Page last updated: 2024-12-07

2-methoxy-n-n-propylnorapomorphine

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Description

2-methoxy-N-n-propylnorapomorphine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID130907
CHEMBL ID53294
SCHEMBL ID12284193
MeSH IDM0177139

Synonyms (13)

Synonym
126874-82-6
2-mnpna
2-methoxy-n-n-propylnorapomorphine
4h-dibenzo(de,g)quinoline-10,11-diol, 5,6,6a,7-tetrahydro-2-methoxy-6-propyl-, (r)-
CHEMBL53294 ,
(r)-2-methoxy-6-propyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol
2-methoxy-6-propyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol
(r)-(-)-2-methoxy-n-npropylnorapomorphine
bdbm50010692
SCHEMBL12284193
(6ar)-2-methoxy-6-propyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol
DTXSID70155319
PD178218
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
DRattus norvegicus (Norway rat)IC50 (µMol)3.32000.00030.50267.7625AID313111; AID61026
DRattus norvegicus (Norway rat)Ki3.34330.00010.610010.0000AID313111; AID317240; AID61497
D(2) dopamine receptorBos taurus (cattle)Ki0.00380.00000.58366.1000AID62464
D(1A) dopamine receptorHomo sapiens (human)Ki2.50410.00010.836310.0000AID569899; AID569900
D(3) dopamine receptorHomo sapiens (human)Ki0.00100.00000.602010.0000AID569901
D(2) dopamine receptorRattus norvegicus (Norway rat)IC50 (µMol)0.00560.00010.54948.4000AID313112; AID61403
D(2) dopamine receptorRattus norvegicus (Norway rat)Ki0.16330.00000.437510.0000AID313112; AID317241; AID569896; AID569897; AID65113
DBos taurus (cattle)Ki0.00380.00012.367610.0000AID62464
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (85)

