ISOBUTYLMETHYLXANTHINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H14N4O2
Molecular Weight	222.2438
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)CN1C2=C(N=CN2)C(=O)N(C)C1=O

InChI

InChIKey=APIXJSLKIYYUKG-UHFFFAOYSA-N

InChI=1S/C10H14N4O2/c1-6(2)4-14-8-7(11-5-12-8)9(15)13(3)10(14)16/h5-6H,4H2,1-3H3,(H,11,12)

HIDE SMILES / InChI

Molecular Formula	C10H14N4O2
Molecular Weight	222.2438
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Potency
Phosphodiesterase 1 12 Target ID: CHEMBL2097166 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8504	19.0 µM [IC50]
Phosphodiesterase 2A 7 Target ID: CHEMBL3477 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8504	50.0 µM [IC50]
Phosphodiesterase 3B 8 Target ID: CHEMBL5129 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8504	18.0 µM [IC50]
Phosphodiesterase 4 54 Target ID: CHEMBL2093863 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8504	13.0 µM [IC50]
Phosphodiesterase 5A 31 Target ID: CHEMBL3478 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1665737 \| https://www.ncbi.nlm.nih.gov/pubmed/8003849	Inhibitor 8504	32.0 µM [IC50]

PubMed

Title	Date	PubMed
Cystic fibrosis transmembrane regulator regulates uptake of sphingoid base phosphates and lysophosphatidic acid: modulation of cellular activity of sphingosine 1-phosphate.	2001-09-21	11443135
Structure-activity and possible mode of action of S-Iamide neuropeptides on identified central neurons of Helix aspersa.	2001-09-15	11495688
Persistent corticotropin-releasing factor(1) receptor desensitization and downregulation in the human neuroblastoma cell line IMR-32.	2001-08-15	11483248
Mechanism for muscarinic inhibition of I(Ca(L)) is determined by the path for elevating cyclic AMP in cardiac myocytes.	2001-08-01	11470473
Cytokine induction of Fas gene expression in insulin-producing cells requires the transcription factors NF-kappaB and C/EBP.	2001-08	11473033
Platelet-derived growth factor stimulates phospholipase C-gamma 1, extracellular signal-regulated kinase, and arachidonic acid release in rat myometrial cells: contribution to cyclic 3',5'-adenosine monophosphate production and effect on cell proliferation.	2001-08	11466218
Members of the Kv1 and Kv2 voltage-dependent K(+) channel families regulate insulin secretion.	2001-08	11463864
Regulation of cAMP by light and dopamine receptors is dysfunctional in photoreceptors of dystrophic retinal degeneration slow(rds) mice.	2001-08	11446777
Long-term hormonal regulation of the cAMP-specific phosphodiesterases in cultured FRTL-5 thyroid cells.	2001-07-25	11476896
[Cyclonucleotide-dependent pathway--one of the mechanisms of olfactory transduction of the amino acid signal in Cyprinus carpio].	2001-07-17	11452779
8-chloro-cAMP and 8-chloro-adenosine act by the same mechanism in multiple myeloma cells.	2001-07-15	11454694
cAMP protection of pancreatic cancer cells against apoptosis induced by ERK inhibition.	2001-07-13	11444827
Biphasic response to human galanin of extracellular acidification in human Bowes melanoma cells.	2001-07-06	11448477
Effect of somatostatin on cholecystokinin-induced amylase release in rat pancreatic acini.	2001-07	11451139
Riboflavin uptake in human trophoblast-derived BeWo cell monolayers: cellular translocation and regulatory mechanisms.	2001-07	11408551
ClC-2 Cl- channels in human lung epithelia: activation by arachidonic acid, amidation, and acid-activated omeprazole.	2001-07	11401826
Insulin-stimulated hydrogen peroxide reversibly inhibits protein-tyrosine phosphatase 1b in vivo and enhances the early insulin action cascade.	2001-06-15	11297536
Assessment of DNA damage in C6 glioma cells after antidepressant treatment using an alkaline comet assay.	2001-06	11482523
Prostaglandins and nitric oxide mediate superoxide-induced myocardial contractile dysfunction in isolated rat hearts.	2001-06	11444916
Expression and function of brain-derived neurotrophin factor and its receptor, TrkB, in ovarian follicles from the domestic hen (Gallus gallus domesticus).	2001-06	11441050
N-acetylneuraminic acid (NANA) stimulates in situ cyclic AMP production in tentacles of sea anemone (Aiptasia pallida): possible role in chemosensitization of nematocyst discharge.	2001-06	11441042
Role of cyclic nucleotide phosphodiesterase isoenzymes in contractile responses of denuded rat aorta related to various Ca2+ sources.	2001-06	11414656
