# Codeinone

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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 KEGG C06171 Y PubChem CID 5459910 UNII 22B5AW0ANN Y CompTox Dashboard (EPA) DTXSID70196909 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 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 verify (what is YN ?) Infobox references

Chemical compound

**Codeinone** is an isoquinolone alkaloid[1] found in the [opium poppy](/source/Opium_poppy).[2] As an analgesic, it is one-third the potency of [codeine](/source/Codeine). It is an important intermediate in the production of [hydrocodone](/source/Hydrocodone)–a painkiller about three-quarters the potency of morphine[*[citation needed](https://en.wikipedia.org/wiki/Wikipedia:Citation_needed)*]–as well as of [oxycodone](/source/Oxycodone),[3] though the latter can also be synthesized from [thebaine](/source/Thebaine).[4]

## Chemical structure

Codeinone can be described as the methylether of [morphinone](/source/Morphinone): 3-methyl-morphinone.

Codeinone can be also described as the [ketone](/source/Ketone) of [codeine](/source/Codeine): codeine-6-one.

## Apoptotic activity

Through renewed interest into possible anti-tumor activities of some of the [opium](/source/Opium) [alkaloids](/source/Alkaloid) 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*.[5]

## References

1. **[^](#cite_ref-CHEBI_1-0)** ["codeinone (CHEBI:18399)"](https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18399). *www.ebi.ac.uk*. Retrieved 28 October 2023.

1. **[^](#cite_ref-Lenz1995_2-0)** Lenz, Rainer; Zenk, Meinhart H. (April 1995). "Stereoselective reduction of codeinone, the penultimate enzymic step during morphine biosynthesis in Papaver somniferum". *Tetrahedron Letters*. **36** (14): 2449–2452. [doi](/source/Doi_(identifier)):[10.1016/0040-4039(95)00278-K](https://doi.org/10.1016%2F0040-4039%2895%2900278-K).

1. **[^](#cite_ref-3)** [Synthesis of Oxycodone from Codeine.](https://www.erowid.org/archive/rhodium/chemistry/oxycodone.html) Aug 2004 static snapshot of Rhodium site archive hosted by Erowid, May 2005

1. **[^](#cite_ref-4)** [Oxycodone / 14-hydroxydihydrocodeinone Synthesis; with alternative synthesis of 14-hydroxycodeinone intermediate.](https://www.scribd.com/doc/77193676/Oxycodone-Synthesis) J. Med. Chem., 1974, 17, 1117

1. **[^](#cite_ref-5)** Hitosugi, N; Nagasaka, H; Sakagami, H; Matsumoto, I; Kawase, M (2003). "Analysis of apoptosis signaling pathway in human cancer cells by codeinone, a synthetic derivative of codeine". *Anticancer Res*. **23** (3B): 2569–76. [PMID](/source/PMID_(identifier)) [12894543](https://pubmed.ncbi.nlm.nih.gov/12894543).

