7250. Phenoperidine
Nomenclature
CAS number: 562-26-5
1-(3-Hydroxy-3-phenylpropyl)-4-phenyl-4-piperidinecarboxylic
acid ethyl ester; 1-(3-hydroxy-3-phenylpropyl)-4-phenylisonipecotic acid ethyl
ester; 1-[γ-hydroxy-γ-phenylpropyl]-4-phenyl-4-carbethoxypiperidine; 3-(4-carbethoxy-4-phenylpiperidino)-1-phenyl-1-propanol; 1-phenyl-3-[(4′-phenyl-4′-carbethoxy)piperidino]-1-propanol; phenoperidin. C23H29NO3; mol wt 367.48.
C 75.17%, H 7.95%, N 3.81%, O 13.06%.
Description and references
Synthetic opioid analgesic; metabolized in vivo to meperidine, q.v. Prepn: P. A. J. Janssen, BE 576331 (1959); F. A. Cutler, Jr., J. F. Fisher, US 2962501 (1960 to Merck & Co.). Structure-activity study: P. A. J. Janssen, N. B. Eddy, J. Med. Pharm. Chem. 2, 31 (1960). Resolution, config, and activity of isomers: R. H. Mazur, J. Org. Chem. 26, 962 (1961). Crystal structure: C. Humblet et al., Acta Crystallogr. B34, 1389 (1978). GC determn in plasma: P. Kintz et al., Forensic Sci. Int. 43, 267 (1989).
Properties
Crystals from hot ethanol, mp 84-87°.Derivative
Hydrochloride.Nomenclature
CAS number: 3627-49-4
R-1406; Lealgin (Janssen); Operidine (Janssen). C23H29NO3.HCl; mol wt 403.94.
C 68.39%, H 7.49%, N 3.47%, O 11.88%, Cl 8.78%.
Properties
Crystals from ethyl acetate + methanol, or ethanol, mp 200-202°. Soluble in water.Derivative
l-Form.Properties
Glistening plates from aq methanol, mp 86-86.5°. [α]D -21°.Derivative
l-Form hydrochloride.Properties
Irregular prisms from isopropyl alcohol, mp 187-188°. [α]D -23°.Derivative
d-Form hydrochloride.Properties
mp 186-187°. [α]D +25°.Note
This is a controlled substance (opiate): 21 CFR, 1308.11.Therapeutic Category
Analgesic.
Keywords
Analgesic; Opioids; Phenylpiperidines