ChemicalBook > CAS DataBase List > 3-ISOBUTYL-1-METHYLXANTHINE

3-ISOBUTYL-1-METHYLXANTHINE

Product Name
3-ISOBUTYL-1-METHYLXANTHINE
CAS No.
28822-58-4
Chemical Name
3-ISOBUTYL-1-METHYLXANTHINE
Synonyms
IBMX;MIX;3-Isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione;IMX;SC 2964;NSC 165960;IBMX(NSC165960;3-Isobutyl-1-methylx;Methylisobutylxanthine;Isobutylmethylxanthine
CBNumber
CB6263892
Molecular Formula
C10H14N4O2
Formula Weight
222.24
MOL File
28822-58-4.mol
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3-ISOBUTYL-1-METHYLXANTHINE Property

Melting point:
200-201 °C(lit.)
Boiling point:
363.42°C (rough estimate)
Density 
1.2042 (rough estimate)
refractive index 
1.6500 (estimate)
storage temp. 
-20°C
solubility 
DMSO: 1 M with gentle warming
form 
powder
pka
8.61±0.70(Predicted)
color 
off-white
BRN 
247859
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
InChIKey
APIXJSLKIYYUKG-UHFFFAOYSA-N
CAS DataBase Reference
28822-58-4(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn
Risk Statements 
22
Safety Statements 
24/25
WGK Germany 
3
RTECS 
ZD8500000
HS Code 
29335990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P330Rinse mouth.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
410957
Product name
3-Isobutyl-1-methylxanthine
Packaging
250mg
Price
$85.2
Updated
2024/03/01
Sigma-Aldrich
Product number
410957
Product name
3-Isobutyl-1-methylxanthine - CAS 28822-58-4 - Calbiochem
Purity
A cell-permeable, non-specific inhibitor of cAMP and cGMP phosphodiesterases (IC?? = 2-50 μM).
Packaging
1g
Price
$230
Updated
2024/03/01
Alfa Aesar
Product number
J64598
Product name
3-Isobutyl-1-methylxanthine
Packaging
100mg
Price
$54.3
Updated
2024/03/01
Cayman Chemical
Product number
13347
Product name
IBMX
Purity
≥98%
Packaging
100mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
13347
Product name
IBMX
Purity
≥98%
Packaging
1g
Price
$160
Updated
2024/03/01
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3-ISOBUTYL-1-METHYLXANTHINE Chemical Properties,Usage,Production

Description

IBMX (28822-58-4) is a pan-specific inhibitor of phosphodiesterases (IC50=2-50 μM). Inhibition of PDEs leads to increased concentration of intracellular cAMP which activates PKA.2?IBMX does not inhibit PDE8 or PDE9.3?Weak adenosine receptor antagonist.4

Chemical Properties

White Needles with Yellow Cast

Uses

A nonspecific inhibitor of phosphodiesterases

Uses

phosphodiesterase inhibitor

Uses

3-Isobutyl-1-methylxanthine is used in inhibition of phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50 = 1.3 uM). Also inhibits ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. Inhibits the growth of carcinoma cells both in vivo and in vitro in mice.

Definition

ChEBI: 3-isobutyl-1-methyl-9H-xanthine is a 3-isobutyl-1-methylxanthine. It is functionally related to a 9H-xanthine. It is a tautomer of a 3-isobutyl-1-methyl-7H-xanthine.

General Description

3-isobutyl-1-methylxanthine/IBMX is a non-selective, non-specific inhibitor of cAMP and cGMP phosphodiesterases. IBMX can induce melanogenesis, and can be used as a positive control in melanogenesis research. In oocyte research, IBMX assists in maintaining the germinal vesicle (GV) arrest of prophase I oocytes.

Biological Activity

Phosphodiesterase inhibitor (IC 50 values are 13, 18, 19, 32 and 50 μ M for PDE4, PDE3, PDE1, PDE5 and PDE2 respectively). Suppresses α -adrenoceptor-mediated 5-HT release from neuroendocrine epithelial cells (IC 50 = 1.3 μ M).

Biochem/physiol Actions

The increase in cAMP level as a result of phosphodiesterase inhibition by IBMX activates PKA, leading to decreased proliferation, increased differentiation, and induction of apoptosis. IBMX inhibits phenylephrine-induced release of 5-hydroxytryptamine from neuroendocrine epithelial cells of the airway mucosa (IC50: 1.3 μM). IBMX also serves as an adenosine receptor antagonist. IBMX has been shown to inhibit ion channels in the neuromuscular junction, GH3 cells, and vascular smooth muscle cells. IBMX induces calcium release from intracellular stores in sensory neurons.

storage

+4°C

Purification Methods

Recrystallise it from aqueous EtOH. [Beilstein 26

References

1) Beavo et al. (1970), Effects of xanthine derivatives on lipolysis and on adenosine 3′,5′-monophosphate phosphodiesterase activity; Mol. Pharmacol., 6 597 2) Tomes et al. (1993), Isobutylmethylxanthine and other classical cyclic nucleotide phosphodiesterase inhibitors affect cAMP-dependent protein kinase activity; Cell Signal., 5 615 3) Soderling et al. (2000), Regulation of cAMP and cGMP signaling: new phosphodiesterases and new functions; Curr. Opin. Cell Biol., 12 174 4) Daly et al. (1987), Adenosine receptors: development of selective agonists and antagonists; Prog. Clin. Biol. Res., 230 41