v t e Analgesics (N02A, N02B) Opioids Opiates/opium Codeine# +aspirin +paracetamol Morphine# (+naltrexone) Opium Laudanum Paregoric Semisynthetic Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Papaveretum Thebacon Synthetic Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl# (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone# NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tegileridine Tilidine Tramadol (+celecoxib, +paracetamol) Viminol Paracetamol-type Acetanilide‡ Bucetin‡ Butacetin‡ Paracetamol (acetaminophen)# +aspirin/caffeine +butalbital +codeine +hydrocodone +ibuprofen +metoclopramide +oxycodone +propyphenazone/caffeine +tramadol Parapropamol‡ Phenacetin‡ Propacetamol‡ NSAIDs Propionates Benoxaprofen ‡ Fenoprofen Flurbiprofen Ibuprofen# (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen Oxicams Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam Acetates Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac ‡ COX-2 inhibitors Celecoxib (+tramadol) Etoricoxib Lumiracoxib ‡ Parecoxib Rofecoxib ‡ Valdecoxib ‡ Fenamates Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid Salicylates Aspirin (acetylsalicylic acid)# (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate) Pyrazolones Aminophenazone‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine) Others Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone Cannabinoids Cannabidiol Cannabis Nabilone Nabiximols Tetrahydrocannabinol (dronabinol) Ion channel modulators Calcium blockers Alcohol (ethanol) Gabapentin Gabapentin enacarbil Leconotide Mirogabalin Pregabalin Ziconotide Sodium blockers Carbamazepine Lacosamide Local anesthetics (e.g., cocaine, lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g., amitriptyline#) Nav1.7/1.8-selective: DSP-2230§ Funapide§ PF-05089771§ Suzetrigine Potassium openers Flupirtine‡ Myorelaxants Carisoprodol Chlorzoxazone Cyclobenzaprine Mephenoxalone Methocarbamol Orphenadrine Others Analgecine Analgesic adjuvant Bedinvetmab Camphor Capsaicin Clonidine Frunevetmab Izenivetmab Ketamine Menthol Methoxyflurane Phenazopyridine Proglumide Relfovetmab Rimazolium Tanezumab #WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III

