3,7-Dihydro-1,7-dimethyl-1H-purin-2,6-dion
PARAXANTHINE · Paraxanthin · Caffeine EP Impurity F · 1,7-dimethyl-3H-purine-2,6-dione · 1,7-Dimethyl-1H-purine-2,6-dione, 1,7-Dimethylxanthine, 2,6-Dihydroxy-1,7-dimethylpurine, Paraxanthine · 1,7-diMethyl-1H-purine-2,6(3H,7H)-dione · Paraxanthine-d3 · Caffeine IMpurity F
Identifikatoren & physikalische Daten
| CAS No. | 611-59-6 |
|---|---|
| Summenformel | C7H8N4O2 |
| Durchschnittliche Molmasse | 180,16 g/mol |
| Monoisotopische Masse | 180,06472551 g/mol |
| SMILES | Cn1c(=O)[nH]c2ncn(C)c2c1=O |
| InChIKey | QUNWUDVFRNGTCO-UHFFFAOYSA-N |
| PubChem CID | 4687 |
| ChEMBL | CHEMBL1158 |
| ChEBI | CHEBI:25858 |
| EC No. | 210-271-9 |
| DTXSID | DTXSID2052281 |
| Lokaler Name | 3,7-Dihydro-1,7-dimethyl-1H-purin-2,6-dion |
Chemische & physikalische Eigenschaften
| XLogP | -0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 67,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 267 |
| Löslichkeit | >27 [ug/mL] (The mean of the results at pH 7.4)ethanol: 0.6mg/mL |
| Schmelzpunkt | 351 - 352 °C294-296 °C (lit.) |
| Physical Description | Faint yellow fine crystals[MSDSonline]Solid |
| Collision Cross Section | 134.2 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID2052281]136.8 Ų [M-H]- [CCS Type: DTIonization: ESI-149.5 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]134 Ų [M+H]+ [CCS Type: DT138.7 Ų [M+H]+ [CCS Type: DT130.85 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]137.69 Ų [M+K]+ [CCS Type: TW125.98 Ų [M+H-H2O]+ [CCS Type: TW138.86 Ų [M+Na]+ [CCS Type: TW132.4 Ų [M+H]+ [CCS Type: TW135.63 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]133.24 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| Siedepunkt | 312.97°C (rough estimate) |
| Dichte | 1.3640 (rough estimate) |
| Brechungsindex | 1.6700 (estimate) |
| Flammpunkt | 9℃ |
| Lagerbedingungen | room temp |
| Aggregatzustand | solid |
| pKa (Säurekonstante) | pKa 8.5 (Uncertain) |
| Farbe | white |
| BRN | 197907 |
| Stabilität | Store tightly sealed at RT |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONING |
| InChI | InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13) |
| InChIKey | QUNWUDVFRNGTCO-UHFFFAOYSA-N |
| SMILES | N1(C)C2=C(NC(=O)N(C)C2=O)N=C1 |
| EPA chemische Informationen | 1H-Purine-2,6-dione, 3,7-dihydro-1,7-dimethyl- (611-59-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 6.7% (3 of 45) of reports.WarningH302 (93.3%): 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 45 reports by companies from 3 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 3 of 45 reports by companies.There are 2 notifications provided by 42 of 45 reports by companies with hazard statement code(s).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. |
|---|---|
| Gefahrenübersicht | A skin, eye, and respiratory tract irritant[MSDSonline] |
| Hazard Classes and Categories | Acute Tox. 4 (93.3%) |
| USGS Health-Based Screening Levels for Evaluating Water-Quality | 1,7-DimethylxanthinePharmaceuticalSmith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN1230 - class 3 - PG 2 - Methanol, solution |
| Zollcode | 2933.59.9500 |
| RTECS-Nr. | RV9380000 |
| R-Sätze (R) | 22-39/23/24/25-23/24/25-11 |
| Toxizität | mmo-esc 150 mg/L CSHSAZ 16,337,52 |
| Gefahrensymbole | Xn,T,F |
| Sicherheitshinweise (S) | 22-24/25-45-36/37-16-7 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 Oral |
Anwendungen & Verwendung
Beschreibung
Paraxanthine is an inhibitor of phosphodiesterase 9 (PDE9) and an antagonist of adenosine receptors A1 and A2 (Kis = 35 and 22 μM, respectively in equine forebrain tissues). It is the main metabolite of caffeine in humans, making up 80% of the three dimethylxanthine metabolites produced by caffeine demethylation. Paraxanthine increases locomotor activity and counteracts adenosine receptor agonist-induced motor depression in rats not habituated to caffeine. At a dose of 30 mg/kg, paraxanthine induces a significant increase in striatal cGMP and extracellular striatal dopamine concentrations in vivo. It also promotes wakefulness and increases locomotor activity and core temperature in narcoleptic transgenic mice without increasing behavioral anxiety.
Verwenden
1,7-Dimethylxanthine has been used for the quantification of caffeine by high-performance liquid chromatography (HPLC).