5849. Meperidine
Nomenclature
CAS number: 57-42-1
1-Methyl-4-phenyl-4-piperidinecarboxylic acid ethyl ester; 1-methyl-4-phenylisonipecotic acid ethyl ester; N-methyl-4-phenyl-4-carbethoxypiperidine; ethyl 1-methyl-4-phenylpiperidine-4-carboxylate; isonipecaine; pethidine. C15H21NO2; mol wt 247.33.
C 72.84%, H 8.56%, N 5.66%, O 12.94%.
Description and references
Opioid analgesic. Prepn: Eisleb, US 2167351 (1939 to Winthrop); Smissman, Hite, J. Am. Chem. Soc. 81, 1201 (1959). Pharmacokinetics: L. E. Mather, P. J. Meffin, Clin. Pharmacokinet. 3, 352 (1978). Metabolism: S. Y. Yeh et al., J. Pharm. Sci. 70, 867 (1981). GC-MS/MS determn in biological fluids: A. Ishii et al., J. Chromatogr. B 792, 117 (2003). Toxicity data: O. W. Barlow, J. R. Lewis, J. Pharmacol. Exp. Ther. 103, 147 (1951). Comprehensive description: N. P. Fish, N. J. DeAngelis in Anal. Profiles Drug Subs. 1, 175-205 (1972).
Derivative
Hydrochloride.Nomenclature
CAS number: 50-13-5
Algil (Maggioni); Alodan (Gerot); Centralgin (Amino); Demerol hydrochloride (Sanofi Winthrop); Dispadol (Specia); Dolantin (HMR); Dolestine (Teva); Dolosal (Specia); Mefedina (Farmitalia). C15H21NO2.HCl; mol wt 283.79.
C 63.48%, H 7.81%, N 4.94%, O 11.28%, Cl 12.49%.
Properties
Minute crystals, mp 186-189°. Slightly bitter taste. Stable to air. Just acid to litmus (1:10 soln). Sol in water, acetone, ethyl acetate; slightly sol in alcohol, isopropanol. Insol in benzene, ether. Aq solns may be sterilized by boiling for short periods without dec. LD50 orally in rats: 170 mg/kg (Barlow, Lewis).Note
This is a controlled substance (opiate): 21 CFR, 1308.12.Therapeutic Category
Analgesic.
Therapeutic Category (Veterinary)
Analgesic; sedative; anesthetic.Keywords
Analgesic; Opioids; Phenylpiperidines