Codeinone

Codeinone
Names

IUPAC name 3-Methoxy-17-methyl-7,8-didehydro-4,5α-epoxymorphinan-6-one
Preferred IUPAC name (4R,4aR,7aR,12bS)-9-Methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methano[1]benzofuro[3,2-e]isoquinolin-7-one
Identifiers
CAS Number	467-13-0^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18399^Y
ChEMBL	ChEMBL257627^Y
ChemSpider	4573639^Y
ECHA InfoCard	100.006.716
PubChem CID	5459910
UNII	22B5AW0ANN^Y
CompTox Dashboard (EPA)	DTXSID70196909
show InChI InChI=1S/C18H19NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-12,17H,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1^Y Key: XYYVYLMBEZUESM-CMKMFDCUSA-N^Y InChI=1/C18H19NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-12,17H,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1 Key: XYYVYLMBEZUESM-CMKMFDCUBF
show SMILES O=C1\C=C/[C@H]5[C@@H]4N(CC[C@@]52c3c(O[C@@H]12)c(OC)ccc3C4)C
Properties
Chemical formula	C₁₈H₁₉NO₃
Molar mass	297.35 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Codeinone is 1/3 as active as codeine as an analgesic but it is an important intermediate in the production of hydrocodone, a painkiller about 3/4 the potency of morphine;^{[citation needed]} as well as of oxycodone.^[1] The latter can also be synthesized from thebaine, however.^[2]

Chemical structure[]

Codeinone can be described as the methylether of morphinone: 3-methyl-morphinone.

Codeinone can be also described as the ketone of codeine: codeine-6-one.

Apoptotic activity[]

Through renewed interest into possible anti-tumor activities of some of the opium alkaloids and derivatives, unrelated to their antinociceptive properties and habit-forming effects, the oxidation product of codeine has been found to induce cell death in three different human cancer cell lines in vitro.^[3]

References[]

^ Synthesis of Oxycodone from Codeine. Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005
^ Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate. J. Med. Chem., 1974, 17, 1117
^ Hitosugi N, Nagasaka H, Sakagami H, Matsumoto I, Kawase M (2003). Anticancer Res. 23(3B):2569-76. PMID 12894543

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Analgesics (N02A, N02B)

