Page last updated: 2024-12-08

1-isoamyl-3-isobutylxanthine

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

1-isoamyl-3-isobutylxanthine (also known as **IBMX**) is a **phosphodiesterase inhibitor**.

**What does that mean?**

* **Phosphodiesterases (PDEs)** are enzymes that break down cyclic nucleotides, like cyclic AMP (cAMP) and cyclic GMP (cGMP).
* **cAMP and cGMP** are important second messengers in cellular signaling pathways. They activate various downstream proteins involved in diverse processes like:
* Cell growth and division
* Muscle contraction
* Hormone secretion
* Immune response
* Memory and learning

**IBMX inhibits PDEs, preventing them from breaking down cAMP and cGMP.** This leads to an increase in the intracellular levels of these messengers, amplifying their signaling effects.

**Why is IBMX important for research?**

IBMX is a valuable tool in research for several reasons:

* **Investigating cAMP/cGMP signaling:** By blocking PDE activity, IBMX allows researchers to study the effects of increased cAMP/cGMP levels in various cellular processes.
* **Understanding PDE function:** IBMX can be used to identify different PDE subtypes and their specific roles in different tissues and cells.
* **Drug discovery:** IBMX serves as a lead compound for developing new drugs that target PDEs, potentially treating various diseases.
* **Experimental models:** IBMX is often used in experimental models to mimic the effects of certain diseases or conditions that involve altered cAMP/cGMP signaling.

**Examples of research applications:**

* **Studying the role of cAMP in memory formation:** IBMX can enhance memory in animal models by increasing cAMP levels in the brain.
* **Investigating the effects of PDE inhibitors on heart function:** IBMX can be used to study the potential benefits of PDE inhibitors in treating heart failure.
* **Developing new drugs for treating asthma:** Some PDE inhibitors, including IBMX derivatives, are being investigated as potential treatments for asthma by relaxing airway smooth muscle.

**It's important to note that IBMX is a research tool and not a medication for human use. It has potential side effects, and its use should be carefully controlled under laboratory conditions.**

Cross-References

ID SourceID
PubMed CID152034
CHEMBL ID20613
SCHEMBL ID10579248
MeSH IDM0081940

Synonyms (13)

Synonym
1-isoamyl-3-isobutylxanthine
CHEMBL20613 ,
3-isobutyl-1-(3-methyl-butyl)-3,7-dihydro-purine-2,6-dione
bdbm50018154
3-isobutyl-1-isoamylxanthine
1h-purine-2,6-dione, 3,7-dihydro-1-(3-methylbutyl)-3-(2-methylpropyl)-
63908-26-9
unii-976sw405sb
976sw405sb ,
1h-purine-2,6-dione, 3,9-dihydro-1-(3-methylbutyl)-3-(2-methylpropyl)-
SCHEMBL10579248
DTXSID30213606
Q27271973
[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)
Adenosine receptor A1Rattus norvegicus (Norway rat)Ki7.30000.00011.20929.9700AID31856; AID32491
Adenosine receptor A2aHomo sapiens (human)Ki6.50000.00001.06099.7920AID30797
Adenosine receptor A2bHomo sapiens (human)Ki6.37000.00021.635210.0000AID30797; AID33176
Adenosine receptor A2bRattus norvegicus (Norway rat)Ki6.50000.00061.353610.0000AID30797
Adenosine receptor A2aRattus norvegicus (Norway rat)Ki6.50000.00021.494010.0000AID30797
Adenosine receptor A2aCavia porcellus (domestic guinea pig)Ki150.00000.11002.63858.0000AID30621
[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 (10)

Assay IDTitleYearJournalArticle
AID158581Inhibition of Calmodulin Sensitive Phosphodiesterase 1 from pig coronary artery1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Inhibition of cyclic nucleotide phosphodiesterases from pig coronary artery by benzo-separated analogues of 3-isobutyl-1-methylxanthine.
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.
AID229822Ratio of antagonism at A2 versus A1 receptors (Ki values)1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.
AID30807Binding affinity against Adenosine A2 receptor in rat striatal membranes using [3H]5'-(N-ethylcarboxamido)-adenosine (NECA) as the ligand1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Synthesis of paraxanthine analogs (1,7-disubstituted xanthines) and other xanthines unsubstituted at the 3-position: structure-activity relationships at adenosine receptors.
AID31856Antagonism of binding of 1 nM [3H]cyclohexyladenosine to adenosine A1 receptors on rat cortical membranes1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.
AID31881Binding affinity at Adenosine A1 receptor in rat brain cortical membrane using [3H]N6-R-phenylisopropyladenosine (R-PIA) as radioligand1993Journal of medicinal chemistry, Oct-29, Volume: 36, Issue:22
Synthesis of paraxanthine analogs (1,7-disubstituted xanthines) and other xanthines unsubstituted at the 3-position: structure-activity relationships at adenosine receptors.
AID30621Antagonism of cyclic [3H]AMP accumulation in guinea pig cerebral cortical slices (elicited by 15 uM 2-chloroadenosine at adenosine A2 receptor)1985Journal of medicinal chemistry, Apr, Volume: 28, Issue:4
1,3-Dialkyl-8-(p-sulfophenyl)xanthines: potent water-soluble antagonists for A1- and A2-adenosine receptors.
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.
AID33176Binding affinity at human Adenosine A2B receptor expressed in HEK293 cells, using [125I]ABOPX as radioligand2002Journal of medicinal chemistry, May-23, Volume: 45, Issue:11
Structure-activity relationships at human and rat A2B adenosine receptors of xanthine derivatives substituted at the 1-, 3-, 7-, and 8-positions.
AID158582Inhibition of Phosphodiesterase 2 from pig coronary artery1986Journal of medicinal chemistry, Jun, Volume: 29, Issue:6
Inhibition of cyclic nucleotide phosphodiesterases from pig coronary artery by benzo-separated analogues of 3-isobutyl-1-methylxanthine.
[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-19906 (75.00)18.7374
1990's1 (12.50)18.2507
2000's1 (12.50)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: 11.98

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 Index11.98 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.18 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.98)

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]