139-62-8 Usage
Uses
Used in Medical Applications:
Cyclomethycaine is used as a topical anesthetic for various medical procedures, including treating minor cuts, insect bites, and other skin irritations. It provides rapid and effective pain relief by numbing the affected area, allowing for easier treatment and reduced discomfort.
Used in Urological Examinations:
In the field of urology, Cyclomethycaine is used as a local anesthetic during examinations and minor procedures. Its application helps to minimize pain and discomfort, making the examination process more tolerable for patients.
Used in Topical Anesthesia:
Cyclomethycaine is also used in topical anesthesia on the skin or mucous membranes for various medical applications. Its numbing effect is beneficial in providing pain relief and reducing discomfort during minor surgical procedures and other medical interventions.
Originator
Surfacaine,Lilly,US,1948
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%.
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].
Check Digit Verification of cas no
The CAS Registry Mumber 139-62-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 9 respectively; the second part has 2 digits, 6 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 139-62:
(5*1)+(4*3)+(3*9)+(2*6)+(1*2)=58
58 % 10 = 8
So 139-62-8 is a valid CAS Registry Number.
InChI:InChI=1/C22H33NO3/c1-18-8-5-6-15-23(18)16-7-17-25-22(24)19-11-13-21(14-12-19)26-20-9-3-2-4-10-20/h11-14,18,20H,2-10,15-17H2,1H3