show v t Opioid receptor modulators
MOR	Agonists (abridged; see here for a full list): 3-HO-PCP 7-Hydroxymitragynine α-Chlornaltrexamine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin (metorphamide) AH-7921 Akuammicine Alfentanil Anileridine Apparicine β-Endorphin Benzhydrocodone Benzylmorphine Bezitramide Biphalin Buprenorphine Butorphan Butorphanol Butyrfentanyl BW373U86 Carfentanil Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO (DAGO) Dermorphin Desmetramadol (desmethyltramadol) Desomorphine Dextromoramide Dextropropoxyphene (propoxyphene) Dezocine Dimenoxadol Dimethylaminopivalophenone Eluxadoline Diamorphine (heroin) Dihydrocodeine Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diphenoxylate Dipipanone Dynorphin A Embutramide Endomorphin-1 Endomorphin-2 Eseroline Ethylmorphine Etorphine Fentanyl Fluorophen Frakefamide Furanylfentanyl Hemorphin-4 Herkinorin Hodgkinsine Hydrocodone Hydromorphinol Hydromorphone IBNtxA Ketamine Ketobemidone Kratom Laudanosine Lefetamine Leu-enkephalin Levacetylmethadol Levomethorphan Levorphanol Loperamide LS-115509 Matrine Meptazinol Met-enkephalin (metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine pseudoindoxyl Morphiceptin Morphine Nalbuphine Nalmexone Naltalimide NFEPP Nicocodeine Nicodicodine Nicomorphine Norketamine Nufenoxole Octreotide Oliceridine OM-3-MNZ Oripavine Oxycodone Oxymorphazone Oxymorphone Papaver somniferum (opium) Pentazocine Pericine Pethidine (meperidine) Phenazocine Phencyclidine Piminodine Piritramide Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil SC-17599 Sinomenine Sufentanil Tapentadol Tetrahydropapaveroline Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 U-47700 Valorphin Viminol Xorphanol PAMs: Antagonists: (3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 4-Caffeoyl-1,5-quinide 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox CTAP Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Hyperoside Ibogaine Levallorphan Lobeline LY-255582 Methylnaltrexone Naldemedine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Nalorphine dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin Unknown/unsorted: Cannabidiol Coronaridine Cyproterone acetate Tabernanthine Tetrahydrocannabinol
DOR	Agonists: 6'-GNTI 7-SIOM Alazocine (SKF-10047) Amoxapine β-Endorphin Biphalin BU-48 Butorphan Butorphanol BW373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin A Deltorphin I Desmethylclozapine Desmetramadol (desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 Ethylketazocine Etorphine Fentanyl Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lofentanil Met-enkephalin (metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine Oripavine Oxycodone Oxymorphone Pethidine (meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SNC-80 TAN-67 (SB-205,607) Thebaine Thiobromadol (C-8813) Tonazocine Tramadol Xorphanol Zenazocine Antagonists: 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin LY-255582 Methylnaltrexone Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SoRI-9409 Taxifolin Thienorphine Unknown/unsorted: 18-MC Cannabidiol Coronaridine Cyproterone acetate Tabernanthine Tetrahydrocannabinol
KOR	Agonists: 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin (metorphamide) Alazocine (SKF-10047) Asimadoline Big dynorphin Bremazocine BRL-52537 Butorphan Butorphanol BW373U86 Cebranopadol Ciprefadol CR665 Cyclazocine Cyclorphan Cyprenorphine Desmetramadol (desmethyltramadol) Diamorphine (heroin) Diacetylnalorphine Difelikefalin Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diprenorphine Dynorphin A Dynorphin B (rimorphin) Eluxadoline Enadoline Eptazocine Ethylketazocine Etorphine Fedotozine Fentanyl Gemazocine GR-89696 Hemorphin-4 Herkinorin HS665 Hydromorphone HZ-2 Ibogaine ICI-199,441 ICI-204,448 Ketamine Ketazocine Laudanosine Leumorphin (dynorphin B-29) Levallorphan Levomethorphan Levorphanol Lofentanil LPK-26 Lufuradom Matrine Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine Nalbuphine Nalfurafine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Naltriben Niravoline Norbuprenorphine Norbuprenorphine-3-glucuronide Noribogaine Norketamine Oripavine Oxilorphan Oxycodone Pentazocine Pethidine (meperidine) Phenazocine Proxorphan Racemethorphan Racemorphan RB-64 Salvinorin A (salvia) Salvinorin B ethoxymethyl ether Salvinorin B methoxymethyl ether Samidorphan Spiradoline (U-62,066) Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50488 U-69,593 Xorphanol Antagonists: 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone Apigenin AT-076 Aticaprant Axelopran Binaltorphimine BU09059 Buprenorphine Catechin Catechin gallate CERC-501 (LY-2456302) Clocinnamox Dezocine EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2459989 Methylnaltrexone Naloxone Naltrexone Naltrindole Naringenin Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 Quadazocine Taxifolin Zyklophin Unknown/unsorted: Akuammicine Akuammine Coronaridine Cyproterone acetate Ibogamine Tabernanthine
NOP	Agonists: Buprenorphine Cebranopadol Dihydroetorphine Etorphine Levomethorphan Levorphanol MCOPPB NNC 63-0532 Nociceptin (orphanin FQ) Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 SR-16435 Antagonists: AT-076 BTRX-246040 (LY-2940094) J-113,397 JTC-801 SB-612,111 Thienorphine
Unsorted	β-Casomorphins Amidorphin Cytochrophin-4 Gliadorphin (gluteomorphin) Gluten exorphins Hemorphins Kava constituents NEM Neoendorphins Nepetalactone (catnip) Rubiscolins
Others	Enkephalinase inhibitors: Amastatin Candoxatril D -Phenylalanine Ecadotril (sinorphan) Kelatorphan Racecadotril (acetorphan) RB-101 RB-120 RB-3007 Selank Semax Spinorphin Thiorphan Tynorphin Ubenimex (bestatin) Propeptides: β-Lipotropin (proendorphin) Prodynorphin Proenkephalin Proopiomelanocortin (POMC) Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)

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