Morphine-N-oxide - Misplaced Pages

Morphine-N-oxide
Names

IUPAC name (4R,4aR,7S,7aR,12bS)-3-Methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methanobenzofuroisoquinoline-7,9-diol 3-oxide
Identifiers
CAS Number	639-46-3
3D model (JSmol)	Interactive image Interactive image
ChemSpider	4515047
ECHA InfoCard	100.010.324
EC Number	211-355-8
KEGG	C11786
PubChem CID	5362459
UNII	9E77NL2Y9I
CompTox Dashboard (EPA)	DTXSID301018237
InChI InChI=1S/C17H19NO4/c1-18(21)7-6-17-10-3-5-13(20)16(17)22-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-,18?/m0/s1Key: AMAPEXTUMXQULJ-APQDOHRLSA-N
SMILES CN1(=O)CC234Oc5c2c(C13C=C4O)ccc5O CN1(=O)CC234OC5=C(O)C=CC(C12C=C4O)=C35
Properties
Chemical formula	C₁₇H₁₉NO₄
Molar mass	301.342 g·mol
Legal status	BR: Class A1 (Narcotic drugs)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Morphine-N-oxide (genomorphine) is an active opioid metabolite of morphine. Morphine itself, in trials with rats, is 11–22 times more potent than morphine-N-oxide subcutaneously and 39–89 times more potent intraperitoneally. However, pretreatment with amiphenazole or tacrine increases the potency of morphine-N-oxide in relation to morphine (intraperitoneally more so than in subcutaneous administration). A possible explanation is that morphine-N-oxide is rapidly inactivated in the liver and impairment of inactivation processes or enzymes increases functionality.

Morphine-N-oxide can also form as a decomposition product of morphine outside the body and may show up in assays of opium and poppy straw concentrate. Codeine and the semi-synthetics such as heroin, dihydrocodeine, dihydromorphine, hydromorphone, and hydrocodone also have equivalent amine oxide derivatives.

Morphine-N-oxide has a DEA ACSCN of 9307 and annual production quota of 655 grams in 2013. It is a Schedule I controlled substance in the US.