Codeine-N-oxide
Codeine-N-oxide
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Names |
Systematic IUPAC name
(1S,4S,5R,13R,14S,17R)-10-Methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol 4-oxide |
Identifiers |
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3688-65-1 |
ChemSpider |
4514400 |
Jmol interactive 3D |
Image |
PubChem |
5359929 |
InChI=1S/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-,19-/m0/s1 Key: BDLSDHWCOJPHIE-KFUGMXNISA-N InChI=1/C18H21NO4/c1-19(21)8-7-18-11-4-5-13(20)17(18)23-16-14(22-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-,19-/m0/s1 Key: BDLSDHWCOJPHIE-KFUGMXNIBR
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[O-][N@@+]4([C@@H]3Cc5c1c(O[C@@H]2[C@]1([C@H]3/C=C\[C@@H]2O)CC4)c(OC)cc5)C
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Properties |
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C18H21NO4 |
Molar mass |
315.37 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Infobox references |
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Codeine-N-oxide (genocodeine) is an active metabolite of codeine.[1] It is an opiate listed as a Schedule I controlled substance.[2] It has a DEA ACSCN of 9053 and its annual manufacturing quota for 2013 was 602 grammes.
Like morphine-N-oxide, it was studied as a potential pharmaceutical drug and is considerably weaker than codeine. The amine oxides of this type form as oxidation products of the parent chemical; virtually every morphine/codeine class opioid has an equivalent nitrogen derivative such as hydromorphone-N-oxide.
References
- ↑ Phillipson, J. David; El-Dabbas, Samia W.; Gorrod, John W. (1978). "In vivo and in vitro N-oxidation of morphine and codeine". Biol. Oxid. Nitrogen, Proc. Int. Symp., 2nd: 125–30.
- ↑ 21 C.F.R. 1308.11
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| Receptor (ligands) | MOR |
- PAMs: BMS-986121
- BMS-986122
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| DOR | |
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| KOR |
- Agonists: 6'-GNTI
- 8-CAC
- 18-MC
- 14-Methoxymetopon
- β-Chlornaltrexamine
- β-Funaltrexamine
- Adrenorphin (metorphamide)
- Akuuamicine
- Alazocine
- Allomatrine
- Asimadoline
- BAM-12P
- BAM-18P
- BAM-22P
- Big dynorphin
- Bremazocine
- BRL-52537
- Butorphanol
- BW-373U86
- Cebranopadol
- Ciprefadol
- CR665
- Cyclazocine
- Cyclorphan
- Cyprenorphine
- Diamorphine (heroin)
- Diacetylnalorphine
- Difelikefalin
- Dihydroetorphine
- Dihydromorphine
- Dynorphin A
- Dynorphin B (rimorphin)
- Eluxadoline
- Enadoline
- Eptazocine
- Erinacine E
- Ethylketazocine
- Etorphine
- Fedotozine
- Fentanyl
- Gemazocine
- GR-89696
- GR-103545
- Hemorphin-4
- Herkinorin
- HS665
- Hydromorphone
- HZ-2
- Ibogaine
- ICI-199,441
- ICI-204,448
- Ketamine
- Ketazocine
- Laudanosine
- Leumorphin (dynorphin B-29)
- Levallorphan
- Levorphanol
- Lexanopadol
- Lofentanil
- LPK-26
- Lufuradom
- Matrine
- MB-1C-OH
- Menthol
- Metazocine
- Metkefamide
- Mianserin
- Mirtazapine
- Morphine
- Moxazocine
- MR-2034
- N-MPPP
- Nalbuphine
- NalBzOH
- Nalfurafine
- Nalmefene
- Nalorphine
- Naltriben
- Norbuprenorphine
- Norbuprenorphine-3-glucuronide
- Noribogaine
- Norketamine
- O-Desmethyltramadol
- Oripavine
- Oxilorphan
- Oxycodone
- Pentazocine
- Pethidine (meperidine)
- Phenazocine
- Proxorphan
- RB-64
- Salvinorin A (salvia)
- Salvinorin B ethoxymethyl ether
- Salvinorin B methoxymethyl ether
- SKF-10047
- Spiradoline (U-62,066)
- TH-030418
- Thienorphine
- Tifluadom
- Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline)
- U-50,488
- U-54,494A
- U-69,593
- Xorphanol
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| NOP | |
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| Unsorted / unknown | |
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| Enzyme (inhibitors) | |
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| Others |
- Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)
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| See also: Neuropeptidergics • Peptidergics |
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