3-Isobutyl-1-methylxanthine

HCID 3758CAS 28822-58-4

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Grundinformationen

Standard-SMILES: CC(C)Cn1c(=O)n(C)c(=O)c2[nH]cnc21
InChIKey: APIXJSLKIYYUKG-UHFFFAOYSA-N
Summenformel: C10H14N4O2
Durchschnittliche Molmasse: 222,24 g/mol
Monoisotopische Masse: 222,1116757

Namen und Bezeichner

Bevorzugter Name: 3-Isobutyl-1-methylxanthine
IUPAC: 1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dione
Englischer Name: 3-Isobutyl-1-methylxanthine
Summenformel: C10H14N4O2
Molmasse: 222.24

Namen und Synonyme

3-Isobutyl-1-methylxanthineIBMX28822-58-4isobutylmethylxanthine1-METHYL-3-ISOBUTYLXANTHINE1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-3-(2-methylpropyl)-Xanthine, 3-isobutyl-1-methyl-3-Isobutyl-1-methyl-3,7-dihydro-1H-purine-2,6-dione3-Isobutyl-1-methyxanthine3-isobutyl-1-methyl-7H-xanthine1-methyl-3-(2-methylpropyl)-7H-purine-2,6-dioneSC-2964

Weitere Namen anzeigen

MIXIMXI5879-1GNSC 165960I5879-100MGI5879-250MGIBMX(NSC165960

TBT296U68MCHEBI:347951-methyl-3-(2-methylpropyl)-3,7-dihydro-1H-purine-2,6-dioneNSC-165960SC 2964DTXSID0040549Isobutyltheophylline3 Isobutyl 1 methylxanthine

Datenbank-Bezeichner

CAS: 28822-58-4
PubChem CID: 3758
DTXSID: DTXSID0040549
ChEMBL: CHEMBL275084
ChEBI: CHEBI:34795
UNII: TBT296U68M
EC Number: 249-259-3
Nikkaji: J107.263C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,5
Polarare Oberfläche (TPSA): 69,3 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 2
Schwere Atome: 16
Formalladung: 0
Komplexität: 318

Experimentelle und physikochemische Eigenschaften

Kovats Retention Index2150；2150；2150

Collision Cross Section147.8 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt: 200 · 200-201 °C(lit.)
Siedepunkt: 363.42 °C · 363.42°C (rough estimate)
Dichte: 1.2042 · 1.2042 (rough estimate)
Brechungsindex: 1.65 · 1.6500 (estimate)
storage temp.: -20 °C · -20°C
Löslichkeit: 1 M · DMSO: 1 M with gentle warming
Aggregatzustand: powder
pka: 8.61 · 8.61±0.70(Predicted)
Farbe: off-white
BRN: 247859 · 247859
Stabilität: 2 years · 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.
InChI: 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)
InChIKey: APIXJSLKIYYUKG-UHFFFAOYSA-N
SMILES: N1C2=C(N(CC(C)C)C(=O)N(C)C2=O)NC=1
CAS Datenbank: 28822 · 28822-58-4(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 70 reports by companies from 2 notifications to the ECHA C&L Inventory.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Sicherheitsdaten

wgk: 3
hs_code: 29335990
RTECS-Nr.: ZD8500000
risk_code: 22
hazard_code: Xn
safety_code: 24/25
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological ClassificationCompounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.

Anwendungen · 1 Eintrag

Verwenden3-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.