Page last updated: 2024-11-12

a-796260

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Description

(1-(2-morpholin-4-yl-ethyl)-1H-indol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11584525
CHEMBL ID262865
SCHEMBL ID2076954
MeSH IDM0519816

Synonyms (25)

Synonym
bdbm21311
chembl262865 ,
4-(2-{3-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-1h-indol-1-yl}ethyl)morpholine
[1-(2-morpholin-4-ylethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone
a-796260
895155-26-7
a796260
5n69dxa53z ,
a 796260
(1-(2-morpholin-4-yl-ethyl)-1h-indol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone
unii-5n69dxa53z
(1-(2-morpholinoethyl)-1h-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone
AKOS015999103
a-796,260
a796,260
methanone, (1-(2-(4-morpholinyl)ethyl)-1h-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)-
SCHEMBL2076954
ZCFHOMLAFTWDFM-UHFFFAOYSA-N ,
mfcd22421643
[1-[2-(4-morpholinyl)ethyl]-1h-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone
Q4646876
AS-19178
DTXSID801010107
[1-[2-(4-morpholinyl)ethyl]-1h-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)-methanone
[1-(2-morpholin-4-ylethyl)-1h-indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 1Homo sapiens (human)IC50 (µMol)0.33000.00010.275310.0000AID323714; AID412565
Cannabinoid receptor 1Homo sapiens (human)Ki0.75580.00010.50779.6000AID1798067; AID324969; AID444910; AID569312
Cannabinoid receptor 2 Homo sapiens (human)IC50 (µMol)0.00080.00081.58409.8000AID323715; AID412566
Cannabinoid receptor 2 Homo sapiens (human)Ki0.10950.00000.415610.0000AID1798067; AID324968; AID444909; AID569313; AID620816
[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)
Cannabinoid receptor 1Rattus norvegicus (Norway rat)EC50 (µMol)0.24800.00020.19211.9953AID444918
Cannabinoid receptor 1Homo sapiens (human)EC50 (µMol)0.81100.00010.12752.2400AID444914
Cannabinoid receptor 2 Homo sapiens (human)EC50 (µMol)0.01020.00030.15173.2800AID324971; AID444912; AID444916
Cannabinoid receptor 2Rattus norvegicus (Norway rat)EC50 (µMol)0.00160.00030.06660.3150AID444920
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
positive regulation of acute inflammatory response to antigenic stimulusCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
spermatogenesisCannabinoid receptor 1Homo sapiens (human)
axonal fasciculationCannabinoid receptor 1Homo sapiens (human)
response to nutrientCannabinoid receptor 1Homo sapiens (human)
memoryCannabinoid receptor 1Homo sapiens (human)
positive regulation of neuron projection developmentCannabinoid receptor 1Homo sapiens (human)
negative regulation of serotonin secretionCannabinoid receptor 1Homo sapiens (human)
positive regulation of fever generationCannabinoid receptor 1Homo sapiens (human)
negative regulation of fatty acid beta-oxidationCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, GABAergicCannabinoid receptor 1Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 1Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 1Homo sapiens (human)
negative regulation of dopamine secretionCannabinoid receptor 1Homo sapiens (human)
response to nicotineCannabinoid receptor 1Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 1Homo sapiens (human)
response to cocaineCannabinoid receptor 1Homo sapiens (human)
glucose homeostasisCannabinoid receptor 1Homo sapiens (human)
positive regulation of apoptotic processCannabinoid receptor 1Homo sapiens (human)
response to ethanolCannabinoid receptor 1Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 1Homo sapiens (human)
negative regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
positive regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
regulation of insulin secretionCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicCannabinoid receptor 1Homo sapiens (human)
maternal process involved in female pregnancyCannabinoid receptor 1Homo sapiens (human)
regulation of feeding behaviorCannabinoid receptor 1Homo sapiens (human)
regulation of penile erectionCannabinoid receptor 1Homo sapiens (human)
retrograde trans-synaptic signaling by endocannabinoidCannabinoid receptor 1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationCannabinoid receptor 1Homo sapiens (human)
trans-synaptic signaling by endocannabinoid, modulating synaptic transmissionCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 1Homo sapiens (human)
response to amphetamineCannabinoid receptor 2 Homo sapiens (human)
inflammatory responseCannabinoid receptor 2 Homo sapiens (human)
immune responseCannabinoid receptor 2 Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 2 Homo sapiens (human)
leukocyte chemotaxisCannabinoid receptor 2 Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicCannabinoid receptor 2 Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 2 Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 2 Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 2 Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 2 Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
cannabinoid receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 1Homo sapiens (human)
identical protein bindingCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 2 Homo sapiens (human)
cannabinoid receptor activityCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
mitochondrial outer membraneCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
actin cytoskeletonCannabinoid receptor 1Homo sapiens (human)
growth coneCannabinoid receptor 1Homo sapiens (human)
presynaptic membraneCannabinoid receptor 1Homo sapiens (human)
membrane raftCannabinoid receptor 1Homo sapiens (human)
glutamatergic synapseCannabinoid receptor 1Homo sapiens (human)
GABA-ergic synapseCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
cytoplasmCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
dendriteCannabinoid receptor 2 Homo sapiens (human)
extrinsic component of cytoplasmic side of plasma membraneCannabinoid receptor 2 Homo sapiens (human)
perikaryonCannabinoid receptor 2 Homo sapiens (human)
endoplasmic reticulumCannabinoid receptor 2 Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
cytoplasmCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID444916Agonist activity at human recombinant CB2 receptor expressed in HEK293 cells assessed as inhibition of forskolin-induced cAMP production2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID620816Displacement of [3H]-WIN 55,212-2 from human CB2 receptor expressed in human HEK293 cells after 90 mins by radioligand assay2011European journal of medicinal chemistry, Sep, Volume: 46, Issue:9
