Morphine-N-oxide

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Morphine-N-oxide
Canonical, stereo, Kekulé, skeletal formula of morphine-N-oxide
Identifiers
CAS number 639-46-3 YesY
PubChem 5362459
ChemSpider 4515047 YesY
EC number 211-355-8
KEGG C11786 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C17H19NO4
Molar mass 301.34 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Morphine-N-oxide (genomorphine) is an active opioid metabolite of morphine. Morphine itself, in trials with rats, acts 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.[1]

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 diamorphine, 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 grammes in 2013. It is a Schedule I controlled substance in the US.[2]

See also[edit]

References[edit]

  1. ^ Fennessy, M. R. (1968). "The analgesic action of morphine-n-oxide". British journal of pharmacology 34 (2): 337–344. PMC 1703337. PMID 5687589. 
  2. ^ http://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm