Codeine-N-oxide

From Wikipedia, the free encyclopedia

Codeine-N-oxide

Systematic name (1S,4S,5R,13R,14S,17R)-10-Methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,13.0^5,17.0^7,18]octadeca-7(18),8,10,15-tetraen-14-ol 4-oxide
Identifiers
CAS number	3688-65-1
PubChem	5359929
ChemSpider	4514400
Jmol-3D images	{{#if:[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\|Image 1
SMILES [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
InChI 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
Properties
Molecular formula	C₁₈H₂₁NO₄
Molar mass	315.36 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

Codeine-N-oxide (genocodeine) is an active metabolite of codeine.^[1] It is an opiate listed as a Schedule I controlled substance.^[2]

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

Opioids

Opium and
poppy straw
derivatives

Crude opiate
extracts /
whole opium
products

Natural opiates

Opium alkaloids	Codeine Morphine Oripavine Pseudomorphine Thebaine

Alkaloid salts mixtures	Pantopon Papaveretum (Omnopon)

Semisynthetics
including
Bentley
compounds

Morphine family	2,4-Dinitrophenylmorphine 6-MDDM Azidomorphine Chlornaltrexamine Desocodeine Desomorphine Dihydromorphine Hydromorphinol Methyldesorphine N-Phenethylnormorphine RAM-378

3,6-diesters of morphine	Acetylpropionylmorphine Diacetyldihydromorphine Dibenzoylmorphine Dipropanoylmorphine Heroin Nicomorphine

Codeine-dionine family	6-Monoacetylcodeine Benzylmorphine Codeine methylbromide Ethylmorphine Heterocodeine Isocodeine Myrophine Pholcodine

Morphinones and morphols	14-Cinnamoyloxycodeinone 14-Ethoxymetopon 14-Methoxymetopon 14-Phenylpropoxymetopon 3-Acetyloxymorphone 3,14-Diacetyloxymorphone 6-MDDM 7-Spiroindanyloxymorphone Acetylmorphone Codeinone Codoxime Conorfone Hydrocodone Hydromorphone IBNtxA Methyldihydromorphine Metopon Morphinone N-Phenethyl-14-ethoxymetopon Nalmexone Oxycodone Oxymorphol Oxymorphone Pentamorphone Semorphone Thebacon

Morphides	α-Chlorocodide Chloromorphide

Dihydrocodeine series	14-Hydroxydihydrocodeine Acetyldihydrocodeine Dihydrocodeine Nicocodeine Nicodicodeine

Nitrogen morphine derivatives	Codeine-N-oxide Morphine-N-oxide

Hydrazones	Oxymorphazone

Halogenated morphine derivatives	1-Iodomorphine

Active opiate
metabolites

Morphinans

Benzomorphans

4-Phenylpiperidines

Pethidines (Meperidines)	4-Fluoropethidine 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 Isomethadone Levomethadone Methadone Normethadone Norpipanone Phenadoxone (Heptazone)

Methadols	Acetylmethadol Alphacetylmethadol Alphamethadol Betacetylmethadol Betamethadol Dimepheptanol (methadol) Isomethadol Levacetylmethadol Noracymethadol

Moramides	Desmethylmoramide Dextromoramide Levomoramide Moramide/Racemoramide

Thiambutenes	Diethylthiambutene Dimethylthiambutene Ethylmethylthiambutene Piperidylthiambutene Pyrrolidinylthiambutene Tipepidine

Phenalkoxams	Dextropropoxyphene Dimenoxadol Dioxaphetyl butyrate Levopropoxyphene Norpropoxyphene

Ampromides	Diampromide Phenampromide Propiram

Others	Alimadol IC-26 Isoaminile Lefetamine R-4066

Anilidopiperidines

Oripavine
derivatives

Phenazepanes

Pirinitramides

Benzimidazoles

Indoles

Diphenylmethyl-
piperazines

Opioid peptides

Others

Opioid
antagonists &
inverse agonists

Biased ligands

Uncategorized
opioids

List of opioids

This article is issued from Wikipedia. The text is available under the Creative Commons Attribution/Share Alike; additional terms may apply for the media files.