12-03360. Diperodon Hydrochloride [Archived]

Nomenclature

CAS number: 537-12-2
3-(1-Piperidinyl)-1,2-propanediol bis(phenylcarbamate) (ester) monohydrochloride; 3-piperidino-1,2-propanediol dicarbanilate hydrochloride; 3-(1-piperidyl)-1,2-propanediol dicarbanilate hydrochloride; di(phenylurethan) of 1-piperidinepropane-2,3-diol hydrochloride; Diothane Hydrochloride (HMR); Proctodon (Rowell).
C22H28ClN3O4; mol wt 433.93.
C 60.89%, H 6.50%, Cl 8.17%, N 9.68%, O 14.75%.

Description and references

Prepn: T. H. Rider, J. Am. Chem. Soc. 52, 2115 (1930); idem, US 2004132 (1935). Stability of solns: E. S. Cook, T. H. Rider, J. Am. Pharm. Assoc. 26, 222 (1937). Pharmacology: eidem, J. Pharmacol. 64, 1 (1938). X-ray crystallographic study: R. C. Sullivan, K. P. O'Brien, Bull. Narc. 20, 31 (1968). IR spectra: eidem, ibid. 22, 35 (1970).

Chemical structure

Properties

Crystals. Bitter taste, followed by a sense of numbness. Stable in air at ordinary temps. Dec 195-200°. Sol in alcohol. Slightly sol in water (1:100), acetone and ethyl acetate. The aq soln is faintly acid to litmus. Extemporaneously prepd aq solns should be used promptly to avoid precipitation of the free base by traces of alkali. The soly in water is increased by the addn of sodium chloride. Insol in benzene or ether.

Therapeutic Category

Anesthetic (local).

Keywords

Anesthetic (Local)

Status

This monograph has been retired and is no longer subject to revision or update.