2735. Cyclomethycaine

Nomenclature

CAS number: 139-62-8
4-(Cyclohexyloxy)benzoic acid 3-(2-methyl-1-piperidinyl)propyl ester; p-cyclohexyloxybenzoic acid ester of N-(3-hydroxypropyl)pipecoline; 3-(2-methylpiperidino)propyl p-cyclohexyloxybenzoate; Surfacaine (Lilly); Surfathesin; Topocaine (Lilly).
C22H33NO3; mol wt 359.50.
C 73.50%, H 9.25%, N 3.90%, O 13.35%.

Description and references

Prepn: McElvain, Carney, J. Am. Chem. Soc. 68, 2592 (1946), eidem, US 2439818 (1948). Toxicity data: Schmidt et al., Toxicol. Appl. Pharmacol. 1, 454 (1959).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 537-61-1
C22H33NO3.HCl; mol wt 395.96.
C 66.73%, H 8.65%, N 3.54%, O 12.12%, Cl 8.95%.

Properties

Crystals, dec 178-180°. Soly in water: slightly >1 g/100 ml.

Derivative

Sulfate.
(C22H33NO3)2.H2SO4; mol wt 817.08.
C 64.68%, H 8.39%, N 3.43%, O 19.58%, S 3.92%.

Properties

Crystals, mod sol in water.

Therapeutic Category

Topical anesthetic.

Therapeutic Category (Veterinary)

Surface anesthetic.

Keywords

Anesthetic (Local)