85-79-0 Usage
Description
Cinchocaine, also known as 2-butoxyquinoline-4-carboxylic acid amide, is a potent and toxic monocarboxylic acid amide local anesthetic. It features a secondary nitrogen with a pKa of 7.8 and an aromatic thiophene ring bioisostere of the phenyl ring found in most other amide anesthetics. The thiophene ring is more hydrophilic than a phenyl ring due to its lower log P value, but articaine remains a lipid-soluble compound due to the propylamine, the branched methyl, and the substitutions on the thiophene ring. Its onset of action is similar to that of lidocaine.
Uses
Used in Medical Applications:
Cinchocaine is used as a local anesthetic for blocking Na+ channels, providing temporary pain relief during medical procedures. Its potent and toxic nature has led to its restricted use, primarily in creams, ointments, and suppositories for the 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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 85-79-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 5 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 85-79:
(4*8)+(3*5)+(2*7)+(1*9)=70
70 % 10 = 0
So 85-79-0 is a valid CAS Registry Number.
InChI:InChI=1/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)
85-79-0Relevant articles and documents
Identification of dibucaine derivatives as novel potent enterovirus 2C helicase inhibitors: In vitro, in vivo, and combination therapy study
Chen, Yinuo,Feng, Leilei,Jin, Mengyu,Lan, Ke,Shu, Ting,Tang, Qi,Wu, Shuwen,Xu, Zhichao,Zhang, Qiuhan,Zhou, Hai-Bing
, (2020/07/03)
Enterovirus A71 (EV-A71) is a human pathogen causing hand, foot and mouth disease (HFMD) which seriously threatened the safety and lives of infants and young children. However, there are no licensed direct antiviral agents to cure the HFMD. In this study, a series of quinoline formamide analogues as effective enterovirus inhibitors were developed, subsequent systematic structure-activity relationship (SAR) studies demonstrated that these quinoline formamide analogues exhibited good potency to treat EV-A71 infection. As described, the most efficient EV-A71 inhibitor 6i showed good anti-EV-A71 activity (EC50 = 1.238 μM) in RD cells. Furthermore, compound 6i could effectively prevent death of virus infected mice at dose of 6 mg/kg. When combined with emetine (0.1 mg/kg), this treatment could completely prevent the clinical symptoms and death of virus infected mice. Mechanism study indicated that compound 6i inhibited EV-A71 via targeting 2C helicase, thus impeding RNA remodeling and metabolism. Taken together, these data indicated that 6i is a promising EV-A71 inhibitor and worth extensive preclinical investigation as a lead compound.
Synthetic method of cinchocaine
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Paragraph 0020-0022; 0023-0025; 0026-0028, (2018/06/21)
The invention belongs to the technical field of pharmaceutical and chemical industry, in particular to a synthetic method of cinchocaine. The method comprises the following step of synthesizing 2-chloro-N-[2-(diethylamino)ethyl]-4-quinoline formamide, n-butyl alcohol and sodium hydroxide serving as raw materials to obtain the cinchocaine. The synthetic method has the advantages of high molar yield, low cost, safety, environmental friendliness and the like, and is more suitable for industrialization.
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