Processvia Protein(s)Taxonomy
synaptic transmission, dopaminergicD(2) dopamine receptorBos taurus (cattle)
negative regulation of prolactin secretionD(2) dopamine receptorBos taurus (cattle)
negative regulation of lactationD(2) dopamine receptorBos taurus (cattle)
positive regulation of mammary gland involutionD(2) dopamine receptorBos taurus (cattle)
hyaloid vascular plexus regressionD(2) dopamine receptorBos taurus (cattle)
temperature homeostasisD(1A) dopamine receptorHomo sapiens (human)
conditioned taste aversionD(1A) dopamine receptorHomo sapiens (human)
behavioral fear responseD(1A) dopamine receptorHomo sapiens (human)
regulation of protein phosphorylationD(1A) dopamine receptorHomo sapiens (human)
synaptic transmission, dopaminergicD(1A) dopamine receptorHomo sapiens (human)
response to amphetamineD(1A) dopamine receptorHomo sapiens (human)
protein import into nucleusD(1A) dopamine receptorHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerD(1A) dopamine receptorHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayD(1A) dopamine receptorHomo sapiens (human)
activation of adenylate cyclase activityD(1A) dopamine receptorHomo sapiens (human)
adenylate cyclase-activating dopamine receptor signaling pathwayD(1A) dopamine receptorHomo sapiens (human)
synapse assemblyD(1A) dopamine receptorHomo sapiens (human)
memoryD(1A) dopamine receptorHomo sapiens (human)
mating behaviorD(1A) dopamine receptorHomo sapiens (human)
grooming behaviorD(1A) dopamine receptorHomo sapiens (human)
adult walking behaviorD(1A) dopamine receptorHomo sapiens (human)
visual learningD(1A) dopamine receptorHomo sapiens (human)
response to xenobiotic stimulusD(1A) dopamine receptorHomo sapiens (human)
astrocyte developmentD(1A) dopamine receptorHomo sapiens (human)
dopamine transportD(1A) dopamine receptorHomo sapiens (human)
transmission of nerve impulseD(1A) dopamine receptorHomo sapiens (human)
neuronal action potentialD(1A) dopamine receptorHomo sapiens (human)
dentate gyrus developmentD(1A) dopamine receptorHomo sapiens (human)
striatum developmentD(1A) dopamine receptorHomo sapiens (human)
cerebral cortex GABAergic interneuron migrationD(1A) dopamine receptorHomo sapiens (human)
positive regulation of cell migrationD(1A) dopamine receptorHomo sapiens (human)
peristalsisD(1A) dopamine receptorHomo sapiens (human)
operant conditioningD(1A) dopamine receptorHomo sapiens (human)
synaptic transmission, glutamatergicD(1A) dopamine receptorHomo sapiens (human)
regulation of dopamine metabolic processD(1A) dopamine receptorHomo sapiens (human)
vasodilationD(1A) dopamine receptorHomo sapiens (human)
dopamine metabolic processD(1A) dopamine receptorHomo sapiens (human)
maternal behaviorD(1A) dopamine receptorHomo sapiens (human)
positive regulation of potassium ion transportD(1A) dopamine receptorHomo sapiens (human)
glucose importD(1A) dopamine receptorHomo sapiens (human)
habituationD(1A) dopamine receptorHomo sapiens (human)
sensitizationD(1A) dopamine receptorHomo sapiens (human)
behavioral response to cocaineD(1A) dopamine receptorHomo sapiens (human)
positive regulation of release of sequestered calcium ion into cytosolD(1A) dopamine receptorHomo sapiens (human)
regulation of dopamine uptake involved in synaptic transmissionD(1A) dopamine receptorHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicD(1A) dopamine receptorHomo sapiens (human)
prepulse inhibitionD(1A) dopamine receptorHomo sapiens (human)
phospholipase C-activating dopamine receptor signaling pathwayD(1A) dopamine receptorHomo sapiens (human)
long-term synaptic potentiationD(1A) dopamine receptorHomo sapiens (human)
long-term synaptic depressionD(1A) dopamine receptorHomo sapiens (human)
cellular response to catecholamine stimulusD(1A) dopamine receptorHomo sapiens (human)
modification of postsynaptic structureD(1A) dopamine receptorHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionD(1A) dopamine receptorHomo sapiens (human)
positive regulation of neuron migrationD(1A) dopamine receptorHomo sapiens (human)
positive regulation of MAPK cascadeD(1A) dopamine receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayD(1A) dopamine receptorHomo sapiens (human)
dopamine receptor signaling pathwayD(1A) dopamine receptorHomo sapiens (human)
response to ethanolD(3) dopamine receptorHomo sapiens (human)
synaptic transmission, dopaminergicD(3) dopamine receptorHomo sapiens (human)
G protein-coupled receptor internalizationD(3) dopamine receptorHomo sapiens (human)
intracellular calcium ion homeostasisD(3) dopamine receptorHomo sapiens (human)
G protein-coupled receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
adenylate cyclase-activating dopamine receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
adenylate cyclase-inhibiting dopamine receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
