6520. Nicomorphine

Nomenclature

CAS number: 639-48-5
(5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol di-3-pyridinecarboxylate (ester); 3,6-dinicotinoylmorphine; morphine dinicotinate; morphine bis(pyridine-3-carboxylate).
C29H25N3O5; mol wt 495.53.
C 70.29%, H 5.09%, N 8.48%, O 16.14%.

Description and references

Semisynthetic opioid analgesic; morphine diester with nicotinic acid. Prepn: A. Pongratz, K. L. Zirm, Monatsh. Chem. 88, 330 (1957); GB 807115 (1959 to Lannacher Heilmittel). Pharmacology: K. L. Zirm, A. Pongratz, Arzneim.-Forsch. 9, 511 (1959). HPLC determn in serum: P. M. Koopman-Kimenai et al., J. Chromatogr. 416, 382 (1987). Clinical pharmacokinetics: idem et al., Eur. J. Anaesthesiol. 10, 125 (1993). Clinical trial for post-operative analgesia: M. Hasenbos et al., Acta Anaesthesiol. Scand. 29, 572, 577 (1985).

Chemical structure

Properties

Crystals, mp 178-178.5° (corr.). Practically insol in water. Sol in ethanol.

Derivative

Hydrochloride.

Nomenclature

CAS number: 12040-41-4
Vilan (Lannacher).
C29H25N3O5.HCl; mol wt 531.99.
C 65.47%, H 4.93%, N 7.90%, O 15.04%, Cl 6.66%.

Properties

Dec 248°. Sol in water with neutral reaction.

Note

This is a controlled substance (opium derivative): 21 CFR, 1308.11.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids; Phenanthrenes