7209. Phenampromid(e)

Nomenclature

CAS number: 129-83-9
N-[1-Methyl-2-(1-piperidinyl)ethyl]-N-phenylpropanamide; N-(1-methyl-2-piperidinoethyl)propionanilide; 1-piperidino-2-(N-propionylanilino)propane.
C17H26N2O; mol wt 274.40.
C 74.41%, H 9.55%, N 10.21%, O 5.83%.

Description and references

Prepn and analgesic activity: W. B. Wright, Jr. et al., J. Am. Chem. Soc. 81, 1518 (1959); W. B. Wright, Jr., H. J. Brabander, US 3016382 (1962 to Am. Cyanamid). (-)-Phenampromid(e), the more active enantiomer, has the R-configuration. Absolute configuration: Portoghese, J. Med. Chem. 8, 147 (1965). Pharmacology: Kikuchi et al., Nippon Yakurigaku Zasshi 57, 585 (1961), C.A. 59, 2082b (1963). Determn by HPLC: I. Jane, A. McKinnon, J. Chromatogr. 323, 191 (1985).

Chemical structure

Properties

Liquid, bp0.2 124-128°. nD28 1.518.

Derivative

(-)-Hydrochloride.
C17H27ClN2O; mol wt 310.86.
C 65.68%, H 8.75%, Cl 11.40%, N 9.01%, O 5.15%.

Properties

Crystals from alcoholic HCl + ether, mp 201-202°.

Note

This is a controlled substance (opiate): 21 CFR, 1308.11.