2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide;hydron;chloride
Basic information
- CAS
73-78-9- Standard SMILES
CCN(CC)CC(=O)Nc1c(C)cccc1C.[Cl-].[H+]- InChIKey
IYBQHJMYDGVZRY-UHFFFAOYSA-N- Molecular formula
- C14H23ClN2O
- Average molar mass
- 270.8 g/mol
- Monoisotopic mass
- 270.1498911
Overview
See also: Lidocaine Hydrochloride (preferred); Lidocaine (has active moiety); Allantoin; Lidocaine Hydrochloride (component of) ... View More ...
Names & identifiers
- Preferred name
- 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide;hydron;chloride
- IUPAC
- 2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide;hydron;chloride
- English name
- Lidocaine hydrochloride
- Molecular formula
- C14H23ClN2O
- Molecular weight
- 270.8
Names & synonyms
SCHEMBL29129AKOS026750038LIDOCAINE HCLLIGNOCAINE HYDROCHLORIDELidocainLidocaine HCILidocaine hydrochloride CP2000,BP98rucainahydrochlorideduncainehydrochloridegravocainhydrochlorideleostesinhydrochloridexylocitinhydrochloride
Database identifiers
- CAS
73-78-9- PubChem CID
- 657223
Properties
Computed structural properties
- Topological polar surface area
- 32.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 228
Physicochemical properties
- Melting point
- 80 · 80-82°C
- storage temp.
- 2 · Inert atmosphere,2-8°C
- form
- Solid
- color
- White to off-white
- Water Solubility
- 36 mg/mL · Water : ≥ 36 mg/mL (132.94 mM)
- InChI
- InChI=1S/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
- InChIKey
- IYBQHJMYDGVZRY-UHFFFAOYSA-N
- SMILES
- C(NC1=C(C)C=CC=C1C)(=O)CN(CC)CC.[H]Cl
- LogP
- 2.359 · 2.359 (est)
- CAS DataBase Reference
- 73 · 73-78-9(CAS DataBase Reference)
- FDA 21 CFR
- 310.545 · 310.545
- EWG's Food Scores
- 1 · 1-3
- FDA UNII
- 2 CNF7XFP · EC2CNF7XFP
- NCI Drug Dictionary
- lidocaine hydrochloride
- EPA Substance Registry System
- 2 · Acetamide, 2-(diethylamino)-N-(2,6-dimethylphenyl)-, monohydrochloride (73-78-9)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- tsca
- TSCA listed
- ridadr
- 3249
- Toxicity
- LD50 oral in mouse: 220mg/kg
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_class
- 6.1(b)
- packing_group
- III
- Hazard statements
- H302
- Precautionary statements
- P264-P270-P301+P312-P330-P501
Chemistry & industry
Applications
UsesApply to affected site 5 to 10 minutes before procedure. Duration of anesthesia is relatively short (
UsesLocal anesthesic;Na+ channel blocker
UsesAnesthetic (local); antiarrhythmic (class IB). Long-acting, membrane stabilizing agent against ventricular arrhythmia. Originally developed as a local anesthetic.
General DescriptionLidocaine 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.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: Lidocaine hydrochloride is the anhydrous form of the hydrochloride salt of lidocaine. It functions as both a local anesthetic and cardiac depressant, and is commonly used as an antiarrhythmic agent. Its potency is higher and its effects last longer than those of procaine, but its duration of action is shorter than that of bupivacaine or prilocaine.
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