Page last updated: 2024-12-11

thebaine

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

Description

Thebaine: A drug that is derived from opium, which contains from 0.3-1.5% thebaine depending on its origin. It produces strychnine-like convulsions rather than narcosis. It may be habit-forming and is a controlled substance (opiate) listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.12 (1985). (From Merck Index, 11th ed) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5324289
CHEMBL ID403893
CHEBI ID9519
SCHEMBL ID37580
SCHEMBL ID19880976
MeSH IDM0021272

Synonyms (48)

Synonym
einecs 204-084-1
morphinan, 6,7,8,14-tetradehydro-4,5-alpha-epoxy-3,6-dimethoxy-17-methyl-
thebain
dea no. 9333
CHEBI:9519 ,
4,5alpha-epoxy-3,6-dimethoxy-17-methyl-6,8-morphinadien
(5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan
(5r,9r,13s)-4,5-epoxy-3,6-dimethoxy-9alpha-methyl-6,8-morphinadien
3-o-methyl-oripavin
paramorphine
3,6-dimethoxy-17-methyl-6,7,8,14-tetradehydro-4,5alpha-epoxymorphinan
115-37-7
thebaine
C06173
thebaine, powder
NCGC00160239-01
CHEMBL403893
cas-115-37-7
tox21_111751
tox21_112863
dtxcid5026099
dtxsid7046099 ,
2p9mkg8gx7 ,
unii-2p9mkg8gx7
thebaine [who-dd]
codeine phosphate sesquihydrate impurity g [ep impurity]
codeine hydrochloride dihydrate impurity g [ep impurity]
(5.alpha.)-6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan
ids-nt-002
codeine monohydrate impurity g [ep impurity]
oxycodone hydrochloride impurity f [ep impurity]
hydrocodone hydrogen tartrate 2.5-hydrate impurity i [ep impurity]
codeine phosphate hemihydrate impurity g [ep impurity]
thebaine [mi]
FQXXSQDCDRQNQE-VMDGZTHMSA-N
SCHEMBL37580
SCHEMBL19880976
thebaine, european pharmacopoeia (ep) reference standard
thebaine 0.1 mg/ml in methanol
kodein
bdbm224032
D4R ,
Q63392872
6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan
tebaine
(4r,7ar,12bs)-7,9-dimethoxy-3-methyl-2,4,7a,13-tetrahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline
morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-,(5.alpha.)-
thebaine, 1mg/ml in methanol

Research Excerpts

Overview

Thebaine is a precursor in the formation of endogenous morphine and codeine in man, being O-demethylated to oripavine. Thebaine can be found in poppy seeds in relatively high concentrations.

ExcerptReferenceRelevance
"Thebaine is an alkaloid and can be found in poppy seeds in relatively high concentrations. "( In vitro evaluation of chromosomal damage and DNA strand breaks after treatment with the poppy seed alkaloid thebaine.
Bankoglu, EE; Hintzsche, H; Reimann, H; Stopper, H,
)
1.79
"Thebaine is an opium alkaloid that has been shown to be present in the urine of individuals who have consumed poppy seeds, as well as those who have used opium."( Urine thebaine determination by liquid chromatography tandem mass spectrometry after poppy seed consumption.
Banks, JF; Bollini, SM; Hobbs, GA, 2022
)
1.92
"Thebaine is a precursor in the formation of endogenous morphine and codeine in man, being O-demethylated to oripavine."( Thebaine O-demethylation to oripavine: genetic differences between two rat strains.
Bochner, F; Eichelbaum, M; Mikus, G; Somogyi, AA, 1991
)
2.45

Actions

ExcerptReferenceRelevance
"Thebaine did not produce any morphine-like effects in nondependent dogs nor did it precipitate an abstinence syndrome in morphine-dependent dogs."( The pharmacology of thebaine in the chronic spinal dog.
Gilbert, PE; Martin, WR, 1978
)
1.3

