6711. Normorphine
Nomenclature
CAS number: 466-97-7;
6035-32-1
(sesquihydrate)
(5α,6α)-7,8-Didehydro-4,5-epoxymorphinan-3,6-diol; desmethylmorphine. C16H17NO3; mol wt 271.31.
C 70.83%, H 6.32%, N 5.16%, O 17.69%.
Description and references
Opioid analgesic; minor, bioactive metabolite of morphine, q.v. Prepn: I. J. von Braun et al., Ber. 47, 2312 (1914); DE 286743 (1914 to Hoffmann-La Roche); E. Speyer, L. Walther, Ber. 63, 852 (1930); J. Weijlard, A. E. Erickson, J. Am. Chem. Soc. 64, 869 (1942); M. M. Abdel-Monem, P. S. Portoghese, J. Med. Chem. 15, 208 (1975). Characterization as morphine metabolite: U. Boerner et al., J. Pharm. Pharmacol. 26, 393 (1974). Formation by cytochrome P450 isoenzymes: D. Projean et al., Xenobiotica 33, 841 (2003). GC-MS determn in urine: C. Meadway et al., Forensic Sci. Int. 127, 136 (2002).
Properties
Crystals from chloroform + isopropanol, mp 277°. Sesquihydrate, crystals from water, mp 272-273°. Sparingly sol in hot water, alcohol. Insol in ether, chloroform.Derivative
Hydrochloride.Nomenclature
CAS number: 3372-02-9
C16H17NO3.HCl; mol wt 307.77.
C 62.44%, H 5.89%, N 4.55%, O 15.60%, Cl 11.52%.