Morphine-N-oxide

Morphine-N-oxide
Names
	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]
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/s1 Key: AMAPEXTUMXQULJ-APQDOHRLSA-N ;
	SMILES CN1(=O)CC[C@@]23[C@H]4Oc5c2c(C[C@@H]1[C@@H]3C=C[C@@H]4O)ccc5O; CN1(=O)CC[C@]23[C@H]4OC5=C(O)C=CC(C[C@@H]1[C@@H]2C=C[C@@H]4O)=C35;
Properties
Chemical formula	C17H19NO4
Molar mass	301.342 g·mol−1
Legal status	BR: Class A1 (Narcotic drugs);
	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]

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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]

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[1]
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.
[2]
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.
[3]
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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[1] [1]
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.

[2] [2]
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.

[3] [3]
21 U.S.C. § 812(b)(1) United States Code via Cornell University's Legal Information Institute. Retrieved on 2024-10-01.

[2]

[1]

[3]

Morphine-N-oxide

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References