Selective inhibition of beta(2)-adrenergic receptor-mediated cAMP generation by activation of the P2Y(2) receptor in mouse pineal gland tumor cells.	2001-06	11413231
Synergism between nitric oxide and hydrogen peroxide in the inhibition of platelet function: the roles of soluble guanylyl cyclase and vasodilator-stimulated phosphoprotein.	2001-06	11384196
Spontaneous and receptor-controlled soluble guanylyl cyclase activity in anterior pituitary cells.	2001-06	11376118
cAMP and excitability in neuroendocrine cells during reproductive senescence.	2001-05-30	11378258
The role of cGMP hydrolysing phosphodiesterases 1 and 5 in cerebral artery dilatation.	2001-05-18	11412839
Functional consequences of the arrhythmogenic G306R KvLQT1 K+ channel mutant probed by viral gene transfer in cardiomyocytes.	2001-05-15	11351021
Gap junction-dependent increases in smooth muscle cAMP underpin the EDHF phenomenon in rabbit arteries.	2001-05-11	11341764
The influence of cAMP before or during bovine oocyte maturation on embryonic developmental competence.	2001-05-01	11393223
The role of cyclic AMP in the pathogenesis of glucose desensitization in rat pancreatic islets.	2001-05	11345144
The Drosophila melanogaster homologue of an insect calcitonin-like diuretic peptide stimulates V-ATPase activity in fruit fly Malpighian tubules.	2001-05	11316500
Sonic hedgehog and FGF8: inadequate signals for the differentiation of a dopamine phenotype in mouse and human neurons in culture.	2001-05	11312556
Effects of cyclic adenosine-monophosphate on growth and PSA secretion of human prostate cancer cell line.	2001-05	11295058
Rhythmicity of the cGMP-related signal transduction pathway in the mammalian circadian system.	2001-05	11294753
The expression and regulation of depolarization-activated K+ channels in the insulin-secreting cell line INS-1.	2001-04	11374068
Inhibition of rat cardiac fibroblast growth by cAMP--but not by cGMP-dependent protein kinase.	2001-04	11327337
Evaluation of signal transduction pathways in chemoattractant-induced human monocyte chemotaxis.	2001-04	11321360
Mechanisms of inverse agonism of antipsychotic drugs at the D(2) dopamine receptor: use of a mutant D(2) dopamine receptor that adopts the activated conformation.	2001-04	11299312
Human immunodeficiency virus type 1 Tat protein decreases cyclic AMP synthesis in rat microglia cultures.	2001-04	11299302
Signals from cone photoreceptors to L-type horizontal cells are differentially modulated by low calcium in carp retina.	2001-04	11298802
Characterization of human, dog and rabbit corpus cavernosum type 5 phosphodiesterases.	2001-03-16	11388700
Ex vivo evidence that the phosphodiesterase inhibitor IBMX attenuates the up-regulation of PAR-2 in the endotoxemic rat aorta.	2001-03-15	11370637
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline.	2001-03	11465391
Generation of reactive oxygen species by xanthine derivatives in MDA-MB-231 human breast cancer cells.	2001-03	11437100
Monocyte chemoattractant protein-1 is expressed in pancreatic islets from prediabetic NOD mice and in interleukin-1 beta-exposed human and rat islet cells.	2001-03	11317664
Functional integrity of the vesicle transporting machinery is required for complete activation of cFTR expressed in xenopus laevis oocytes.	2001-03	11316271
Forskolin modulation of desensitization at GABA(A) and glycine receptors is not mediated by cAMP-dependent protein kinase in isolated carp amacrine-like cells.	2001-03	11316256
The phorbol ester PMA and cyclic AMP activate different Cl(-) and HCO3(-) fluxes in C127 cells expressing CFTR.	2001-02-14	11342000
Insulin treatment improves islet function in type 2 diabetic Chinese hamsters.	2001	11453031

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:46:57 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:57 GMT 2025`
Record UNII	TBT296U68M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-165960

Preferred Name

English

ISOBUTYLMETHYLXANTHINE

Systematic Name

English

3-ISOBUTYL-1-METHYLXANTHINE

Systematic Name

English

IBMX

Common Name

English

XANTHINE, 3-ISOBUTYL-1-METHYL-

Systematic Name

English

3,7-DIHYDRO-3-ISOBUTYL-1-METHYL-1H-PURINE-2,6-DIONE

Systematic Name

English

SC 2964

Code

English

3-ISOBUTYL-1-METHYL-XANTHINE

Systematic Name

English

SC-2964

Code

English

1-METHYL-3-ISOBUTYLXANTHINE

Systematic Name

English

1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1-METHYL-3-(2-METHYLPROPYL)-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

IBMX