Homology modeling in tandem with 3D-QSAR analyses: a computational approach to depict the agonist binding site of the human CB2 receptor.
AID444914Agonist activity at human recombinant CB1 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP production2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID444918Agonist activity at rat CB1 receptor assessed as inhibition of forskolin-induced cAMP production by cell based assay2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID444912Agonist activity at human recombinant CB2 receptor expressed in HEK293 cells coexpressing Galphaq/o5 assessed as calcium mobilization by FLIPR assay2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID324973Antiinflammatory activity against rat CFA-induced chronic inflammatory thermal hyperalgesia model assessed as effect on paw withdrawal latency2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity.
AID444910Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in CHO cells2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID444911Selectivity ratio of Ki for human recombinant CB1 receptor to Ki for human recombinant CB2 receptor2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID444909Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HEK293 cells2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID569312Displacement of [3H]CP 55940 from human CB1 receptor in cell free system2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Three-dimensional quantitative structure-selectivity relationships analysis guided rational design of a highly selective ligand for the cannabinoid receptor 2.
AID324969Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HEK cells2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity.
AID323715Binding affinity to CB2 receptor2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Imine derivatives as new potent and selective CB2 cannabinoid receptor agonists with an analgesic action.
AID444913Agonist activity at human recombinant CB2 receptor expressed in HEK293 cells coexpressing Galphaq/o5 assessed as calcium mobilization by FLIPR assay relative to CP-559402010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID569313Displacement of [3H]CP 55940 from human CB2 receptor in cell free system2011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Three-dimensional quantitative structure-selectivity relationships analysis guided rational design of a highly selective ligand for the cannabinoid receptor 2.
AID444920Agonist activity at rat CB2 receptor assessed as inhibition of forskolin-induced cAMP production by cell based assay2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID324968Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HEK cells2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity.
AID412567Selectivity ratio of Ki for human CB1 receptor to Ki for human CB2 receptor2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Discovery of novel CB2 receptor ligands by a pharmacophore-based virtual screening workflow.
AID324970Selectivity for human recombinant CB2 receptor over human recombinant CB1 receptor2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity.
AID412565Displacement of [3H]CP-55940 from human recombinant CB1 receptor2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Discovery of novel CB2 receptor ligands by a pharmacophore-based virtual screening workflow.
AID444919Agonist activity at rat CB1 receptor assessed as inhibition of forskolin-induced cAMP production by cell based assay relative to CP-559402010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID324971Agonist activity at human recombinant CB2 receptor expressed in HEK cells assessed as calcium mobilization by FLIPR2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity.
AID412566Displacement of [3H]CP-55940 from human recombinant CB2 receptor2009Journal of medicinal chemistry, Jan-22, Volume: 52, Issue:2
Discovery of novel CB2 receptor ligands by a pharmacophore-based virtual screening workflow.
AID323714Binding affinity to CB1 receptor2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Imine derivatives as new potent and selective CB2 cannabinoid receptor agonists with an analgesic action.
AID569314Selectivity ratio of Ki for human CB1 to Ki for human CB22011European journal of medicinal chemistry, Feb, Volume: 46, Issue:2
Three-dimensional quantitative structure-selectivity relationships analysis guided rational design of a highly selective ligand for the cannabinoid receptor 2.
AID324972Agonist activity at human recombinant CB2 receptor expressed in HEK cells assessed as calcium mobilization by FLIPR relative to CP-559402008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity.
AID444922Selectivity ratio of EC50 for human recombinant CB1 receptor to EC50 for human recombinant CB2 receptor2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID444915Agonist activity at human recombinant CB1 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP production relative to CP-559402010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID444917Agonist activity at human recombinant CB2 receptor expressed in HEK293 cells assessed as inhibition of forskolin-induced cAMP production relative to CP-559402010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID444921Agonist activity at rat CB2 receptor assessed as inhibition of forskolin-induced cAMP production by cell based assay relative to CP-559402010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID444923Selectivity ratio of EC50 for rat CB1 receptor to EC50 for rat CB2 receptor2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity.
AID1798067Radioligand Binding Assay from Article 10.1021/jm7011613: \\Indol-3-yl-tetramethylcyclopropyl Ketones: Effects of Indole Ring Substitution on CB2 Cannabinoid Receptor Activity.\\2008Journal of medicinal chemistry, Mar-27, Volume: 51, Issue:6
Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity.
[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's0 (0.00)18.2507
2000's4 (50.00)29.6817
2010's3 (37.50)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.51

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

MetricThis Compound (vs All)
Research Demand Index17.51 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.52 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.51)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]