Page last updated: 2024-11-11

6-codeinone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

6-codeinone: metabolite of codeine; RN given refers to (5alpha)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5459910
CHEMBL ID257627
CHEBI ID18399
SCHEMBL ID100655
MeSH IDM0134483

Synonyms (28)

Synonym
3-methoxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6-one
CHEBI:18399 ,
morphinan-6-one, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-alpha)-
6-codeinone
morphinan-6-one, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-
brn 0094188
einecs 207-386-1
codeinone ,
467-13-0
C06171
(5alpha)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-one
CHEMBL257627
22b5aw0ann ,
unii-22b5aw0ann
4-27-00-03599 (beilstein handbook reference)
6-oxocodeine
(-)-codeinone
hydrocodone hydrogen tartrate 2.5-hydrate impurity e [ep impurity]
morphinan-6-one, 7,8-didehydro-4,5.alpha.-epoxy-3-methoxy-17-methyl-
codeine hydrochloride dihydrate impurity i [ep impurity]
codeine phosphate hemihydrate impurity i [ep impurity]
codeine monohydrate impurity i [ep impurity]
morphinan-6-one, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5.alpha.)-
SCHEMBL100655
XYYVYLMBEZUESM-CMKMFDCUSA-N
DTXSID70196909
(4r,4ar,7ar,12bs)-9-methoxy-3-methyl-1,2,4,4a,7a,13-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
Q4918787

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The ability of sulfhydryl compounds to provide protection against the acute toxicity of codeinone, a toxic metabolite of codeine, was investigated in mice."( Effects of glutathione and phenobarbital on the toxicity of codeinone.
Inoue, K; Nagamatsu, K; Terao, T; Toki, S, 1986
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
isoquinoline alkaloidAny alkaloid that has a structure based on an isoquinoline nucleus. They are derived from the amino acids like tyrosine and phenylalanine.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorHomo sapiens (human)Ki0.45900.00000.419710.0000AID327878
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorHomo sapiens (human)EC50 (µMol)0.29400.00000.32639.4000AID327877
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerMu-type opioid receptorHomo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
sensory perceptionMu-type opioid receptorHomo sapiens (human)
negative regulation of cell population proliferationMu-type opioid receptorHomo sapiens (human)
sensory perception of painMu-type opioid receptorHomo sapiens (human)
G protein-coupled opioid receptor signaling pathwayMu-type opioid receptorHomo sapiens (human)
behavioral response to ethanolMu-type opioid receptorHomo sapiens (human)
positive regulation of neurogenesisMu-type opioid receptorHomo sapiens (human)
negative regulation of Wnt protein secretionMu-type opioid receptorHomo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeMu-type opioid receptorHomo sapiens (human)
calcium ion transmembrane transportMu-type opioid receptorHomo sapiens (human)
cellular response to morphineMu-type opioid receptorHomo sapiens (human)
regulation of cellular response to stressMu-type opioid receptorHomo sapiens (human)
regulation of NMDA receptor activityMu-type opioid receptorHomo sapiens (human)
neuropeptide signaling pathwayMu-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
G-protein alpha-subunit bindingMu-type opioid receptorHomo sapiens (human)
G protein-coupled receptor activityMu-type opioid receptorHomo sapiens (human)
beta-endorphin receptor activityMu-type opioid receptorHomo sapiens (human)
voltage-gated calcium channel activityMu-type opioid receptorHomo sapiens (human)
protein bindingMu-type opioid receptorHomo sapiens (human)
morphine receptor activityMu-type opioid receptorHomo sapiens (human)
G-protein beta-subunit bindingMu-type opioid receptorHomo sapiens (human)
neuropeptide bindingMu-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
endosomeMu-type opioid receptorHomo sapiens (human)
endoplasmic reticulumMu-type opioid receptorHomo sapiens (human)
Golgi apparatusMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
axonMu-type opioid receptorHomo sapiens (human)
dendriteMu-type opioid receptorHomo sapiens (human)
perikaryonMu-type opioid receptorHomo sapiens (human)
synapseMu-type opioid receptorHomo sapiens (human)
plasma membraneMu-type opioid receptorHomo sapiens (human)
neuron projectionMu-type opioid receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID327877Activation of human mu opioid receptor expressed in HEK293a cells co-expressing YFP-labelled alphai1 and CFP-labelled beta1gamma2 Gi subunits assessed as Gi protein activation by fluorescence resonance energy transfer2007The Journal of biological chemistry, Sep-14, Volume: 282, Issue:37
Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors.
AID327878Displacement of [3H]naloxone from human mu poioid receptor expressed in HEK293 cells2007The Journal of biological chemistry, Sep-14, Volume: 282, Issue:37
Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors.
AID327876Activation of human mu opioid receptor expressed in HEK293a cells coexpressing YFP-labelled alphai1 and CFP-labelled beta-1-gamma-2 Gi subunits assessed as decrease in fluorescence resonance energy transfer signal at 10 uM relative to morphine2007The Journal of biological chemistry, Sep-14, Volume: 282, Issue:37
Live cell monitoring of mu-opioid receptor-mediated G-protein activation reveals strong biological activity of close morphine biosynthetic precursors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (30.00)18.7374
1990's4 (40.00)18.2507
2000's3 (30.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.66

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.66 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.66)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]