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I7018

3-Isobutyl-1-methylxanthine

Name: 3-Isobutyl-1-methylxanthine
Brand: SIGMA

≥99%, Phosphodiesterase inhibitor

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₄N₄O₂

CAS Number:

28822-58-4

Molecular Weight:

222.24

NACRES:

NA.77

PubChem Substance ID:

24896107

UNSPSC Code:

12352202

EC Number:

249-259-3

MDL number:

MFCD00005584

Beilstein/REAXYS Number:

247859

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Properties

Product Name

3-Isobutyl-1-methylxanthine, BioUltra, ≥99%

product line

BioUltra

Quality Level

200

assay

≥99%

impurities

<0.005% Phosphorus (P)

ign. residue

<0.1%

mp

200-201 °C (lit.)

solubility

DMSO: soluble 1 M (with gentle warming)

anion traces

sulfate (SO₄^2-): <0.05%

cation traces

Al: <0.0005%, Ca: <0.005%, Cu: <0.0005%, Fe: <0.005%, K: <0.05%, Mg: <0.005%, NH₄⁺: <0.05%, Na: <0.005%, Pb: <0.001%, Zn: <0.0005%

storage temp.

−20°C

SMILES string

CC(C)CN1C(=O)N(C)C(=O)c2[nH]cnc12

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)

InChI key

APIXJSLKIYYUKG-UHFFFAOYSA-N

Gene Information

rat ... Adora1(29290), Adora2a(25369)

Description

Application

3-Isobutyl-1-methylxanthine, an inhibitor of adenosine 3′,5′-cyclic monophosphate phosphodiesterase (cAMP PDE), has been used:

for adipogenic differentiation
in tissue culture
3T3-L1 preadipocyte differentiation(

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.

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.

Features and Benefits

Trace element testing by ICP
ICP testing for trace sulfur (as sulfate) and phosphorus (as phosphate) content
Ion chromatography testing for trace ammonium content

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Global Trade Item Number

SKU	GTIN
I7018-250MG	04061835557400
I7018-100MG	04061835557394
I7018-1G	04061833858011