Morphine-N-oxide

Morphine-N-oxide: Morphine-N-oxide

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^Y

PubChem 5362459

ChemSpider 4515047^Y

EC number 211-355-8

KEGG C11786^Y

Jmol-3D images Image 1
Image 2

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

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^Y
Key: AMAPEXTUMXQULJ-APQDOHRLSA-N^Y

Properties

Molecular formula C₁₇H₁₉NO₄

Molar mass 301.34 g mol⁻¹

Exact mass 301.131408101 g mol⁻¹

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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 increase functionality.^[1]

See also

Morphine-6-glucuronide

Morphine-3-glucuronide

References

^ The analgesic action of morphine-N-oxide. M. R. Fennessy. Br J Pharmacol. 1968 October; 34(2): 337–344. PMCID: PMC1703337

v · d · eOpioids

Opium and
poppy straw
derivatives

Crude opiate extracts/
whole opium products

Compote/Kompot/Polish heroin • Diascordium • B & O Supprettes • Dover's powder • Kendal Black Drop • Laudanum • Mithridate • Opium • Paregoric • Poppy straw concentrate • Poppy tea • Smoking opium • Theriac

Natural opiates

Opium alkaloids
see also: Components of opium

Codeine • Morphine • Oripavine • Pseudomorphine • Thebaine

Alkaloid salts mixtures

Pantopon • Papaveretum (Omnopon)

Semisynthetics
including
Bentley compounds

Morphine family

2,4-Dinitrophenylmorphine • 6-Methylenedihydrodesoxymorphine • Chlornaltrexamine • Dihydrodesoxymorphine (Desomorphine) • Dihydromorphine • Hydromorphinol • Methyldesorphine • N-Phenethylnormorphine • RAM-378

3,6-diesters of morphine

Acetylpropionylmorphine • Diacetyldihydromorphine (Dihydroheroin, Acetylmorphinol) • Dibenzoylmorphine • Dipropanoylmorphine • Heroin (Diacetylmorphine) • Nicomorphine

Codeine-dionine family

6-Monoacetylcodeine • Benzylmorphine • Codeine methylbromide • Methyldihydromorphine (Dihydroheterocodeine) • Ethylmorphine (Dionine) • Heterocodeine • Morpholinylethylmorphine (Pholcodine) • Myrophine

Morphinones and morphols

14-Cinnamoyloxycodeinone • 14-Ethoxymetopon • 14-Methoxymetopon • 14-Phenylpropoxymetopon • 7-Spiroindanyloxymorphone • Acetylmorphone • Codeinone • Codorphone • Codoxime • Thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) • Hydrocodone • Hydromorphone • Metopon • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxycodone • Oxymorphol • Oxymorphone • Pentamorphone • Semorphone

Morphides

Chloromorphide

Dihydrocodeine series

14-hydroxydihydrocodeine • Acetyldihydrocodeine • Dihydrocodeine • Nicocodeine • Nicodicodeine

Nitrogen morphine derivatives

Morphine-N-Oxide

Hydrazones

Oxymorphazone

Halogenated morphine derivatives

1-Iodomorphine

Active opiate
metabolites

Morphine-6-glucuronide • 6-Monoacetylmorphine • Norcodeine • Normorphine

Morphinans

Morphinan series

Cyclorphan • Dextrallorphan • Levorphanol • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Methorphan / Racemethorphan • Morphanol / Racemorphanol • Ro4-1539 • Xorphanol

Others

Butorphanol • Cyprodime • Drotebanol • Nalbuphine • Sinomenine (Cocculine)

Benzomorphans

8-Carboxamidocyclazocine • Alazocine • Bremazocine • Dezocine • Ketazocine • Metazocine • Pentazocine • Phenazocine

4-Phenylpiperidines

Pethidines
(Meperidines)

4-Fluoromeperidine • Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine

Prodines

Allylprodine • Meprodine (α-meprodine / β-meprodine) • MPPP (Desmethylprodine) • PEPAP • Prodine (α-prodine / β-prodine) • Prosidol • Trimeperidine (Promedol)

Ketobemidones

Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone

Others
Alvimopan • Loperamide • Picenadol

Open chain
opioids

Amidones

Dipipanone • Methadone • Normethadone • Phenadoxone (Heptazone)

Methadols

Dimepheptanol (Racemethadol) • Levacetylmethadol

Moramides

Dextromoramide • Levomoramide • Racemoramide

Thiambutenes

Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Piperidylthiambutene • Pyrrolidinylthiambutene • Thiambutene • Tipepidine

Phenalkoxams

Dextropropoxyphene (Propoxyphene) • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Norpropoxyphene

Ampromides

Diampromide • Phenampromide • Propiram

Others

IC-26 • Isoaminile • Lefetamine • R-4066

Anilidopiperidines

3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • 4-Phenylfentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ocfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thiofentanyl • Trefentanil

Oripavine
derivatives

7-PET • Acetorphine • BU-48 • Buprenorphine • Cyprenorphine • Dihydroetorphine • Etorphine • Norbuprenorphine

Phenazepanes

Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine

Pirinitramides

Bezitramide • Piritramide

Benzimidazoles

Clonitazene • Etonitazene

Indoles

18-MC • 7-Hydroxymitragynine • Akuammine • Eseroline • Hodgkinsine • Mitragynine • Pericine

Diphenylmethylpiperazines

BW373U86 • DPI-221 • DPI-287 • DPI-3290 • SNC-80

Opioid peptides
see also: Opioid neuropeptides

Adrenorphin • Amidorphin • Casomorphin • DADLE • DAMGO • Dermorphin • Dynorphin • Endomorphin • Endorphins • Enkephalin • Gliadorphin • Morphiceptin • Nociceptin • Octreotide • Opiorphin • Rubiscolin • TRIMU 5

Others

AD-1211 • AH-7921 • Azaprocin • BDPC • BRL-52537 • Bromadoline • C-8813 • Ciramadol • Doxpicomine • Enadoline • Faxeladol • GR-89696 • Herkinorin • ICI-199,441 • ICI-204,448 • J-113,397 • JTC-801 • Ketamine • LPK-26 • Methopholine • MT-45 • N-Desmethylclozapine • NNC 63-0532 • Nortilidine • O-Desmethyltramadol • Phencyclidine • Prodilidine • Profadol • Ro64-6198 • Salvinorin A • SB-612,111 • SC-17599 • RWJ-394,674 • TAN-67 • Tapentadol • Tifluadom • Tilidine • Tramadol • Trimebutine • U-50,488 • U-69,593 • Viminol • W-18

Opioid antagonists
&
inverse agonists

5'-Guanidinonaltrindole • Alvimopan • Chlornaltrexamine • Cyclazocine • Cyprodime • Diprenorphine (M5050) • JDTic • Levallorphan • Methylnaltrexone • Nalfurafine • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Nalorphine • Naltrexol-d4 • Naltrexone • Naltriben • Naltrindole • Norbinaltorphimine • Oxilorphan

List of opioids

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Academic Dictionaries and Encyclopedias

Morphine-N-oxide

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References

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Morphine-N-oxide

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^Y
PubChem	5362459
ChemSpider	4515047^Y
EC number	211-355-8
KEGG	C11786^Y
Jmol-3D images	Image 1 Image 2
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
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^Y Key: AMAPEXTUMXQULJ-APQDOHRLSA-N^Y
Properties
Molecular formula	C₁₇H₁₉NO₄
Molar mass	301.34 g mol⁻¹
Exact mass	301.131408101 g mol⁻¹
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Academic Dictionaries and Encyclopedias

Wikipedia

Morphine-N-oxide

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References

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