】

N-ETHYLLIDOCAINE BROMIDE
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Xylocaine(137-58-6).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Xylocaine(137-58-6) IR2
Xylocaine(137-58-6) IR1
Xylocaine(137-58-6) MS
Xylocaine(137-58-6) 13C NMR
Xylocaine(137-58-6) 1H NMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2-(Diethylamino)-N-(2,6-dimethylphenyl)-acetamide, 97.5%(137-58-6)
[Sigma Aldrich]

137-58-6(sigmaaldrich)
[TCI AMERICA]

Lidocaine,>99.0%(LC)(T)(137-58-6)
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