6959. Oxycodone

Nomenclature

CAS number: 76-42-6
(5α)-4,5-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one; 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine; dihydrohydroxycodeinone; 14-hydroxydihydrocodeinone; Dihydrone.
C18H21NO4; mol wt 315.36.
C 68.55%, H 6.71%, N 4.44%, O 20.29%.

Description and references

Semisynthetic opioid analgesic. Prepn from thebaine: M. Freund, E. Speyer, J. Prakt. Chem. 94, 135 (1916); R. Krassnig et al., Arch. Pharm. 329, 325 (1996); from codeine: A. J. Walker, N. C. Bruce, Tetrahedron 60, 561 (2004). Bibliography: Small, Lutz, “Chemistry of the Opium Alkaloids,” Suppl. No. 103 to Public Health Reports, Washington (1932); K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954). In vitro liposolubility and protein binding: R. P"oyhi"a, T. Sepp"al"a, Pharmacol. Toxicol. 74, 23 (1994). HPLC determn in serum: A. W. E. Wright et al., J. Chromatogr. B 712, 169 (1998). Review of pharmacokinetics and clinical experience: E. Kalso, J. Pain Symptom Manage. 29, S47-S56 (2005); of abuse potential: T. J. Cicero et al., J. Pain 6, 662-672 (2005).

Chemical structure

Properties

Long rods from alc, mp 218-220°. pKa 8.53. Sol in alcohol, chloroform. Nearly insol in ether, water, KOH, NaOH, NH4OH.

Derivative

Hydrochloride.

Nomenclature

CAS number: 124-90-3
Dinarkon (Biotika); Eubine (Chiesi); Eukodal (Merck KGaA); OxyContin (Purdue); Oxygesic (Mundipharma); Oxynorm (Mundipharma); Supeudol (Sabex).
C18H21NO4.HCl; mol wt 351.82.
C 61.45%, H 6.30%, N 3.98%, O 18.19%, Cl 10.08%.

Properties

Component of Percocet and Percodan. Long rods from water, dec 270-272°. [α]D20 -125° (c = 2.5). Partition coefficient (octanol/water): 0.7. One gram dissolves in 6-7 ml water. Slightly sol in alcohol.

Derivative

Pectinate.

Nomenclature

CAS number: 9012-92-4
Proladone (Abbott).

Properties

Used for prolonged action.

Note

This is a controlled substance (opiate): 21 CFR, 1308.12.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids; Phenanthrenes