Page last updated: 2024-11-11

oripavine

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

Description

oripavine: from, Papaver orientale L. & P. bacterium Lindl; structure in Merck Index, 9th ed, #6707; RN given refers to (5alpha)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

oripavine : A morphinane alkaloid with formula C18H19NO3. It is the major metabolite of thebaine. [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]

FloraRankFlora DefinitionFamilyFamily Definition
PapavergenusA genus of Eurasian herbaceous plants, the poppies (family PAPAVERACEAE of the dicotyledon class Magnoliopsida), that yield OPIUM from the latex of the unripe seed pods.[MeSH]PapaveraceaeThe poppy plant family of the order Papaverales, subclass Magnoliidae, class Magnoliopsida. These have bisexual, regular, cup-shaped flowers with one superior pistil and many stamens; 2 or 3 conspicuous, separate sepals and a number of separate petals. The fruit is a capsule. Leaves are usually deeply cut or divided into leaflets.[MeSH]
Papaver orientalespecies[no description available]PapaveraceaeThe poppy plant family of the order Papaverales, subclass Magnoliidae, class Magnoliopsida. These have bisexual, regular, cup-shaped flowers with one superior pistil and many stamens; 2 or 3 conspicuous, separate sepals and a number of separate petals. The fruit is a capsule. Leaves are usually deeply cut or divided into leaflets.[MeSH]

Cross-References

ID SourceID
PubMed CID5462306
CHEMBL ID437602
CHEBI ID7782
SCHEMBL ID37889
SCHEMBL ID19880919
MeSH IDM0046724

Synonyms (33)

Synonym
467-04-9
6,7,8,14-tetradehydro-4,5-alpha-epoxy-6-methoxy-17-methyl-morphinan-3-ol
einecs 207-385-6
morphinan-3-ol, 6,7,8,14-tetradehydro-4,5-alpha-epoxy-6-methoxy-17-methyl-
(5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methylmorphinan-3-ol
brn 0046094
C06175
oripavine
chebi:7782 ,
CHEMBL437602
3-o-demethylthebaine
unii-575aou51cr
dea no. 9330
4-27-00-02270 (beilstein handbook reference)
575aou51cr ,
hsdb 8324
morphine hydrochloride impurity c [ep impurity]
ids-no-010
6,7,8,14-tetradehydro-4,5.alpha.-epoxy-6-methoxy-17-methylmorphinan-3-ol
oripavine [mi]
codeine monohydrate impurity l [ep impurity]
codeine hydrochloride dihydrate impurity l [ep impurity]
codeine phosphate hemihydrate impurity l [ep impurity]
morphine sulfate impurity c [ep impurity]
morphinan-3-ol, 6,7,8,14-tetradehydro-4,5-epoxy-6-methoxy-17-methyl-, (5.alpha.)-
ZKLXUUYLEHCAMF-UUWFMWQGSA-N
SCHEMBL37889
SCHEMBL19880919
DTXSID10196908
oripavine 0.1 mg/ml in methanol
6,7,8,14-tetradehydro-4,5alpha-epoxy-6-methoxy-17-methylmorphinan-3-ol (oripavine)
Q420639
(1s,5r,13r)-14-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0?,??.0?,??.0?,??]octadeca-7,9,11(18),14,16-pentaen-10-ol

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Toxic signs of oripavine and phi-dihydrothebaine in both species were clonic-tonic convulsions followed by death."( Analgesic activity and toxicity of oripavine and phi-dihydrothebaine in the mouse and rat.
Yeh, SY, 1981
)
0.89
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
opioid analgesicA narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
bacterial xenobiotic metaboliteAny bacterial metabolite produced by metabolism of a xenobiotic compound in bacteria.
[role 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]

Drug Classes (5)

ClassDescription
morphinane alkaloidAn isoquinoline alkaloid based on a morphinan skeleton and its substituted derivatives.
organic heteropentacyclic compound
tertiary amino compoundA compound formally derived from ammonia by replacing three hydrogen atoms by organyl groups.
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
organic hydroxy compoundAn organic compound having at least one hydroxy group attached to a carbon atom.
[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]

Pathways (1)

PathwayProteinsCompounds
morphine biosynthesis234

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorHomo sapiens (human)Ki0.28600.00000.419710.0000AID327878
[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)0.27700.00000.32639.4000AID327877
[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
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.
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.
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 (29)

TimeframeStudies, This Drug (%)All Drugs %
pre-199012 (41.38)18.7374
1990's3 (10.34)18.2507
2000's6 (20.69)29.6817
2010's7 (24.14)24.3611
2020's1 (3.45)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.38

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index36.38 (24.57)
Research Supply Index3.40 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index50.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.38)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.45%)6.00%
Case Studies1 (3.45%)4.05%
Observational0 (0.00%)0.25%
Other27 (93.10%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]