2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide;hydron;chloride

Base Information

• Chemical Name: 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide;hydron;chloride
• CAS No.: 73-78-9
• Molecular Formula: C14H22N2O.HCl
• Molecular Weight: 270.802
• Hs Code.: 2924299090
• Mol file: 73-78-9.mol

Synonyms:Linocaine hydrochloride;SCHEMBL29129;AKOS026750038

Chemical Property of 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide;hydron;chloride

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 4.28E-05mmHg at 25°C
• Melting Point: 80-82 °C
• Boiling Point: 350.8 °C at 760 mmHg
• Flash Point: 166 °C
• PSA: 32.34000
• LogP: 3.45870
• Storage Temp.: Refrigerator
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 270.1498911
• Heavy Atom Count: 18
• Complexity: 228

Purity/Quality:

99%, ^*data from raw suppliers

Lidocaine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: [H+].CCN(CC)CC(=O)NC1=C(C=CC=C1C)C.[Cl-]
• 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.
• Uses: Apply to affected site 5 to 10 minutes before procedure. Duration of anesthesia is relatively short (<1 hour).
• 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.
• 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.

Technology Process of 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide;hydron;chloride

There total 4 articles about 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide;hydron;chloride 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: 100.0%

2-diethylamino-N-(2,6-dimethylphenyl)-acetamide (137-58-6) → lidocaine hydrochloride (73-78-9)

Guidance literature:

With hydrogenchloride; In diethyl ether;

DOI:10.1016/j.saa.2015.07.060

Reference yield:

diethylamine (109-89-7) + chloroacetyl chloride (79-04-9) + 2,6-dimethylaniline (87-62-7) → lidocaine hydrochloride (73-78-9)

Guidance literature:

chloroacetyl chloride; 2,6-dimethylaniline; In 1-methyl-pyrrolidin-2-one; methanol; water; at 120 ℃; for 0.306667h; Flow reactor;

diethylamine; With potassium hydroxide; In methanol; water; at 130 ℃; for 0.295h; under 12751.3 Torr; Flow reactor;

With hydrogenchloride; In methanol; diethyl ether; water;

DOI:10.1126/science.aaf1337

Reference yield:

2.6-dimethylphenol (576-26-1,25134-01-4) → lidocaine hydrochloride (73-78-9)

Guidance literature:

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

With hydrogenchloride; 2,6-dimethylcyclohexanone; ammonium hydroxide; 5%-palladium/activated carbon; sodium methylate; pyrographite; In water; 1,2-dichloro-ethane;

upstream raw materials:

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

diethylamine

chloroacetyl chloride

2,6-dimethylaniline

Downstream raw materials:

lidocaine N-oxide

lidocainium ibuprofenate

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

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

Refernces

• 1、 -. "Preparation method of lidocaine hydrochloride". Paragraph 0031; 0037-0038. . Retrieved 2020/01/25.
• 2、 Adamo, Andrea,Beingessner, Rachel L.,Behnam, Mohsen,Chen, Jie,Jamison, Timothy F.,Jensen, Klavs F.,Monbaliu, Jean-Christophe M.,Myerson, Allan S.,Revalor, Eve M.,Snead, David R.,Stelzer, Torsten,Weeranoppanant, Nopphon,Wong, Shin Yee,Zhang, Ping. "On-demand continuous-flow production of pharmaceuticals in a compact, reconfigurable system". . p. 61 - 67. Retrieved 2016/04/26.