v t e Opioid receptor modulators μ-opioid (MOR) Agonists (abridged; full list) 3-HO-PCP 7-Acetoxymitragynine 7-Hydroxymitragynine ψ-Akuammigine α-Chlornaltrexamine α-Narcotine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin (metorphamide) AH-7921 Akuammicine Akuammidine Alfentanil Anileridine Apparicine β-Endorphin BAM-12P BAM-18P BAM-22P Benzhydrocodone Benzylmorphine Bezitramide Biphalin BU08070 Buprenorphine Butorphan Butorphanol Butyrfentanyl BW373U86 Carfentanil Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO (DAGO) Dermorphin Desmetramadol (desmethyltramadol) Desomorphine Deumitragynine 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 Lexanopadol Loperamide Loxicodegol LS-115509 Matrine MEB-1170 Meptazinol Met-enkephalin (metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine pseudoindoxyl Morphiceptin Morphine Nalbuphine Naloxone benzoylhydrazone (NalBzOH) Nalmexone Naltalimide Neopine NFEPP Nicocodeine Nicodicodine Nicomorphine Norketamine Nufenoxole Octreotide Oliceridine Oxycodegol (NKTR-181) Oxymorphone-3-methoxynaltrexonazine (OM-3-MNZ) Oripavine Oxycodone Oxymorphazone Oxymorphonazine Oxymorphone Oxymorphone phenylhydrazone OxyPNPH Papaver somniferum (opium) Pentazocine Pericine Pethidine (meperidine) Phenazocine Phencyclidine Piminodine Piritramide PL-017 Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil Salsolinol SC-17599 Sinomenine SR-17018 Sufentanil Susineridine Tapentadol Tetrahydropapaveroline TH-030418 Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 Tubotaiwine U-47700 Valorphin Viminol Xorphanol Antagonists (3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 3CS-nalmefene 4-Caffeoyl-1,5-quinide 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC α-Gliadin β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox CTAP CTOP Cyclofoxy Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Ginsenoside R Hyperoside Ibogaine JDTic Levallorphan Lobeline LY-255582 LY-2196044 Methocinnamox Methylnaltrexone Methylsamidorphan Naldemedine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Nalorphine dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexazone Naltrexonazine Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin δ-opioid (DOR) Agonists 3CS-nalmefene 6'-GNTI 7-SIOM ADL-5747 (PF-04856881) ADL-5859 Alazocine (SKF-10047) Amoxapine AR-M100390 (ARM390) AZD2327 β-Endorphin BAM-18P Biphalin BU-48 Butorphan Butorphanol BW373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin A Deltorphin I Deltorphin II Desmethylclozapine Desmetramadol (desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 DSLET Ethylketazocine Etorphine Fentanyl FIT Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone JNJ-20788560 KNT-127 Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lexanopadol Lofentanil Met-enkephalin (metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine NalBzOH Oripavine Oxycodone Oxymorphone Pethidine (meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SB-235863 SNC-80 SNC-162 TAN-67 (SB-205,607) TH-030418 Thebaine Thiobromadol (C-8813) Tonazocine Tramadol TRV250 Xorphanol Zenazocine Antagonists 4',7-Dihydroxyflavone 5'-NTII 6β-Naltrexol 6β-Naltrexol-d4 α-Santolol β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran BNTX Catechin Catechin gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin ICI-154129 ICI-174864 LY-255582 LY-2196044 Methylnaltrexone Methylnaltrindole N-Benzylnaltrindole Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SDM25N SoRI-9409 Taxifolin Thienorphine κ-opioid (KOR) Agonists 3CS-nalmefene 4-Allyl-6-oxa-noribogainalog 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin (metorphamide) Akuammicine Alazocine (SKF-10047) Allomatrine Apadoline Asimadoline BAM-12P BAM-18P BAM-22P 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 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 Levomethorphan Levorphanol Lexanopadol Lofentanil LPK-26 Lufuradom Matrine MB-1C-OH MEB-1170 Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine MR-2034 N-MPPP Nalbuphine NalBzOH Nalfurafine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Naltriben Niravoline Norbuprenorphine Norbuprenorphine-3-glucuronide Noribogaine Norketamine Oripavine Oxa-noribogaine 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-62066) TH-030418 Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50488 U-54494A U-69593 Xorphanol Antagonists 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone ANTI Apigenin Arodyne AT-076 Aticaprant Axelopran AZ-MTAB Binaltorphimine BU09059 Buprenorphine Catechin Catechin gallate CERC-501 (LY-2456302) Clocinnamox CVL-354 Cyclofoxy Dezocine DIPPA EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2196044 LY-2444296 LY-2459989 LY-2795050 MeJDTic Methylnaltrexone ML190 ML350 MR-2266 N-Fluoropropyl-JDTic Naloxone Naltrexone Naltrindole Naringenin Navacaprant Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 RU-24213 Quadazocine Taxifolin UPHIT Zyklophin Nociceptin (NOP) Agonists (Arg14,Lys15)Nociceptin ((pF)Phe4)Nociceptin(1-13)NH2 (Phe1Ψ(CH2-NH)Gly2)Nociceptin(1-13)NH2 Ac-RYYRWK-NH2 Ac-RYYRIK-NH2 BU08070 Buprenorphine Cebranopadol Dihydroetorphine Etorphine JNJ-19385899 Levomethorphan Levorphanol Lexanopadol MCOPPB MT-7716 NNC 63-0532 Nociceptin (orphanin FQ) Nociceptin (1-11) Nociceptin (1-13)NH2 Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 Ro65-6570 SCH-221510 SCH-486757 SR-8993 SR-16435 Sunobinop (S-117957) TH-030418 Antagonists (Nphe1)Nociceptin(1-13)NH2 AT-076 BAN-ORL-24 BTRX-246040 (LY-2940094) J-113397 JTC-801 NalBzOH Nociceptin (1-7) Nocistatin SB-612111 SR-16430 Thienorphine Trap-101 UFP-101 Others Enkephalinase inhibitors: Amastatin BL-2401 Candoxatril D-Phenylalanine Dexecadotril (retorphan) Ecadotril (sinorphan) Kelatorphan Racecadotril (acetorphan) RB-101 RB-120 RB-3007 Opiorphan Selank Semax Spinorphin Thiorphan Tynorphin Ubenimex (bestatin) Propeptides: β-Lipotropin (proendorphin) Prodynorphin Proenkephalin Pronociceptin Proopiomelanocortin (POMC) Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)

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Adapted from the Wikipedia article [Codeinone](https://en.wikipedia.org/wiki/Codeinone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Codeinone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.