3171. Dihydrocodeine

Nomenclature

CAS number: 125-28-0
(5α,6α)-4,5-Epoxy-3-methoxy-17-methylmorphinan-6-ol; 6-hydroxy-3-methoxy-N-methyl-4,5-epoxymorphinan; dihydroneopine; drocode.
C18H23NO3; mol wt 301.38.
C 71.73%, H 7.69%, N 4.65%, O 15.93%.

Description and references

Semisynthetic opioid analgesic; metabolized to dihydromorphine, q.v., by cytochrome P450 2D6. Prepd by reduction of codeine or neopine: Skita, Franck, Ber. 44, 2862 (1911); Wieland, Koralek, Ann. 433, 269 (1923); Stein, Pharmazie 10, 180 (1955). GC-MS determn in urine: M. Balikova et al., J. Chromatogr. B 752, 179 (2001). Metabolism in humans: M. F. Fromm et al., Clin. Pharmacol. Ther. 58, 374 (1995). Clinical pharmacokinetics: S. Ammon et al., Br. J. Clin. Pharmacol. 48, 317 (1999). Opioid receptor binding profile: H. Schmidt et al., Pharmacol. Toxicol. 91, 57 (2002). Clinical trial in chronic pain: C. H. Wilder-Smith et al., Pain 91, 23 (2001); in maintenance treatment of opioid dependence: J. R. Robertson et al., Addiction 101, 1752 (2006).

Chemical structure

Properties

Crystals from methanol + water, mp 112-113°; bp15 248°.

Derivative

Tartrate.

Nomenclature

CAS number: 5965-13-9
Dihydrocodeine bitartrate; Codicontin (Mundipharma); DF 118 (Aspen); DHC (Mundipharma); Dicodin (Mundipharma); Paracodin (Abbott); Parzone (Mallinckrodt); Tiamon (Temmler).
C18H23NO3.C4H6O6; mol wt 451.47.
C 58.53%, H 6.47%, N 3.10%, O 31.89%.

Properties

Crystals from methanol, contains 66.8% dihydrocodeine when completely anhydr. mp 192-193° (Stein). [α]D25 -72 to -75° (c = 1 in H2O). One gram dissolves in 4.5 ml water. Sparingly sol in alcohol. Insol in ether.

Note

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

Therapeutic Category

Analgesic; antitussive.

Keywords

Antitussive; Analgesic; Opioids; Phenanthrenes