learning or memoryD(3) dopamine receptorHomo sapiens (human)
learningD(3) dopamine receptorHomo sapiens (human)
locomotory behaviorD(3) dopamine receptorHomo sapiens (human)
visual learningD(3) dopamine receptorHomo sapiens (human)
response to xenobiotic stimulusD(3) dopamine receptorHomo sapiens (human)
regulation of dopamine secretionD(3) dopamine receptorHomo sapiens (human)
positive regulation of cytokinesisD(3) dopamine receptorHomo sapiens (human)
circadian regulation of gene expressionD(3) dopamine receptorHomo sapiens (human)
response to histamineD(3) dopamine receptorHomo sapiens (human)
social behaviorD(3) dopamine receptorHomo sapiens (human)
response to cocaineD(3) dopamine receptorHomo sapiens (human)
dopamine metabolic processD(3) dopamine receptorHomo sapiens (human)
response to morphineD(3) dopamine receptorHomo sapiens (human)
negative regulation of blood pressureD(3) dopamine receptorHomo sapiens (human)
positive regulation of mitotic nuclear divisionD(3) dopamine receptorHomo sapiens (human)
acid secretionD(3) dopamine receptorHomo sapiens (human)
behavioral response to cocaineD(3) dopamine receptorHomo sapiens (human)
negative regulation of oligodendrocyte differentiationD(3) dopamine receptorHomo sapiens (human)
arachidonic acid secretionD(3) dopamine receptorHomo sapiens (human)
negative regulation of protein secretionD(3) dopamine receptorHomo sapiens (human)
musculoskeletal movement, spinal reflex actionD(3) dopamine receptorHomo sapiens (human)
regulation of dopamine uptake involved in synaptic transmissionD(3) dopamine receptorHomo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionD(3) dopamine receptorHomo sapiens (human)
prepulse inhibitionD(3) dopamine receptorHomo sapiens (human)
positive regulation of dopamine receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
negative regulation of adenylate cyclase activityD(3) dopamine receptorHomo sapiens (human)
adenylate cyclase-activating adrenergic receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
negative regulation of voltage-gated calcium channel activityD(3) dopamine receptorHomo sapiens (human)
regulation of potassium ion transportD(3) dopamine receptorHomo sapiens (human)
phospholipase C-activating dopamine receptor signaling pathwayD(3) dopamine receptorHomo sapiens (human)
positive regulation of MAPK cascadeD(3) dopamine receptorHomo sapiens (human)
negative regulation of cytosolic calcium ion concentrationD(3) dopamine receptorHomo sapiens (human)
negative regulation of synaptic transmission, glutamatergicD(3) dopamine receptorHomo sapiens (human)
synaptic transmission, dopaminergicDBos taurus (cattle)
vasodilationDBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
dopamine neurotransmitter receptor activity, coupled via GsD(1A) dopamine receptorHomo sapiens (human)
G-protein alpha-subunit bindingD(1A) dopamine receptorHomo sapiens (human)
dopamine neurotransmitter receptor activityD(1A) dopamine receptorHomo sapiens (human)
protein bindingD(1A) dopamine receptorHomo sapiens (human)
heterotrimeric G-protein bindingD(1A) dopamine receptorHomo sapiens (human)
dopamine bindingD(1A) dopamine receptorHomo sapiens (human)
arrestin family protein bindingD(1A) dopamine receptorHomo sapiens (human)
G protein-coupled receptor activityD(1A) dopamine receptorHomo sapiens (human)
dopamine neurotransmitter receptor activity, coupled via Gi/GoD(3) dopamine receptorHomo sapiens (human)
protein bindingD(3) dopamine receptorHomo sapiens (human)
G protein-coupled receptor activityD(3) dopamine receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
Golgi membraneD(2) dopamine receptorBos taurus (cattle)
nucleusD(1A) dopamine receptorHomo sapiens (human)
endoplasmic reticulum membraneD(1A) dopamine receptorHomo sapiens (human)
plasma membraneD(1A) dopamine receptorHomo sapiens (human)
ciliumD(1A) dopamine receptorHomo sapiens (human)
presynaptic membraneD(1A) dopamine receptorHomo sapiens (human)
dendritic spineD(1A) dopamine receptorHomo sapiens (human)
postsynaptic membraneD(1A) dopamine receptorHomo sapiens (human)
ciliary membraneD(1A) dopamine receptorHomo sapiens (human)
non-motile ciliumD(1A) dopamine receptorHomo sapiens (human)
glutamatergic synapseD(1A) dopamine receptorHomo sapiens (human)
GABA-ergic synapseD(1A) dopamine receptorHomo sapiens (human)
G protein-coupled receptor complexD(1A) dopamine receptorHomo sapiens (human)
plasma membraneD(1A) dopamine receptorHomo sapiens (human)
plasma membraneD(3) dopamine receptorHomo sapiens (human)
synapseD(3) dopamine receptorHomo sapiens (human)
plasma membraneD(3) dopamine receptorHomo sapiens (human)
endoplasmic reticulum membraneDBos taurus (cattle)
dendritic spineDBos taurus (cattle)
