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137-58-6 molecular structure
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2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide

ChemBase ID: 166
Molecular Formular: C14H22N2O
Molecular Mass: 234.33728
Monoisotopic Mass: 234.17321333
SMILES and InChIs

SMILES:
O=C(Nc1c(cccc1C)C)CN(CC)CC
Canonical SMILES:
CCN(CC(=O)Nc1c(C)cccc1C)CC
InChI:
InChI=1S/C14H22N2O/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)
InChIKey:
NNJVILVZKWQKPM-UHFFFAOYSA-N

Cite this record

CBID:166 http://www.chembase.cn/molecule-166.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide
IUPAC Traditional name
lignocaine
2-(diethylamino)-N-(2,6-dimethylphenyl)acetamide
Brand Name
Dalcaine
Lidoject-1
Lidoject-2
Octocaine
Xylocaine
Xylocaine-MPF
Xylocaine-MPF with Glucose
Octocaine-50
Octocaine-100
Xylocaine Test Dose
Xylocaine 5% Spinal
After Burn Double Strength Gel
After Burn Double Strength Spray
After Burn Gel
After Burn Spray
Alphacaine
Anestacon
Anestacon Jelly
Cappicaine
DermaFlex
Duncaine
Emla
Esracaine
Gravocain
Isicaina
Lanabiotic
Leostesin
Lidoderm
Lignocaine
Maricaine
Norwood Sunburn Spray
Rocephin Kit
Xylocaine Dental Ointment
Xylocaine Endotracheal
Xylocaine Viscous
Xylocard
Zilactin-L
Solarcaine
Solarcaine aloe extra burn relief cream
Solcain
Zingo
Synonyms
Dilocaine
L-Caine
Lidocaine
Alphacaine
Xylocaine
N1-(2,6-Dimethylphenyl)-N2,N2-diethylglycinamide
''N''-(2,6-dimethylphenyl)-''N''2,''N''2-diethylglycinamide
2-(Diethylamino)-2',6'-Acetoxylidide
2-Diethylamino-N-(2,6-dimethylphenyl)acetamide
Broncaine
Xilina
Xycaine
Xyline
lignocaine
Lidocaine(Alphacaine)
Lidocaine
CAS Number
137-58-6
EC Number
205-302-8
MDL Number
MFCD00026733
PubChem SID
24896272
24896480
46505060
160963629
PubChem CID
367
3676
CHEBI ID
6456
ATC CODE
S02DA01
C05AD01
D04AB01
C01BB01
N01BB02
CHEMBL
79
Chemspider ID
3548
DrugBank ID
DB00281
IUPHAR ligand ID
2623
KEGG ID
D00358
Unique Ingredient Identifier
98PI200987
Wikipedia Title
Lidocaine

