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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H19NO3
Molecular Weight 297.3484
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CODEINONE

SMILES

COC1=CC=C2C[C@@H]3[C@@H]4C=CC(=O)[C@@H]5OC1=C2[C@]45CCN3C

InChI

InChIKey=XYYVYLMBEZUESM-CMKMFDCUSA-N
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

HIDE SMILES / InChI
Molecular Formula C18H19NO3
Molecular Weight 297.3484
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1447
NADPH-dependent codeinone reductase 1-1
2
Target ID: Q9SQ70
Gene ID: NA
Gene Symbol: COR1.1
Target Organism: Papaver somniferum (Opium poppy)
Substrate
661
Mu-type opioid receptor
61
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
Agonist
2752
 294.0 nM [EC50]
PubMed

PubMed

TitleDatePubMed
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures.
2010-11-18
14beta-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and related opioids. Further examples of pseudoirreversible mu opioid receptor antagonists.
2009-11-12
Expression of Brugmansia candida Hyoscyamine 6beta-Hydroxylase gene in Saccharomyces cerevisiae and its potential use as biocatalyst.
2008-05-27
Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors.
2007-09-14
Linear-dichroic infrared spectral (IR-LD) analysis of codeine and its derivatives.
2007-05
Increasing morphinan alkaloid production by over-expressing codeinone reductase in transgenic Papaver somniferum.
2007-01
Induction of non-apoptotic cell death by morphinone in human promyelocytic leukemia HL-60 cells.
2006-11-11
Structural determinants of opioid activity in derivatives of 14-aminomorphinones: effects of changes to the chain linking of the C14-amino group to the aryl ring.
2006-10-05
Comparative transcript and alkaloid profiling in Papaver species identifies a short chain dehydrogenase/reductase involved in morphine biosynthesis.
2006-10
The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy.
2006-08
Effect of anticancer agents on codeinone-induced apoptosis in human cancer cell lines.
2005-11-29
Structural elucidation of chalcone reductase and implications for deoxychalcone biosynthesis.
2005-08-26
14-Hydroxylation of opiates: catalytic direct autoxidation of codeinone to 14-hydroxycodeinone.
2005-05-25
Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment.
2005-05
Silence of the poppies: a new source of drug precursors.
2005-01-01
Putting the opium in poppy to sleep.
2004-12
RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy.
2004-12
6-oxo-morphinane oximes: pharmacology, chemistry and analytical application.
2004-10
Electrospray tandem mass spectrometric investigations of morphinans.
2003-11
A tale of three cell types: alkaloid biosynthesis is localized to sieve elements in opium poppy.
2003-11
The toxicity of opiates and their metabolites in HepG2 cells.
2003-10-25
Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy.
2003-09
Analysis of apoptosis signaling pathway in human cancer cells by codeinone, a synthetic derivative of codeine.
2003-08-05
Comparative analysis of apoptosis-inducing activity of codeine and codeinone.
2003-03
Crystal structure of bacterial morphinone reductase and properties of the C191A mutant enzyme.
2002-08-23
Cell death-inducing activity of opiates in human oral tumor cell lines.
2002-05-23
Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum.
2001-08-17
Effects of glutathione and phenobarbital on the toxicity of codeinone.
1986-05-15
Patents

Patents

04140687
2
04272541
12
05869669
14
05922876
2
05948788
2
05952495
2
06008354
35
06008355
2
06013796
2
06090943
2
06235906
2
06365742
2
06946556
2
06958398
2
JP2004502637A
6
JP2010111656A
8
JPH1171375A
3
JPS5323998A
14
JPS5630980A
2
JPS5630981A
2
JPS59159790A
2
JPS60149589A
2
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:00:36 GMT 2025
Edited
by admin
on Mon Mar 31 22:00:36 GMT 2025
Record UNII
22B5AW0ANN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CODEINONE
Common Name English
OXYCODONE RELATED COMPOUND C
USP  
Preferred Name English
6-OXOCODEINE
Common Name English
6-CODEINONE
Common Name English
(-)-CODEINONE
Common Name English
CODEINE MONOHYDRATE IMPURITY I [EP IMPURITY]
Common Name English
OXYCODONE RELATED COMPOUND C CII
USP-RS  
Common Name English
MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, (5.ALPHA.)-
Systematic Name English
OXYCODONE RELATED COMPOUND C [USP-RS]
Common Name English
CODEINE HYDROCHLORIDE DIHYDRATE IMPURITY I [EP IMPURITY]
Common Name English
MORPHINAN-6-ONE, 7,8-DIDEHYDRO-4,5.ALPHA.-EPOXY-3-METHOXY-17-METHYL-
Systematic Name English
CODEINE PHOSPHATE HEMIHYDRATE IMPURITY I [EP IMPURITY]
Common Name English
HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY E [EP IMPURITY]
Common Name English
OXYCODONE RELATED COMPOUND C [USP IMPURITY]
Common Name English
Code System Code Type Description
RS_ITEM_NUM
1485238
Created by admin on Mon Mar 31 22:00:36 GMT 2025 , Edited by admin on Mon Mar 31 22:00:36 GMT 2025
PRIMARY
WIKIPEDIA
CODEINONE
Created by admin on Mon Mar 31 22:00:36 GMT 2025 , Edited by admin on Mon Mar 31 22:00:36 GMT 2025
PRIMARY
CAS
467-13-0
Created by admin on Mon Mar 31 22:00:36 GMT 2025 , Edited by admin on Mon Mar 31 22:00:36 GMT 2025
PRIMARY
EPA CompTox
DTXSID70196909
Created by admin on Mon Mar 31 22:00:36 GMT 2025 , Edited by admin on Mon Mar 31 22:00:36 GMT 2025
PRIMARY
ECHA (EC/EINECS)
207-386-1
Created by admin on Mon Mar 31 22:00:36 GMT 2025 , Edited by admin on Mon Mar 31 22:00:36 GMT 2025
PRIMARY
CHEBI
58473
Created by admin on Mon Mar 31 22:00:36 GMT 2025 , Edited by admin on Mon Mar 31 22:00:36 GMT 2025
PRIMARY
FDA UNII
22B5AW0ANN
Created by admin on Mon Mar 31 22:00:36 GMT 2025 , Edited by admin on Mon Mar 31 22:00:36 GMT 2025
PRIMARY
PUBCHEM
5459910
Created by admin on Mon Mar 31 22:00:36 GMT 2025 , Edited by admin on Mon Mar 31 22:00:36 GMT 2025
PRIMARY
CHEBI
18399
Created by admin on Mon Mar 31 22:00:36 GMT 2025 , Edited by admin on Mon Mar 31 22:00:36 GMT 2025
PRIMARY
Related Record Type Details
Structure of CODEINONE HYDROBROMIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of CODEINE ANHYDROUS
PARENT -> METABOLITE
Related Record Type Details
Structure of HYDROCODONE BITARTRATE
PARENT -> IMPURITY
Structure of OXYCODONE HYDROCHLORIDE
PARENT -> IMPURITY
Structure of CODEINE PHOSPHATE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of CODEINE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of CODEINE HYDROCHLORIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
NIH
NCATS
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