3-ISOBUTYL-1-METHYLXANTHINE Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 3-ISOBUTYL-1-METHYLXANTHINE manufacturers

Career Henan Chemical Co
Product
3-ISOBUTYL-1-METHYLXANTHINE 28822-58-4
Price
US $8.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10tons
Release date
2018-12-24

28822-58-4, 3-ISOBUTYL-1-METHYLXANTHINERelated Search:

Verofylline 3-ISOBUTYL-1-METHYLXANTHINE Cipamfylline 8-[2-(4-benzhydrylpiperazin-1-yl)ethyl]-1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione 8-METHOXYMETHYL-3-ISOBUTYL-1-METHYLXANTHINE 1-METHYLXANTHINE Mexafylline 8-Dicyclopropylmethyl-3-isobutyl-1-methylxanthine 8-Phenyl-3-isobutyl-1-methylxanthine IBMX (3-Isobutyl-1-methylxanthine) 7-BENZYL-3-ISOBUTYL-1-METHYLXANTHINE 8-Bromo-3-isobutyl-1-methylxanthine 7-Propyl-3-isobutyl-1-methylxanthine 1-ISOBUTYL-1-METHYLXANTHINE 1-Isobutyl-3-methylxanthine 1H-Purine-2,6-dione, 3,7-dihydro-8-methyl-3-(2-methylpropyl)-1-propyl- 1,3-Diisobutyl-8-methylxanthine 1,3-Bis(cyclopropylmethyl)-8-(dicyclopropylmethyl)xanthine

  • 1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)-
  • 3,7-dihydro-1-methyl-3-(2-methylpropyl)-1h-purine-6-dione
  • 3-Isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione
  • 3-Isobutyl-1-methylanxthine
  • 3-isobutyl-1-methyl-xanthin
  • IMX
  • Isobutylmethylxanthine
  • Methylisobutylxanthine
  • SC 2964
  • Xanthine, 3-Isobutyl-1-methyl-
  • MIX
  • 1-METHYL-3-ISOBUTYL XANTHINE
  • IBMX
  • 1-Methyl-3-isobutylxanthine 3,7-Dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione 3-Isobutyl-1-methyl-2,6(1H,3H)-purinedione IBMX MIX
  • 3,7-Dihydro-1-methyl-3-(2-methy
  • 3-isobutyl-1-methyl-1H-purine-2,6(3H,9H)-dione
  • 3-isobutyl-1-methyl-3,9-dihydro-1H-purine-2,6-dione
  • 3-isobutyl-1-methyl-7H-purine-2,6-dione
  • 3-isobutyl-1-methyl-7H-purine-2,6-quinone
  • 3-Isobutyl-1-methyxanthine
  • 3-isobutyl-1-methyl-7H-xanthine
  • 3-Isobutyl-1-methylxanthine - CAS 28822-58-4 - Calbiochem
  • IBMX(NSC165960
  • IMX; ISOBUTYLMETHYLXANTHINE; METHYLISOBUTYLXANTHINE; NSC165960; SC2964
  • 3,7-Dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione
  • 3-ISOBUTYL-1-METHYL-2,6(1H,3H)-PURINEDIONE
  • 3-ISOBUTYL-1-METHYLXANTHINE
  • 3-ISOBUTYL-I-METHYLXANTHINE
  • 3-ISOBUTYL-1-METHYLXANTHINE SIGMAULTRA
  • Isobutyl-1-methylxanthine
  • 3-ISOBUTYL-1-METHYLXANTHINE,ULTRAPURE
  • 3-Isobutyl-1-methylxanthine, HPLC 99%
  • 3-ISOBUTYL-1-METHYLXANTHINE (CRYSTALLINE)
  • 3,9-Dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione
  • NSC 165960
  • 3,7-dihydro-3-isobutyl-1-methyl-1H-purine-2,6-dione
  • 3-Isobutyl-1-methylxanthine 99+%
  • 3-Isobutyl-1-methylxanthine,1-Methyl-3-isobutylxanthine, 3,7-Dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione, 3-Isobutyl-1-methyl-2,6(1H,3H)-purinedione, IBMX
  • 3-Isobutyl-1-methylx
  • (3-isobutyl-1-Methylxanthine,IBMX)
  • 3-Isobutyl-1-Methylxanthine, 99+% 1GR
  • 3,9-Dihydro-1-Methyl-3-(2-Methylpropyl)-
  • 3-Isobutyl-1-Methyl-1H-purine-2,6(3H,7H)-dione
  • 1H-Purine-2,6-dione, 3,9-dihydro-1-methyl-3-(2-methylpropyl)-
  • 3-ISOBUTYL-1-METHYLXANTHINE USP/EP/BP
  • 1-methyl-3-(2-methylpropyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
  • IBMX,Phosphodiesterase (PDE),inhibit,Inhibitor
  • 3-isobutyl-1-methyl-9H-purine-2,6-dione
  • 28822-58-4
  • Non-specific inhibitor of cAMP and cGMP phosphodiesterases.
  • KETONE
  • BioChemical
  • Chiral Building Blocks
  • Cell Biology
  • Cell Signaling and Neuroscience
  • Asymmetric Synthesis
  • G Proteins and Cyclic Nucleotides
  • Cyclic Nucleotide Metabolism