Morphine-N-oxide
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IUPAC name (4R,4aR,7S,7aR,12bS)-3-Methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinoline-7,9-diol 3-oxide[citation needed] | |
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ECHA InfoCard | 100.010.324 ![]() |
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Chemical formula | C17H19NO4 |
Molar mass | 301.342 g·mol−1 |
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Except where otherwise noted, 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, 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.[2]
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.[3]
See also
- Codeine-N-oxide
- Morphine-6-glucuronide
- Morphine-3-glucuronide
References
- ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
- ^ Fennessy, M. R. (1968). "The analgesic action of morphine-n-oxide". British Journal of Pharmacology. 34 (2): 337–344. doi:10.1111/j.1476-5381.1968.tb07055.x. PMC 1703337. PMID 5687589.
- ^ 21 U.S.C. § 812(b)(1) United States Code via Cornell University's Legal Information Institute. Retrieved on 2024-10-01.
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Antagonists |
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- Enkephalinase inhibitors: Amastatin
- BL-2401
- Candoxatril
- D -Phenylalanine
- Dexecadotril (retorphan)
- Ecadotril (sinorphan)
- Kelatorphan
- Racecadotril (acetorphan)
- RB-101
- RB-120
- RB-3007
- Opiorphan
- Selank
- Semax
- Spinorphin
- Thiorphan
- Tynorphin
- Ubenimex (bestatin)
- Propeptides: β-Lipotropin (proendorphin)
- Prodynorphin
- Proenkephalin
- Pronociceptin
- Proopiomelanocortin (POMC)
- Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
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