CODEINONE

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 Search

SMILES

[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]15CCN(C)[C@]([H])(C4)[C@]5([H])C=CC2=O

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

Approval Year

Targets

Primary Target	Pharmacology	Potency
apoptotic process 48 Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12894543	Activator 1430
NADPH-dependent codeinone reductase 1-1 2 Target ID: Q9SQ70 Gene ID: NA Gene Symbol: COR1.1 Target Organism: Papaver somniferum (Opium poppy) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10417697 \| https://www.ncbi.nlm.nih.gov/pubmed/29779229	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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17616524	Agonist 2678	294.0 nM [EC50]

PubMed

Title	Date	PubMed
Molecular characterization of the salutaridinol 7-O-acetyltransferase involved in morphine biosynthesis in opium poppy Papaver somniferum.	2001 Aug 17	11404355
Crystal structure of bacterial morphinone reductase and properties of the C191A mutant enzyme.	2002 Aug 23	12048188
Cell death-inducing activity of opiates in human oral tumor cell lines.	2002 Jan-Feb	12017290
Comparative analysis of apoptosis-inducing activity of codeine and codeinone.	2003 Mar	12606908
Analysis of apoptosis signaling pathway in human cancer cells by codeinone, a synthetic derivative of codeine.	2003 May-Jun	12894543
Electrospray tandem mass spectrometric investigations of morphinans.	2003 Nov	14597116
A tale of three cell types: alkaloid biosynthesis is localized to sieve elements in opium poppy.	2003 Nov	14508000
The toxicity of opiates and their metabolites in HepG2 cells.	2003 Oct 25	14597126
Developmental and inducible accumulation of gene transcripts involved in alkaloid biosynthesis in opium poppy.	2003 Sep	12946416
Putting the opium in poppy to sleep.	2004 Dec	15583658
RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy.	2004 Dec	15543134
6-oxo-morphinane oximes: pharmacology, chemistry and analytical application.	2004 Oct	15544463
Structural elucidation of chalcone reductase and implications for deoxychalcone biosynthesis.	2005 Aug 26	15970585
Silence of the poppies: a new source of drug precursors.	2005 Jan 1	15676290
Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment.	2005 May	15849302
14-Hydroxylation of opiates: catalytic direct autoxidation of codeinone to 14-hydroxycodeinone.	2005 May 25	15898757
Effect of anticancer agents on codeinone-induced apoptosis in human cancer cell lines.	2005 Nov-Dec	16309196
The role of phloem sieve elements and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy.	2006 Aug	16813579
Increasing morphinan alkaloid production by over-expressing codeinone reductase in transgenic Papaver somniferum.	2007 Jan	17207254
Linear-dichroic infrared spectral (IR-LD) analysis of codeine and its derivatives.	2007 May	17254838
Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors.	2007 Sep 14	17616524
14beta-Arylpropiolylamino-17-cyclopropylmethyl-7,8-dihydronormorphinones and related opioids. Further examples of pseudoirreversible mu opioid receptor antagonists.	2009 Nov 12	19842669

Patents

Name

Type

Language

CODEINONE

Common 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

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

OXYCODONE RELATED COMPOUND C

Common 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