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85-79-0 molecular structure
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2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide

ChemBase ID: 409
Molecular Formular: C20H29N3O2
Molecular Mass: 343.46316
Monoisotopic Mass: 343.22597718
SMILES and InChIs

SMILES:
O(c1nc2c(c(C(=O)NCCN(CC)CC)c1)cccc2)CCCC
Canonical SMILES:
CCCCOc1nc2ccccc2c(c1)C(=O)NCCN(CC)CC
InChI:
InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)
InChIKey:
PUFQVTATUTYEAL-UHFFFAOYSA-N

Cite this record

CBID:409 http://www.chembase.cn/molecule-409.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
IUPAC Traditional name
dibucaine
Brand Name
Cinchocaine
Cinchocaine HCL
Dermacaine
Dibucain
Dibucaine base
Dibucaine hydrochloride
Heavy Solution Nupercaine
Nupercainal
Nupercaine
Sovcaine
cinchocaine hydrochloride
Synonyms
Dibucaine
CINCHOCAINE
Dibucaine
狄布卡因
CAS Number
85-79-0
EC Number
201-632-1
MDL Number
MFCD00047595
PubChem SID
160963872
46506734
24893238
PubChem CID
3025
CHEBI ID
247956
ATC CODE
S01HA06
D04AB02
C05AD04
S02DA04
N01BB06
CHEMBL
1086
Chemspider ID
2917
DrugBank ID
DB00527
KEGG ID
D00733
Unique Ingredient Identifier
L6JW2TJG99
Wikipedia Title
Dibucaine

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.57441  H Acceptors
H Donor LogD (pH = 5.5) 0.47672126 
LogD (pH = 7.4) 2.0500696  Log P 3.6981626 
Molar Refractivity 102.121 cm3 Polarizability 40.42192 Å3
Polar Surface Area 54.46 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five true 
Log P 3.79  LOG S -3.95 
Solubility (Water) 3.89e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
42 mg/L expand Show data source
Hydrophobicity(logP)
4.2 expand Show data source
RTECS
GD3150000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-41 expand Show data source
Safety Statements
26-39 expand Show data source
GHS Pictograms
GHS05 expand Show data source
GHS07 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H302-H318 expand Show data source
GHS Precautionary statements
P280-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Admin Routes
topical, intravenous (equine euthanasia) expand Show data source
Grade
analytical standard expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05201127 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB00527 external link
Item Information
Drug Groups approved
Description A local anesthetic of the amide type now generally used for surface anesthesia. It is one of the most potent and toxic of the long-acting local anesthetics and its parenteral use is restricted to spinal anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1006)
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 Dibucaine is an amide-type local anesthetic, similar to lidocaine.
Toxicity Subcutaneous LD50 in rat is 27 mg/kg. Symptoms of overdose include convulsions, hypoxia, acidosis, bradycardia, arrhythmias and cardiac arrest.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic.
Absorption In general, ionized forms (salts) of local anesthetics are not readily absorbed through intact skin. However, both nonionized (bases) and ionized forms of local anesthetics are readily absorbed through traumatized or abraded skin into the systemic circulation.
References
Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. [Pubmed]
Souto-Padron T, Lima AP, Ribeiro Rde O: Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res. 2006 Sep;99(4):317-20. Epub 2006 Apr 13. [Pubmed]
Nounou MM, El-Khordagui LK, Khalafallah N: Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles. Acta Pol Pharm. 2005 Sep-Oct;62(5):369-79. [Pubmed]
External Links
Wikipedia
Drugs.com
Sigma Aldrich - D0513 external link
Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
强效、长效局部麻醉剂
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D0513.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Abdel-Ghani NT, Youssef AF, Awady MA: Cinchocaine hydrochloride determination by atomic absorption spectrometry and spectrophotometry. Farmaco. 2005 May;60(5):419-24. Pubmed
  • • Souto-Padron T, Lima AP, Ribeiro Rde O: Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res. 2006 Sep;99(4):317-20. Epub 2006 Apr 13. Pubmed
  • • Nounou MM, El-Khordagui LK, Khalafallah N: Effect of various formulation variables on the encapsulation and stability of dibucaine base in multilamellar vesicles. Acta Pol Pharm. 2005 Sep-Oct;62(5):369-79. Pubmed
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PATENTS

PATENTS

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INTERNET

INTERNET

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