ciliary membraneDBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID313111Displacement of [3H]SCH-23390 from rat dopamine D1 receptor2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Advances in development of dopaminergic aporphinoids.
AID569899Binding affinity to dopamine D1 receptor low binding site by radioligand displacement assay2011ACS medicinal chemistry letters, Mar-10, Volume: 2, Issue:3
Synthesis and Evaluation of Fluorinated Aporphines: Potential Positron Emission Tomography Ligands for D2 Receptors
AID226917Ratio of binding affinity of D2 to binding affinity of D11990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues.
AID317241Displacement of [3H]neomonapride from dopamine D2 receptor in rat striatum2008Journal of medicinal chemistry, Feb-28, Volume: 51, Issue:4
Synthesis and dopamine receptor affinities of N-alkyl-11-hydroxy-2-methoxynoraporphines: N-alkyl substituents determine D1 versus D2 receptor selectivity.
AID317240Displacement of [3H]SCH-23390 from dopamine D1 receptor in rat striatum2008Journal of medicinal chemistry, Feb-28, Volume: 51, Issue:4
Synthesis and dopamine receptor affinities of N-alkyl-11-hydroxy-2-methoxynoraporphines: N-alkyl substituents determine D1 versus D2 receptor selectivity.
AID65113Binding affinity at rat striatal Dopamine receptor D2 using [3H]- piperone radioligand1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues.
AID61403Binding affinity against Dopamine receptor D2 from rat brain corpus striatum membrane1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Synthesis and dopamine receptor affinity of (R)-(-)-2-fluoro-N-n-propylnorapomorphine: a highly potent and selective dopamine D2 agonist.
AID317242Selectivity ratio of rat dopamine D2 receptor to rat dopamine D1 receptor2008Journal of medicinal chemistry, Feb-28, Volume: 51, Issue:4
Synthesis and dopamine receptor affinities of N-alkyl-11-hydroxy-2-methoxynoraporphines: N-alkyl substituents determine D1 versus D2 receptor selectivity.
AID313112Displacement of [3H]raclopride from rat dopamine D2 receptor2007Journal of medicinal chemistry, Jan-25, Volume: 50, Issue:2
Advances in development of dopaminergic aporphinoids.
AID569896Displacement of [3H]SCH23390 from dopamine D2 receptor low binding site in Sprague-Dawley rat striatum by scintillation counting2011ACS medicinal chemistry letters, Mar-10, Volume: 2, Issue:3
Synthesis and Evaluation of Fluorinated Aporphines: Potential Positron Emission Tomography Ligands for D2 Receptors
AID569900Binding affinity to dopamine D1 receptor high binding site by radioligand displacement assay2011ACS medicinal chemistry letters, Mar-10, Volume: 2, Issue:3
Synthesis and Evaluation of Fluorinated Aporphines: Potential Positron Emission Tomography Ligands for D2 Receptors
AID569901Displacement of [3H]domperidone from human dopamine D3 receptor expressed in human HEK293 cells by scintillation counting2011ACS medicinal chemistry letters, Mar-10, Volume: 2, Issue:3
Synthesis and Evaluation of Fluorinated Aporphines: Potential Positron Emission Tomography Ligands for D2 Receptors
AID62464Agonistic activity against calf striatal Dopamine receptor using [3H]- ADTN radioligand1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues.
AID226901Potency ratio as ratio of IC50 of D2 receptor to that of D1 receptor1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Synthesis and dopamine receptor affinity of (R)-(-)-2-fluoro-N-n-propylnorapomorphine: a highly potent and selective dopamine D2 agonist.
AID61026Binding affinity against Dopamine receptor D1 from rat brain corpus striatum membrane1990Journal of medicinal chemistry, Dec, Volume: 33, Issue:12
Synthesis and dopamine receptor affinity of (R)-(-)-2-fluoro-N-n-propylnorapomorphine: a highly potent and selective dopamine D2 agonist.
AID61497Binding affinity at rat striatal Dopamine receptor D1 using [3H]- SCH-23390 radioligand1990Journal of medicinal chemistry, Jun, Volume: 33, Issue:6
Synthesis and dopamine receptor affinities of enantiomers of 2-substituted apomorphines and their N-n-propyl analogues.
AID569897Displacement of [3H]domperidone from dopamine D2 receptor high binding site in Sprague-Dawley rat striatum by scintillation counting2011ACS medicinal chemistry letters, Mar-10, Volume: 2, Issue:3
Synthesis and Evaluation of Fluorinated Aporphines: Potential Positron Emission Tomography Ligands for D2 Receptors
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (25.00)18.2507
2000's5 (62.50)29.6817
2010's1 (12.50)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: 12.36

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 Index12.36 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.56 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.36)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (12.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (87.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]