Normorphine

Normorphine

Clinical data
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) US: Schedule I
Identifiers
IUPAC name 3,6α-Dihydroxy-4,5α-epoxy-7,8-didehydromorphinan
Synonyms	Normorphine
CAS Number	466-97-7 Y
PubChem (CID)	5462508
IUPHAR/BPS	1630
ChemSpider	4575435 N
UNII	XUI1Y24IMI N
ECHA InfoCard	100.006.712
Chemical and physical data
Formula	C16H17NO3
Molar mass	271.311 g/mol
3D model (Jmol)	Interactive image
SMILES c1cc(c2c3c1C[C@@H]4[C@H]5[C@]3(CCN4)[C@@H](O2)[C@H](C=C5)O)O
InChI InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1 N Key:ONBWJWYUHXVEJS-ZTYRTETDSA-N N
NY (what is this?)  (verify)

Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s^[1] when a large group of N-substituted morphine analogues were characterized for activity. The compound has relatively little opioid activity in its own right,^[2][3] but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine.^[4] It is also a major metabolite of morphine,^[5] with its formation from morphine catalyzed by the liver enzymes CYP3A4 and CYP2C8.^[6]

Normorphine is a controlled substance listed under the Single Convention On Narcotic Drugs 1961 and the laws in various states implementing it; for example, in the United States it is a Schedule I Narcotic controlled substance, with an ACSCN of 9313 and an annual aggregate manufacturing quota of 18 grammes in 2014, unchanged from the prior year. The salts in use are the free base hexahydrate (free base conversion ratio 0.715), and hydrochloride (0.833).^[7]

References