Lidocaine

Base Information

• Chemical Name: Lidocaine
• CAS No.: 137-58-6
• Deprecated CAS: 8059-42-5,8059-66-3,91484-71-8,8059-66-3,91484-71-8
• Molecular Formula: C14H22N2O
• Molecular Weight: 234.341
• Hs Code.: DERIVATION
• European Community (EC) Number: 205-302-8,684-578-5
• NSC Number: 40030
• UNII: 98PI200987
• DSSTox Substance ID: DTXSID1045166
• Nikkaji Number: J5.631F
• Wikipedia: Lidocaine
• Wikidata: Q216935
• NCI Thesaurus Code: C614
• RXCUI: 6387
• Pharos Ligand ID: 8NFQNG6H36UD
• Metabolomics Workbench ID: 42673
• ChEMBL ID: CHEMBL79
• Mol file: 137-58-6.mol

Synonyms:2-(Diethylamino)-N-(2,6-Dimethylphenyl)Acetamide;2-2EtN-2MePhAcN;Dalcaine;Lidocaine;Lidocaine Carbonate;Lidocaine Carbonate (2:1);Lidocaine Hydrocarbonate;Lidocaine Hydrochloride;Lidocaine Monoacetate;Lidocaine Monohydrochloride;Lidocaine Monohydrochloride, Monohydrate;Lidocaine Sulfate (1:1);Lignocaine;Octocaine;Xylesthesin;Xylocaine;Xylocitin;Xyloneural

Chemical Property of Lidocaine

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 4.28E-05mmHg at 25°C
• Melting Point: 66-69 °C
• Refractive Index: 1.5110 (estimate)
• Boiling Point: 350.8 °C at 760 mmHg
• PKA: pKa 7.88(H2O)(Approximate)
• Flash Point: 166 °C
• PSA: 32.34000
• Density: 1.026 g/cm³
• LogP: 2.65670
• Storage Temp.: Store at RT
• Solubility.: ethanol: 4 mg/mL
• Water Solubility.: practically insoluble
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 234.173213330
• Heavy Atom Count: 17
• Complexity: 228

Purity/Quality:

99% ^*data from raw suppliers

Lidocaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 22-26-36-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CC(=O)NC1=C(C=CC=C1C)C
• Recent ClinicalTrials: IV Lidocaine Analgesia in Pediatric Scoliosis Surgery
• Recent EU Clinical Trials: Effect of 0.5% local lidocaine injection on the prevention of acute
• Recent NIPH Clinical Trials: Trial of trigger point injections for myofascial pain in patients with cancer
• 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.
• 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. 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. 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 Antiarrhythmic Agents, Anesthetics；Anticonvulsant；antihypertensive
• 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).
• 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.
• Therapeutic Function: Local anesthetic, Antiarrhythmic
• 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.
• 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.

Technology Process of Lidocaine

There total 17 articles about Lidocaine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

diethylamine (109-89-7) + 2-chloro-N-(2,6-dimethylphenyl)acetamide (1131-01-7) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 99 ℃; under 5171.62 Torr; Temperature; Flow reactor;

DOI:10.1002/anie.201809080

Reference yield: 95.2%

diethylamine (109-89-7) + chloroacetyl chloride (79-04-9) + 2,6-dimethylaniline (87-62-7) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Guidance literature:

chloroacetyl chloride; 2,6-dimethylaniline; In toluene; at 80 - 90 ℃; for 3h; Large scale;

With sodium carbonate; potassium iodide; In water; toluene; for 0.5h; Large scale;

diethylamine; In water; toluene; Solvent; Temperature; Reagent/catalyst; Large scale;

Reference yield: 95.0%

(2-diethylaminoethyl)amide (7409-48-5) + 2,6-dimethylaniline (87-62-7) → 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6)

Guidance literature:

With dipotassium peroxodisulfate; In water; at 100 ℃; for 0.166667h; Microwave irradiation; Green chemistry;

DOI:10.1016/j.tetlet.2015.06.052

upstream raw materials:

diethylamine

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

denatonium benzoate

2,6-dimethylaniline

Downstream raw materials:

QX-314

denatonium chloride

2-diethylamino-N-(2,6-dimethyl-3-nitro-phenyl)-acetamide

N-(3-bromo-2,6-dimethyl-phenyl)-2-diethylamine-acetamide

Refernces

• 1、 McKenzie. "Disproportionation of lidocaine sulfate dihydrate in certain organic solvents.". . p. 1297 - 1298. Retrieved 1969.
• 2、 -. "Carboxyesterase polypeptides for amide coupling". Page/Page column 65-66; 73-84. . Retrieved 2021/05/28.
• 3、 -. "Method for preparing lidocaine intermediate alpha-chloroacetyl-2, 6-dimethylaniline and lidocaine without adding extra alkali". Paragraph 0065; 0070-0072; 0074; 0079-0080; 0082; 0087-0088. . Retrieved 2020/06/30.