Dibucaine

Base Information

• Chemical Name: Dibucaine
• CAS No.: 85-79-0
• Molecular Formula: C20H29N3O2
• Molecular Weight: 343.469
• Hs Code.: 2933499090
• European Community (EC) Number: 201-632-1
• NSC Number: 159055
• UNII: L6JW2TJG99
• DSSTox Substance ID: DTXSID3045271
• Nikkaji Number: J3.887C
• Wikipedia: Cinchocaine
• Wikidata: Q417603
• NCI Thesaurus Code: C28984
• RXCUI: 3339
• Pharos Ligand ID: C3CTPTKKG326
• Metabolomics Workbench ID: 42866
• ChEMBL ID: CHEMBL1086
• Mol file: 85-79-0.mol

Synonyms:Cincain;Cinchocaine;Dibucaine;Nupercainal;Nupercaine;Sovcaine

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Chemical Property of Dibucaine

Chemical Property:

• Vapor Pressure: 5.46E-10mmHg at 25°C
• Melting Point: -51 °C
• Refractive Index: 1.557
• Boiling Point: 496.3 °C at 760 mmHg
• PKA: pKa -5.3(aq. H2SO4) (Uncertain)
• Flash Point: 254 °C
• PSA: 54.46000
• Density: 1.071 g/cm³
• LogP: 3.87620
• Water Solubility.: 68.01mg/L(temperature not stated)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 343.22597718
• Heavy Atom Count: 25
• Complexity: 387

Purity/Quality:

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
• Uses: Cinchocaine is a local anesthesic,used for Na+ channel blocker.
• Therapeutic Function: Local anesthetic
• Clinical Use: Articaine is availablein a 4% solution with epinephrine for use in infiltrationand nerve block anesthesia.Articaine is metabolized rapidly via plasma and tissuecarboxyesterase to its primary metabolite, the inactive,water-soluble carboxylic acid. Approximately 40% to 70%of articaine administered epidurally is metabolized to thecarboxylic acid, articainic acid. Approximately 4% to 15%of the articainic acid undergoes glucuronide conjugationand only 3% of the dose is recovered unchanged in theurine. The rapid plasma metabolism and reported inactivityof the carboxylic acid metabolite make articaine a potentiallysafer anesthetic agent when multiple or large dosesare necessary.

Technology Process of Dibucaine

There total 7 articles about Dibucaine 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: 96.4%

2-chloro-quinoline-4-carboxylic acid-(2-diethylamino-ethylamide) (87864-14-0) + butan-1-ol (71-36-3) → Dibucaine (85-79-0)

Guidance literature:

With sodium hydroxide; In hexane; Solvent; Reflux;

Reference yield:

2-chloroquinoline-4-carbonyl chloride (2388-32-1) → Dibucaine (85-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1: butan-1-ol

With butan-1-ol;

Reference yield:

2-chloroquinoline-4-carboxylic acid (5467-57-2) → Dibucaine (85-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N,N-dimethyl-formamide; thionyl chloride / dichloromethane / 4 h / 55 °C

2.1: triethylamine / dichloromethane / 0.25 h / Cooling with ice

2.2: 20 °C / Cooling with ice

3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere; Cooling with ice

3.2: 72 h / 80 °C / Inert atmosphere

With thionyl chloride; sodium hydride; triethylamine; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

2-butoxy-quinoline-4-carboxylic acid amide

2-(n-butyloxy)-4-(n-butyloxycarbonyl)-quinoline

N,N-diethylethylenediamine

sodium butanolate

Refernces

• 1、 -. "Quinoline formamide compound and preparation method thereof and application of anti-enterovirus type 71". Paragraph 0036-0043. . Retrieved 2020/01/03.