Purin-6(1H)-on
HYPOXANTHINE · 9H-PURIN-6-OL · Hypoxanthine,99% · Hypoxanthine-d4 · Hypoxanthine, 99.5% · 3,7-dihydropurin-6-one · Azathioprine EP Impurity F · 1,7-DIHYDRO-6H-PURIN-6-ONE
Identifikatoren & physikalische Daten
| CAS No. | 68-94-0 |
|---|---|
| Summenformel | C5H4N4O |
| Durchschnittliche Molmasse | 136,11 g/mol |
| Monoisotopische Masse | 136,03851076 g/mol |
| SMILES | O=c1nc[nH]c2nc[nH]c12 |
| InChIKey | FDGQSTZJBFJUBT-UHFFFAOYSA-N |
| PubChem CID | 790 |
| DTXSID | DTXSID8045983 |
| Lokaler Name | Purin-6(1H)-on |
Chemische & physikalische Eigenschaften
| XLogP | -1,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 70,1 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 190 |
| Arzneimittel | Pharmaceutical |
| LogP (Verteilungskoeffizient) | -1.11 |
| Löslichkeit | 0.7 mg/mL1 M NaOH: 25 mg/mLpractically insoluble |
| Schmelzpunkt | 150 °C>300 °C (lit.) |
| Physical Description | Solid |
| Collision Cross Section | 135.9 Ų [M+Na]+ |
| Siedepunkt | 250.36°C (rough estimate) |
| Dichte | 1.4295 (rough estimate) |
| Brechungsindex | 1.8500 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | 8.7(at 25℃) |
| Farbe | Colorless to yellow to brown, darken on storage with no loss of purity |
| Geruch | Odorless |
| Biologische Quelle | synthetic (organic) |
| Spezifische Wärmekapazität | Cp(crystal): 0.99 J/(g·K), at 25℃ |
| Merck | 14,4869 |
| BRN | 5811 |
| InChI | 1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10) |
| InChIKey | FDGQSTZJBFJUBT-UHFFFAOYSA-N |
| SMILES | O=C1NC=Nc2nc[nH]c12 |
| LogP (Verteilungskoeffizient) | -0.910 (est) |
| CAS Datenbank | 68-94-0(CAS DataBase Reference) |
| NIST chemische Informationen | Hypoxanthine(68-94-0) |
| EPA chemische Informationen | Hypoxanthine (68-94-0) |
Sicherheit & Vorschriften
| Treatment | Chronic Exposure: Kidney dialysis is usually needed to relieve the symptoms of xanthine toxicity until normal kidney function can be restored. Acute Exposure: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. |
|---|---|
| Gesundheitliche Auswirkungen | As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present. Chronically high concentrations of hpyoxanthine can lead to health problems such as renal failure and xanthine kidney stones, one of the rarest types of kidney stones. Chronically high levels of hypoxanthine are associated with at least 4 inborn errors of metabolism including: Xanthinuria type I, Xanthuria type II, Molybdenium Cofactor Deficiency, and Xanthinuria. |
| Expositionspfade | Endogenous, Ingestion, Dermal (contact) |
| Toxizitätsübersicht | Hypoxanthine is a poorly soluble compound. As a result high concentrations of serum hypoxanthine can lead to the formation of kidney stones which can, over the long term, induce kidney failure. |
| Signs and Symptoms | May lead to arthropathy, myopathy, crystal nephropathy, urolithiasis, or renal failure. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29335990 |
| RTECS-Nr. | UP0791000 |
| R-Sätze (R) |
Anwendungen & Verwendung
Beschreibung
Hypoxanthine is a naturally occurring purine derivative and intermediate in the synthesis of uric acid. It is elevated in the spinal fluid of patients with Lesch-Nyhan syndrome, a metabolic disorder whose symptoms include cerebral palsy, cognitive deficits, motor dysfunction, self-mutilation, and hyperuricemia. Injection of hypoxanthine (10 μM) increases succinate dehydrogenase and complex II activities and decreases cytochrome c oxidase activity, resulting in neuroenergetic impairment, ATP depletion, and cellular apoptosis in rat striatum. It is also used to induce hyperuricemia in mice for use in the development of hypouricemic agents.
Verwenden
A naturally occurring purine derivative. Pharmaceuticals, Intermediates & Fine Chemicals