3-Isobutyl-1-methylxanthine

Base Information

• Chemical Name: 3-Isobutyl-1-methylxanthine
• CAS No.: 28822-58-4
• Molecular Formula: C10H14N4O2
• Molecular Weight: 222.247
• Hs Code.: 29335990
• European Community (EC) Number: 249-259-3
• NSC Number: 165960
• UNII: TBT296U68M
• DSSTox Substance ID: DTXSID0040549
• Nikkaji Number: J107.263C
• Wikipedia: IBMX
• Wikidata: Q223093
• Pharos Ligand ID: LJBJZDMX9VVX
• Metabolomics Workbench ID: 55031
• ChEMBL ID: CHEMBL275084
• Mol file: 28822-58-4.mol

Synonyms:1 Methyl 3 isobutylxanthine;1-Methyl-3-isobutylxanthine;3 Isobutyl 1 methylxanthine;3-Isobutyl-1-methylxanthine;IBMX;Isobutyltheophylline

Chemical Property of 3-Isobutyl-1-methylxanthine

Chemical Property:

• Appearance/Colour: off-white
• Vapor Pressure: 3.89E-08mmHg at 25°C
• Melting Point: 200-201 °C(lit.)
• Refractive Index: 1.569
• Boiling Point: 445.6 °C at 760 mmHg
• PKA: 8.61±0.70(Predicted)
• Flash Point: 223.3 °C
• PSA: 72.68000
• Density: 1.278 g/cm³
• LogP: 0.07930
• Storage Temp.: −20°C
• Solubility.: DMSO: 1 M with gentle warming
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 222.11167570
• Heavy Atom Count: 16
• Complexity: 318

Purity/Quality:

98%, ^*data from raw suppliers

IBMX ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CN1C2=C(C(=O)N(C1=O)C)NC=N2
• 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
• Uses: A nonspecific inhibitor of phosphodiesterases phosphodiesterase inhibitor 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.

Technology Process of 3-Isobutyl-1-methylxanthine

There total 11 articles about 3-Isobutyl-1-methylxanthine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

7-Pivalyloxymethyl-1-methyl-3-isobutylxanthine (73018-01-6) → 3,7-dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione (28822-58-4)

Guidance literature:

hydrolysis;

DOI:10.1021/jo01297a048

Reference yield:

→ 3,7-dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione (28822-58-4) + [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1)

Guidance literature:

Reference yield:

1-methylxanthine (6136-37-4) → 3,7-dihydro-1-methyl-3-(2-methylpropyl)-1H-purine-2,6-dione (28822-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 41 percent / Na₂CO₃ / dimethylformamide / 17 h

2: 91 percent

3: 76 percent / hydrolysis

With sodium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/jo01297a048

upstream raw materials:

formic acid

5,6-diamino-1-isobutyl-3-methyl-1H-pyrimidine-2,4-dione

7-Pivalyloxymethyl-1-methyl-3-isobutylxanthine

7-Benzyl-3-isobutyl-1-methylxanthine

Downstream raw materials:

(3-isobutyl-1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-acetic acid

7-(2,3-Dihydroxy-propyl)-3-isobutyl-1-methyl-3,7-dihydro-purine-2,6-dione

7-Dimethoxymethyl-3-isobutyl-1-methyl-3,7-dihydro-purine-2,6-dione

3-(3-Isobutyl-1-methyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-propionic acid

Refernces

• 1、 -. "Method for Distinguishing Mesenchymal Stem Cell Using Molecular Marker and Use Thereof". . . Retrieved 2009/09/28.
• 2、 Merlos,Gomez,Vericat,Bartroli,Garcia-Rafanell,Forn. "Structure-activity relationships in a series of xanthine derivatives with antibronchoconstrictory and bronchodilatory activities". . p. 653 - 658. Retrieved 2007/10/02.