Page last updated: 2024-11-08

8-cyclohexylcaffeine

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

Cross-References

ID SourceID
PubMed CID225229
CHEMBL ID281811
SCHEMBL ID5935691
MeSH IDM0279356

Synonyms (9)

Synonym
8-cyclohexyl-1,3,7-trimethylpurine-2,6-dione
nsc14389
nsc-14389
CHEMBL281811 ,
8-cyclohexyl-1,3,7-trimethyl-3,7-dihydro-purine-2,6-dione
bdbm50008416
SCHEMBL5935691
1,3,7-trimethyl-8-cyclohexylxanthine
8-cyclohexylcaffeine
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki10.00070.00011.20929.9700AID32178; AID32487; AID32491
Adenosine receptor A2aHomo sapiens (human)Ki1.43010.00001.06099.7920AID30655; AID30797; AID33734
Adenosine receptor A2bHomo sapiens (human)Ki1.43010.00021.635210.0000AID30655; AID30797; AID33734
Adenosine receptor A2bRattus norvegicus (Norway rat)Ki2.14500.00061.353610.0000AID30797; AID33734
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki2.14500.00021.494010.0000AID30797; AID33734
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (61)

Processvia Protein(s)Taxonomy
synaptic transmission, dopaminergicAdenosine receptor A2aHomo sapiens (human)
response to amphetamineAdenosine receptor A2aHomo sapiens (human)
regulation of DNA-templated transcriptionAdenosine receptor A2aHomo sapiens (human)
phagocytosisAdenosine receptor A2aHomo sapiens (human)
apoptotic processAdenosine receptor A2aHomo sapiens (human)
inflammatory responseAdenosine receptor A2aHomo sapiens (human)
cellular defense responseAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
protein kinase C-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
cell-cell signalingAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, cholinergicAdenosine receptor A2aHomo sapiens (human)
central nervous system developmentAdenosine receptor A2aHomo sapiens (human)
blood coagulationAdenosine receptor A2aHomo sapiens (human)
sensory perceptionAdenosine receptor A2aHomo sapiens (human)
locomotory behaviorAdenosine receptor A2aHomo sapiens (human)
blood circulationAdenosine receptor A2aHomo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A2aHomo sapiens (human)
response to xenobiotic stimulusAdenosine receptor A2aHomo sapiens (human)
response to inorganic substanceAdenosine receptor A2aHomo sapiens (human)
positive regulation of glutamate secretionAdenosine receptor A2aHomo sapiens (human)
positive regulation of acetylcholine secretion, neurotransmissionAdenosine receptor A2aHomo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A2aHomo sapiens (human)
response to purine-containing compoundAdenosine receptor A2aHomo sapiens (human)
response to caffeineAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, GABAergicAdenosine receptor A2aHomo sapiens (human)
synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
positive regulation of urine volumeAdenosine receptor A2aHomo sapiens (human)
vasodilationAdenosine receptor A2aHomo sapiens (human)
eating behaviorAdenosine receptor A2aHomo sapiens (human)
negative regulation of vascular permeabilityAdenosine receptor A2aHomo sapiens (human)
negative regulation of neuron apoptotic processAdenosine receptor A2aHomo sapiens (human)
positive regulation of circadian sleep/wake cycle, sleepAdenosine receptor A2aHomo sapiens (human)
negative regulation of alpha-beta T cell activationAdenosine receptor A2aHomo sapiens (human)
astrocyte activationAdenosine receptor A2aHomo sapiens (human)
neuron projection morphogenesisAdenosine receptor A2aHomo sapiens (human)
positive regulation of protein secretionAdenosine receptor A2aHomo sapiens (human)
negative regulation of inflammatory responseAdenosine receptor A2aHomo sapiens (human)
regulation of mitochondrial membrane potentialAdenosine receptor A2aHomo sapiens (human)
membrane depolarizationAdenosine receptor A2aHomo sapiens (human)
regulation of calcium ion transportAdenosine receptor A2aHomo sapiens (human)
positive regulation of synaptic transmission, glutamatergicAdenosine receptor A2aHomo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
inhibitory postsynaptic potentialAdenosine receptor A2aHomo sapiens (human)
prepulse inhibitionAdenosine receptor A2aHomo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2aHomo sapiens (human)
positive regulation of long-term synaptic potentiationAdenosine receptor A2aHomo sapiens (human)
positive regulation of apoptotic signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
positive regulation of chronic inflammatory response to non-antigenic stimulusAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A2bHomo sapiens (human)
positive regulation of vascular endothelial growth factor productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
cGMP-mediated signalingAdenosine receptor A2bHomo sapiens (human)
positive regulation of chemokine productionAdenosine receptor A2bHomo sapiens (human)
positive regulation of interleukin-6 productionAdenosine receptor A2bHomo sapiens (human)
mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
positive regulation of mast cell degranulationAdenosine receptor A2bHomo sapiens (human)
relaxation of vascular associated smooth muscleAdenosine receptor A2bHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A2bHomo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayAdenosine receptor A2bHomo sapiens (human)