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
)
0.77

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
" Nevertheless, thebaine and related derivatives are often insoluble in aqueous media and have low bioavailability in digestive systems."( Micronization of Thebaine Extracted from Papaver bracteatum Lindl. Using Supercritical Fluid Technology.
Karimi, M; Raofie, F; Salehi, H, 2022
)
1.41
" This process led to improved oral bioavailability of alkaloids."( Micronization of Thebaine Extracted from Papaver bracteatum Lindl. Using Supercritical Fluid Technology.
Karimi, M; Raofie, F; Salehi, H, 2022
)
1.06
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
morphinane alkaloidAn isoquinoline alkaloid based on a morphinan skeleton and its substituted derivatives.
organic heteropentacyclic compound
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency61.42620.000221.22318,912.5098AID743036
estrogen nuclear receptor alphaHomo sapiens (human)Potency19.42470.000229.305416,493.5996AID743075
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency46.33750.000323.4451159.6830AID743065; AID743067
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Mu-type opioid receptorHomo sapiens (human)Ki7.40000.00000.419710.0000AID327878
[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)5.60000.00000.32639.4000AID327877
Mas-related G-protein coupled receptor member X2Homo sapiens (human)EC50 (µMol)32.66670.14003.73818.9000AID1802708; AID1802709
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (21)

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)
sensory perception of painMas-related G-protein coupled receptor member X2Homo sapiens (human)
sleepMas-related G-protein coupled receptor member X2Homo sapiens (human)
positive regulation of cytokinesisMas-related G-protein coupled receptor member X2Homo sapiens (human)
mast cell degranulationMas-related G-protein coupled receptor member X2Homo sapiens (human)
mast cell activationMas-related G-protein coupled receptor member X2Homo sapiens (human)
G protein-coupled receptor signaling pathwayMas-related G-protein coupled receptor member X2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

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)
G protein-coupled receptor activityMas-related G-protein coupled receptor member X2Homo sapiens (human)
neuropeptide bindingMas-related G-protein coupled receptor member X2Homo sapiens (human)
mast cell secretagogue receptor activityMas-related G-protein coupled receptor member X2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

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)
membraneMas-related G-protein coupled receptor member X2Homo sapiens (human)
plasma membraneMas-related G-protein coupled receptor member X2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID504749qHTS profiling for inhibitors of Plasmodium falciparum proliferation2011Science (New York, N.Y.), Aug-05, Volume: 333, Issue:6043
Chemical genomic profiling for antimalarial therapies, response signatures, and molecular targets.
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.
AID327875Activation of human mu opioid receptor expressed in HEK293a cells co-expressing YFP-labelled alphai1 and CFP-labelled beta1gamma2 Gi subunits assessed as decrease in fluorescence resonance energy transfer signal at 100 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.
AID1802708Intracellular Calcium Mobilization Assay from Article 10.1038/nchembio.2334: \\In silico design of novel probes for the atypical opioid receptor MRGPRX2.\\2017Nature chemical biology, 05, Volume: 13, Issue:5
In silico design of novel probes for the atypical opioid receptor MRGPRX2.
AID1802709PRESTO-Tango Assay from Article 10.1038/nchembio.2334: \\In silico design of novel probes for the atypical opioid receptor MRGPRX2.\\2017Nature chemical biology, 05, Volume: 13, Issue:5
In silico design of novel probes for the atypical opioid receptor MRGPRX2.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (354)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990229 (64.69)18.7374
1990's24 (6.78)18.2507
2000's29 (8.19)29.6817
2010's48 (13.56)24.3611
2020's24 (6.78)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 56.16

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

MetricThis Compound (vs All)
Research Demand Index56.16 (24.57)
Research Supply Index5.93 (2.92)
Research Growth Index4.62 (4.65)
Search Engine Demand Index94.94 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (56.16)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.54%)5.53%
Reviews12 (3.22%)6.00%
Case Studies5 (1.34%)4.05%
Observational1 (0.27%)0.25%
Other353 (94.64%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]