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Cyclomethycaine

Cyclomethycaine Structure
Cyclomethycaine
  • CAS No.139-62-8
  • Chemical Name:Cyclomethycaine
  • CBNumber:CB51178400
  • Molecular Formula:C22H33NO3
  • Formula Weight:359.5
  • MOL File:139-62-8.mol
Cyclomethycaine Property
  • Boiling point 486.4±25.0 °C(Predicted)
  • Density 1.056±0.06 g/cm3(Predicted)
  • pka 9.40±0.10(Predicted)
  • FDA UNII 15E9I74NZ8
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements
  • Precautionary statements

Cyclomethycaine Chemical Properties,Usage,Production

  • Originator Surfacaine,Lilly,US,1948
  • Uses Cyclomethycaine is also used in topical anesthesia on the skin or mucous membranes for cuts, bites, and also for urological examinations. A common synonym of this drug is surfacaine.
  • Definition ChEBI: Cyclomethycaine is a benzoate ester.
  • Manufacturing Process 7.4 g of sodium are dissolved in 250 cc of isoamyl alcohol, 53 g of ethyl phydroxybenzoate are added and the mixture is heated to refluxing temperature for about 15 minutes. To the cooled mixture, 65 g of cyclohexyl bromide are added and the mixture is refluxed for about 3 hours. The isoamyl alcohol is removed by evaporation in vacuo and the residue is extracted with 10% aqueous sodium hydroxide solution to remove the unreacted ethyl phydroxybenzoate.
    The alkali-insoluble residue comprising ethyl p-cyclohexyloxybenzoate is hydrolyzed by refluxing with 10% sodium hydroxide solution for about 3 hours. The alkaline reaction mixture is acidified with hydrochloric acid whereupon p-cyclohexyloxybenzoic acid precipitates. The precipitate is separated by filtration, washed with water and dried. It melts at about 178° to 180°C. Yield: about 7%.
    62 g of p-cyclohexyloxybenozic acid and 49.5g of 3-(2'-methylpiperidino)- propyl chloride are dissolved in 300 cc of dry isopropanol and the mixture refluxed for about 12 hours. About half of the isopropanol is then distilled off and the residual solution cooled to about 0°C. 3(2'-methylpiperidino)-propyl p-cyclohexyloxybenzoate hydrochloride precipitates as a white crystalline compound. It is filtered off, washed once with ether and recrystallized from isopropanol.
    3(2'-Methylpiperidino)-propyl p-cyclohexyloxybenzoate hydrochloride thus prepared melted at about 178° to 180°C. Analysis showed the presence of 8.88% chlorine as compared with the calculated value of 8.96%.
  • brand name Surfacaine (Lilly).
  • Therapeutic Function Local anesthetic
  • Synthesis Cyclomethycaine, the ethyl ester of 3-(2-methylpiperidino)propyl-ocyclohexyloxybenzoic acid (2.3.4), is synthesized according to the figure below. Alkylation of 2-methylpiperidine with 3-chlorpropanol-1 gives 3-(2-methylpiperidino)propanol-1 (2.3.2), whose hydroxyl group is substituted by chlorine using thionyl chloride. The resulting 3-(2-methylpiperidino)propylchloride-1 (2.3.3) is further reacted with 4-cyclohexyloxybenzoic acid, which gives cyclomethycaine [27,28].

    Synthesis_139-62-8

Cyclomethycaine Preparation Products And Raw materials
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Cyclomethycaine Spectrum
139-62-8, CyclomethycaineRelated Search:
  • 环美卡因
  • 139-62-8
  • Cyclomethycaine USP/EP/BP
  • Cyclomethycaine
  • Benzoic acid,4-(cyclohexyloxy)-, 3-(2-methyl-1-piperidinyl)propyl ester
  • 4-(cyclohexoxy)benzoic acid 3-(2-methyl-1-piperidyl)propyl ester
  • 3-(2-methylpiperidin-1-yl)propyl 4-cyclohexyloxybenzoate
  • Topocaine
  • Surfathesin
  • Surfacaine
  • 4-(Cyclohexyloxy)benzoic acid 3-(2-methyl-1-piperidinyl)propyl

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