4785. Hydrocodone

Nomenclature

CAS number: 125-29-1
(5α)-4,5-Epoxy-3-methoxy-17-methylmorphinan-6-one; dihydrocodeinone.
C18H21NO3; mol wt 299.36.
C 72.22%, H 7.07%, N 4.68%, O 16.03%.

Description and references

Semisynthetic opioid analgesic. Prepn from dihydrothebaine: M. Freund, E. Speyer, Ber. 53, 2250 (1920); by hydrogenation of codeinone: C. Mannich, H. Lwenheim, Arch. Pharm. 258, 295 (1920). Prepn from codeine: H. Rapoport et al., J. Org. Chem. 15, 1103 (1950); A. Stein, Pharmazie 10, 180 (1955). Asymmetric synthesis: C. Y. Hong et al., J. Am. Chem. Soc. 115, 11028 (1993); K. A Parker, D. Fokas, J. Org. Chem. 71, 449 (2006). LC/MS/MS determn in plasma: Y.-L. Chen et al., J. Chromatogr. B 769, 55 (2002). Pharmacology and toxicology: N. B. Eddy, J. G. Reid, J. Pharmacol. Exp. Ther. 52, 468 (1934). Evaluation of abuse liability: J. P. Zacny et al., Drug Alcohol Depend. 78, 243 (2005). Clinical comparison with oxycodone for acute pain: C. A. Marco et al., Acad. Emerg. Med. 12, 282 (2005).

Chemical structure

Properties

Prisms from alcohol, mp 197-198°. [α]D25 203° (c = 0.41 in CHCl3). Sol in alcohol, acetone, ethyl acetate, chloroform. Insol in water. uv max: 280 nm (ε 1310). LD50 s.c. in mice: 85.7 mg/kg (Eddy, Reid).

Derivative

Hydrochloride.

Nomenclature

CAS number: 25968-91-6
C18H21NO3.HCl; mol wt 335.83.
C 64.38%, H 6.60%, N 4.17%, O 14.29%, Cl 10.56%.

Properties

Monohydrate, crystals, mp 185-186° dec. [α]D27 130° (c = 2.877). Very sol in water.

Derivative

Bitartrate hemipentahydrate.

Nomenclature

CAS number: 34195-34-1; 143-71-5 (anhydrous)
Dicodid (tabl.) (Abbott); Hycodan (BMS).
C18H21NO3.C4H6O6.2H2O; mol wt 494.49.
C 53.44%, H 6.52%, N 2.83%, O 37.21%.

Properties

Component of Lortab, Vicodin, Vicoprofen, Zydone. Fine white crystals or crystalline powder. mp 118-128°. One gram dissolves in 16 ml water, in 150 g 95% ethanol. Almost insol in ether, chloroform. pH of a 2% aq soln about 3.6. Protect from light.

Note

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

Therapeutic Category

Analgesic; antitussive.

Keywords

Analgesic; Opioids; Phenanthrenes; Antitussive