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.775423  H Acceptors
H Donor LogD (pH = 5.5) 0.6099084 
LogD (pH = 7.4) 2.329713  Log P 2.8429134 
Molar Refractivity 73.9296 cm3 Polarizability 27.641424 Å3
Polar Surface Area 32.34 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.81  LOG S -2.6 
Solubility (Water) 5.93e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
4100 mg/L expand Show data source
Apperance
powder expand Show data source
Melting Point
66-69°C expand Show data source
68°C (154.4°F) expand Show data source
Boiling Point
180°C expand Show data source
Hydrophobicity(logP)
2.1 expand Show data source
Storage Condition
-20°C expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
AN7525000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
R:22 expand Show data source
Safety Statements
22-26-36 expand Show data source
S:36/37/39 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Target
Histamine receptors expand Show data source
Admin Routes
IV, subcutaneous, topical expand Show data source
Bioavailability
35% (oral)
3% (topical)
expand Show data source
Excretion
renal expand Show data source
Half Life
1.5–2 hours expand Show data source
Metabolism
Hepatic, 90% CYP1A2-mediated expand Show data source
Legal Status
Rx Only (U.S.) (excluding 1%) (US) expand Show data source
S4 (Australia) expand Show data source
Pregnancy Category
A (Australia) expand Show data source
B (US) expand Show data source
Gene Information
human ... CYP1A2(1544)rat ... Scnn1a(25122) expand Show data source
Mechanism of Action
Potassium channel (K ATP and K Vol ) blocker expand Show data source
Grade
analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Packaging
vial of 200 mg expand Show data source
Application(s)
Antiarrhythmic agent expand Show data source
Local anaesthetic expand Show data source
Pharmacopeia Traceability
traceable to BP 727 expand Show data source
traceable to PhEur L0595000 expand Show data source
traceable to USP 1366002 expand Show data source
Empirical Formula (Hill Notation)
C14H22N2O expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich Wikipedia Wikipedia
DrugBank - DB00281 external link
Item Information
Drug Groups approved
Description A local anesthetic and cardiac depressant used as an antiarrhythmia agent. Its actions are more intense and its effects more prolonged than those of procaine but its duration of action is shorter than that of bupivacaine or prilocaine. [PubChem]
Indication For production of local or regional anesthesia by infiltration techniques such as percutaneous injection and intravenous regional anesthesia by peripheral nerve block techniques such as brachial plexus and intercostal and by central neural techniques such as lumbar and caudal epidural blocks.
Pharmacology Lidocaine is an anesthetic agent indicated for production of local or regional anesthesia and in the treatment of ventricular tachycardia occurring during cardiac manipulation, such as surgery or catheterization, or which may occur during acute myocardial infarction, digitalis toxicity, or other cardiac diseases. The mode of action of the antiarrhythmic effect of Lidocaine appears to be similar to that of procaine, procainamide and quinidine. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole. The sinoatrial node is, however, unaffected. In contrast to the latter 3 drugs, Lidocaine in therapeutic doses does not produce a significant decrease in arterial pressure or in cardiac contractile force. In larger doses, lidocaine may produce circulatory depression, but the magnitude of the change is less than that found with comparable doses of procainamide.
Toxicity The oral LD 50 of lidocaine HCl in non-fasted female rats is 459 (346-773) mg/kg (as the salt) and 214 (159-324) mg/kg (as the salt) in fasted female rats. Symptoms of overdose include convulsions, hypoxia, acidosis, bradycardia, arrhythmias and cardiac arrest.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic.
Absorption Information derived from diverse formulations, concentrations and usages reveals that lidocaine is completely absorbed following parenteral administration, its rate of absorption depending, for example, upon various factors such as the site of administration and the presence or absence of a vasoconstrictor agent.
Half Life 109 minutes
Protein Binding 60-80%
Elimination Lidocaine and its metabolites are excreted by the kidneys.
Distribution * 0.7 to 2.7 L/kg [healthy volunteers]
Clearance * 0.64 +/- 0.18 L/min
References
Khaliq W, Alam S, Puri N: Topical lidocaine for the treatment of postherpetic neuralgia. Cochrane Database Syst Rev. 2007 Apr 18;(2):CD004846. [Pubmed]
Thomson PD, Melmon KL, Richardson JA, Cohn K, Steinbrunn W, Cudihee R, Rowland M: Lidocaine pharmacokinetics in advanced heart failure, liver disease, and renal failure in humans. Ann Intern Med. 1973 Apr;78(4):499-508. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1357 external link
Research Area: Neurological Disease
Biological Activity:
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 structurally related to tricyclic antidepressants such as imipramine, and distantly related to the atypical antipsychotic quetiapine, used to treat allergies. [2]
Sigma Aldrich - 19543 external link
Biochem/physiol Actions
Na+ channel blocker; class IB antiarrhythmic that is rapidly absorbed after parenteral administration.
Sigma Aldrich - L1026 external link
包装
Supplied in amber screw-cap vials
Biochem/physiol Actions
Na+ channel blocker; class IB antiarrhythmic that is rapidly absorbed after parenteral administration.
Sigma Aldrich - L7757 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Na+ channel blocker; class IB antiarrhythmic that is rapidly absorbed after parenteral administration.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Harms, A.F. et al., J. Med. Chem., 1961, 4, 575, (synth, pharmacol)
  • • Garland, W.A. et al., Biomed. Mass Spectrom., 1974, 1, 124, (ms)
  • • Jones, R.L., J. Pharm. Sci., 1974, 63, 1170, (ir)
  • • Yoo, C.S. et al., Acta Cryst. B, 1975, 31, 1354, (cryst struct)
  • • Singh, S.P. et al., Spectrosc. Lett., 1979, 12, 95, (pmr)
  • • Noneman, J.W. et al., Drug Treat. Card. Arrhythmias, 1983, 193, (rev, pharmacol)
  • • Groeningsson, K. et al., Anal. Profiles Drug Subst., 1985, 14, 207, (rev)
  • • Powell, M.F., Anal. Profiles Drug Subst., 1986, 15, 761, (rev)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 3325, (synonyms)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1010
  • • Comer, A.M. et al., Drugs, 2000, 59, 245-249, (rev)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DHK400; DHK600
  • • http://en.wikipedia.org/wiki/Lidocaine
  • • Khaliq W, Alam S, Puri N: Topical lidocaine for the treatment of postherpetic neuralgia. Cochrane Database Syst Rev. 2007 Apr 18;(2):CD004846. Pubmed
  • • Thomson PD, Melmon KL, Richardson JA, Cohn K, Steinbrunn W, Cudihee R, Rowland M: Lidocaine pharmacokinetics in advanced heart failure, liver disease, and renal failure in humans. Ann Intern Med. 1973 Apr;78(4):499-508. Pubmed
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