vasodilationAdenosine receptor A2bHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A2aHomo sapiens (human)
protein bindingAdenosine receptor A2aHomo sapiens (human)
calmodulin bindingAdenosine receptor A2aHomo sapiens (human)
lipid bindingAdenosine receptor A2aHomo sapiens (human)
enzyme bindingAdenosine receptor A2aHomo sapiens (human)
type 5 metabotropic glutamate receptor bindingAdenosine receptor A2aHomo sapiens (human)
identical protein bindingAdenosine receptor A2aHomo sapiens (human)
protein-containing complex bindingAdenosine receptor A2aHomo sapiens (human)
alpha-actinin bindingAdenosine receptor A2aHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2bHomo sapiens (human)
protein bindingAdenosine receptor A2bHomo sapiens (human)
G protein-coupled receptor activityAdenosine receptor A2bHomo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A2aHomo sapiens (human)
intermediate filamentAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2aHomo sapiens (human)
membraneAdenosine receptor A2aHomo sapiens (human)
dendriteAdenosine receptor A2aHomo sapiens (human)
axolemmaAdenosine receptor A2aHomo sapiens (human)
asymmetric synapseAdenosine receptor A2aHomo sapiens (human)
presynaptic membraneAdenosine receptor A2aHomo sapiens (human)
neuronal cell bodyAdenosine receptor A2aHomo sapiens (human)
postsynaptic membraneAdenosine receptor A2aHomo sapiens (human)
presynaptic active zoneAdenosine receptor A2aHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2aHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A2bHomo sapiens (human)
presynapseAdenosine receptor A2bHomo sapiens (human)
glutamatergic synapseAdenosine receptor A2bHomo sapiens (human)
plasma membraneAdenosine receptor A2bHomo sapiens (human)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID32487Inhibition of 1 nM [3H]- N6 -(phenylisopropyl) adenosine binding to Adenosine A1 receptor in rat fat cell membrane1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.
AID30797Inhibition of the stimulation by 5'-(N-ethylcarbamoyl) adenosine of adenyl cyclase via adenosine A2 receptor in human platelet membranes.1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.
AID32178Binding affinity for adenosine A1 receptor using [3H]- CHA or [3H]- PIA antagonism of adenylate cyclase inhibition in rat adipocytes1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.
AID35014Ability to inhibit binding of [3H]NECA to Adenosine A2A receptor in rat brain striatal membranes1997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
Synthesis and structure-activity relationships of 3,7-dimethyl-1-propargylxanthine derivatives, A2A-selective adenosine receptor antagonists.
AID31710Ability to inhibit binding of [3H]R-PIA to Adenosine A1 receptor in rat brain cortical membranes1997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
Synthesis and structure-activity relationships of 3,7-dimethyl-1-propargylxanthine derivatives, A2A-selective adenosine receptor antagonists.
AID30655Binding affinity for adenosine A2 receptor using [3H]- NECA antagonism of adenylate cyclase activation in human platelets1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.
AID32327Affinity against Adenosine A1 receptor in rat brain using [3H]- PIA as radioligand1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Structure-activity relationships of 8-styrylxanthines as A2-selective adenosine antagonists.
AID33594Binding affinity against adenosine A2 receptor in rat brain using [3H]- CGS 21680 as radioligand1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Structure-activity relationships of 8-styrylxanthines as A2-selective adenosine antagonists.
AID32491Inhibition of 1 nM [3H]- N6-(phenylisopropyl) adenosine binding to Adenosine A1 receptor in rat cerebral cortical membranes1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.
AID33752Ratio of A2 to A1.1992Journal of medicinal chemistry, Feb-07, Volume: 35, Issue:3
Adenosine receptors: pharmacology, structure-activity relationships, and therapeutic potential.
AID231678Ratio between Ki of adenosine A1 receptor to that of adenosine A2 receptor1993Journal of medicinal chemistry, May-14, Volume: 36, Issue:10
Structure-activity relationships of 8-styrylxanthines as A2-selective adenosine antagonists.
AID33734Inhibition of the stimulation by 5'-(N-ethylcarbamoyl) adenosine of adenyl cyclase via Adenosine A2 receptor in rat PC12 membranes1989Journal of medicinal chemistry, Jun, Volume: 32, Issue:6
Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.
AID233916Selectivity ratio as adenosine A1 receptor/adenosine A2A receptor.1997Journal of medicinal chemistry, Dec-19, Volume: 40, Issue:26
Synthesis and structure-activity relationships of 3,7-dimethyl-1-propargylxanthine derivatives, A2A-selective adenosine receptor antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (20.00)18.7374
1990's4 (80.00)18.2507
2000's0 (0.00)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: 13.09

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 Index13.09 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.88 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.09)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (20.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other4 (80.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]