2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide

• ChemBase ID: 409
• Molecular Formular: C20H29N3O2
• Molecular Mass: 343.46316
• Monoisotopic Mass: 343.22597718
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 85-79-0
• EC Number: 201-632-1
• MDL Number: MFCD00047595
• PubChem SID: 46506734; 24893238; 160963872
• PubChem CID: 3025
• CHEBI ID: 247956
• ATC CODE: C05AD04; N01BB06; S02DA04; S01HA06; D04AB02
• CHEMBL: 1086
• Chemspider ID: 2917
• DrugBank ID: DB00527
• KEGG ID: D00733
• Unique Ingredient Identifier: L6JW2TJG99
• Wikipedia Title: Dibucaine

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.57441
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.47672126
• LogD (pH = 7.4): 2.0500696
• Log P: 3.6981626
• Molar Refractivity: 102.121 cm^3
• Polarizability: 40.42192 Å^3
• Polar Surface Area: 54.46 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.79
• LOG S: -3.95
• Solubility (Water): 3.89e-02 g/l

PROPERTIES

Physical Property

• Solubility: 42 mg/L
• Hydrophobicity(logP): 4.2

Safety Information

• RTECS: GD3150000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Admin Routes: topical, intravenous (equine euthanasia)

Product Information

• Grade: analytical standard

DETAILS

MP Biomedicals - 05201127

MP Biomedicals Rare Chemical collection

DrugBank - DB00527

• 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

Frequently Asked Questions
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Biochem/physiol Actions
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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

• 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