| Identification | More | [Name]
Cinchocaine | [CAS]
85-79-0 | [Synonyms]
2-BUTOXY-N-[2-(DIETHYLAMINO)-ETHYL]-4-QUINOLINE CARBOXAMIDE
2-BUTOXY-N-[2-(DIETHYLAMINO)ETHYL]CINCHONAMIDE
2-butoxy-n-(2-diethylaminoethyl)quinoline-4-carboxamide
A-BUTOXYCINCHONINIC ACID DIETHYLETHYLENEDIAMIDE
CINCHOCAINE
DIBUCAINE
DIBUCAINE BASE
2-butoxy-n-(2-(diethylamino)ethyl)-4-quinolinecarboxamid
2-butoxy-n-(2-(diethylamino)ethyl)-cinchoninamid
2-butoxy-n-(2-(diethylamino)ethyl)cinchoninamide
2-butoxy-n-(2-(diethylamino)ethyl-4-quinolinecarboxamid
2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamide
2-Butoxy-N-[2-(diethylamino)ethyl]cinchoninamide
2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamide
2-butoxyquinoline-4-carboxylicaciddiethylaminoethylamide
2-n-butoxy-n-(2-diethylaminoethyl)cinchoninamide
4-Quinolinecarboxamide, 2-butoxy-N-[2-(diethylamino)ethyl]-
alpha-butyloxycinchonicacid-gamma-diethylethylenediamine
alpha-Butyloxycinchoninic acid diethylethylenediamide
alpha-butyloxycinchoninicaciddiethylethylenediamide | [EINECS(EC#)]
201-632-1 | [Molecular Formula]
C20H29N3O2 | [MDL Number]
MFCD00047595 | [Molecular Weight]
343.46 | [MOL File]
85-79-0.mol |
| Questions And Answer | Back Directory | [Preparation]
1. Synthesis of 2-chloro-N-[2-(diethylamino)ethyl]-4-quinoline carboxamide At room temperature, 200 g of 2-hydroxy-4-quinoline carboxylic acid and 1500 ml of toluene were added dropwise to a 3000 ml three-necked flask with stirring. The mixture was heated to 75 °C and reacted for 2 hours. The temperature was lowered to 25 °C and concentrated under reduced pressure. Then, 500 ml of toluene was added and the mixture was concentrated to dryness under reduced pressure. The solution was diluted directly with 2000 ml of toluene and added to a 5000 ml three-necked flask. 100 g of N,N-diethyldiethylamine was added. The mixture was heated to 70 °C and stirred until the reaction was complete. The temperature was lowered to room temperature, water was added and stirred for 30 minutes. The mixture was separated into liquid and liquid layers. The organic layer was washed twice with water and once with saturated brine. The solution was dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to dryness to obtain 274 g of 2-chloro-N-[2-(diethylamino)ethyl]-4-quinoline carboxamide, i.e., octocamide, with a yield of 85%. 2. Synthesis of Cincocaine 200g of cincoamide, 550ml of n-butanol, and 300g of sodium n-butoxide were added to a 3000ml reaction flask. The mixture was gradually heated to reflux for 3 hours, then cooled to room temperature. 1000ml of purified water was added, and the mixture was stirred for 30 minutes. After standing for 30 minutes to separate the layers, the aqueous layer was discarded. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. Then, 500ml of toluene was added, and the mixture was heated to 60℃ and stirred for 30 minutes. After standing, the layers separated. The upper toluene layer was cooled to crystallize, yielding 146g of purified Cinchocaine, with a yield of 65% and a purity of 99.7%. |
| Chemical Properties | Back Directory | [Melting point ]
64° | [Boiling point ]
478.73°C (rough estimate) | [density ]
1.1145 (rough estimate) | [refractive index ]
1.6300 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO:45.0(Max Conc. mg/mL);131.02(Max Conc. mM) | [form ]
Solid:particulate/powder | [pka]
pKa -5.3(aq. H2SO4) (Uncertain) | [color ]
White to yellow | [Water Solubility ]
68.01mg/L(temperature not stated) | [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) | [Contact allergens]
Dibucaine hydrochloride is an amide group local anesthetic
that can induce allergic contact dermatitis. | [InChIKey]
PUFQVTATUTYEAL-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC=CC=2)C(C(NCCN(CC)CC)=O)=CC=1OCCCC | [LogP]
4.4 at 25℃ and pH7 | [CAS DataBase Reference]
85-79-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Dibucaine(85-79-0) |
| Hazard Information | Back Directory | [Uses]
Local anesthesic;Na+ channel blocker | [Definition]
ChEBI: A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally o
ly used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions. | [Originator]
Cincain,Ophtha | [Manufacturing Process]
A benzene solution of 2.2 parts of α-chloro-γ-quinoline-carboxylic acid chloride
is gradually mixed, while cooling, with 2.3 parts of unsymmetrical
diethylethylenediamine. When the reaction is at an end the solution is washed
with water and the new base extracted by means of hydrochloric acid. The
base is precipitated by means of sodium carbonate and extracted with
benzene. The solvent is distilled and the base recrystallized from petroleum
ether. The α-chloro-γ-quinoline-carboxylic acid diethyl-amino-ethylene amide
forms colorless lamina crystals of melting point 74°C. With acids the base
forms neutral salts soluble in water.
A solution of 2.5 parts of sodium in n-butylalcohol is boiled with 30 parts of α-
chloro-γ-quinoline-carboxylic acid diethyl-amino-ethylene-amide in a reflux
apparatus, and when the reaction is over the excess of butylalcohol is
distilled. The remaining base is taken up with ether; the solution is washed
with water and dried. The solvent is then distilled. The α-n-butoxy-γ-quinolinecarboxylic acid diethyl-amino-ethylene-amide forms as colorless crystals, after
recrystallization from petroleum ether melting point of it 64°C.
In practice it is usually used as hydrochloride. | [Brand name]
Nupercaine (Novartis). | [Therapeutic Function]
Local anesthetic | [General Description]
Articaine has a secondary nitrogen with a pKa of 7.8. It containsan aromatic thiophene ring bioisostere of the phenylring found in most other amide anesthetics. The log P of abenzene ring is 2.13 and the thiophene ring log P is 1.81,thus the thiophene ring is more hydrophilic than a phenylring. Although the thiophene ring has less lipid solubilitythan a phenyl ring, articaine is a lipid-soluble compound dueto the propylamine, the branched methyl and the substitutionson the thiophene ring. The onset of action of articaineis similar to lidocaine’s onset of action. | [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. | [storage]
Store at -20°C | [References]
[1] Patent: CN108003097, 2018, A. Location in patent: Paragraph 0020-0022; 0023-0025; 0026-0028 |
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