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Purin-6(1H)-on

CID 790

HCID 790
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TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
68-94-0
Standard-SMILES
O=c1nc[nH]c2nc[nH]c12
InChIKey
FDGQSTZJBFJUBT-UHFFFAOYSA-N
Summenformel
C5H4N4O
Durchschnittliche Molmasse
136,11 g/mol
Monoisotopische Masse
136,03851076

Überblick

Hypoxanthine is a purine and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway.

Namen und Bezeichner

Bevorzugter Name
CID 790
IUPAC
3,7-dihydropurin-6-one
Lokaler Name
Purin-6(1H)-on
Englischer Name
6-Hydroxypurine
Summenformel
C5H4N4O
Molmasse
136.11

Namen und Synonyme

HYPOXANTHINE9H-PURIN-6-OLHypoxanthine,99%Hypoxanthine-d4Hypoxanthine, 99.5%3,7-dihydropurin-6-oneAzathioprine EP Impurity F1,7-DIHYDRO-6H-PURIN-6-ONE6H-Purin-6-one, 1,7-dihydro-6H-Purin-6-one, 1,9-dihydro-

Datenbank-Bezeichner

CAS
68-94-0
PubChem CID
790
DTXSID
DTXSID8045983

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-1,1
Polarare Oberfläche (TPSA)
70,1 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
10
Formalladung
0
Komplexität
190

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceutical
LogP-1.11
Solubility0.7 mg/mL
Melting Point150 °C
Physical DescriptionSolid
Collision Cross Section135.9 Ų [M+Na]+

Physikochemische Eigenschaften

Schmelzpunkt
300 °C · >300 °C (lit.)
Siedepunkt
250.36 °C · 250.36°C (rough estimate)
Dichte
1.4295 · 1.4295 (rough estimate)
Brechungsindex
1.85 · 1.8500 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
1 M · 1 M NaOH: 25 mg/mL
Aggregatzustand
powder
pka
8.7 · 8.7(at 25℃)
Farbe
Colorless to yellow to brown, darken on storage with no loss of purity
Geruch (Odor)
Odorless
Biologische Quelle
synthetic (organic)
Wasserlöslichkeit
practically insoluble
Spezifische Wärmekapazität
0.99 J/ · Cp(crystal): 0.99 J/(g·K), at 25℃
Merck
14 · 14,4869
BRN
5811 · 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
-0.91 · -0.910 (est)
CAS Datenbank
68 · 68-94-0(CAS DataBase Reference)
NIST chemische Informationen
Hypoxanthine(68-94-0)
EPA chemische Informationen
Hypoxanthine (68-94-0)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Treatment · 1 Eintrag

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.

Health Effects · 1 Eintrag

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.

Exposure RoutesEndogenous, Ingestion, Dermal (contact)
Toxicity SummaryHypoxanthine 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 SymptomsMay lead to arthropathy, myopathy, crystal nephropathy, urolithiasis, or renal failure.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Sicherheitsdaten

wgk
3
tsca
TSCA listed
hs_code
29335990
RTECS-Nr.
UP0791000
risk_code
36/37/38-22-40
Toxizität
LD50 intraperitoneal in mouse: 750mg/kg
hazard_code
Xn
hazard_note
Harmful
safety_code
22-24/25-37/39-26-36
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Under normal circumstances hypoxanthine is readily converted to uric acid. The enzyme xanthine oxidase makes uric acid from xanthine and hypoxanthine, which in turn are produced from other purines. In humans and higher primates, uric acid is the final oxidation (breakdown) product of purine metabolism and is excreted in urine.

Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)

Verwendung und Herstellung

UsesNaturally produced by the body (endogenous).
Anwendungen · 2 Einträge

BeschreibungHypoxanthine 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.

VerwendenA naturally occurring purine derivative. Pharmaceuticals, Intermediates & Fine Chemicals

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Natriumethanolat6-Amino-2-thiouracilhydratEthylcyanacetatThioharnstoff

Nachgelagerte Produkte

6-Dimethylaminopurin6-n-HeptylmercaptopurineAdeninMercaptopurinN-Hexyl-1H-adenin6-Ethoxy-1H-purin1H-Purin-6-carbonitril6-benzylaminopurine6-EthylmercaptopurineAciclovir6-Brom-1H-purinN6-Cyclohexyladenosine6-Mercaptopurine monohydrateN-(2-Hydroxyethyl)adenosine6-Butoxy-1H-purinPurinBenzyl(purin-6-yl)amin6-Iodpurin6-benzylaminopurine hydrochloride

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Ergänzende Hinweise

DefinitionChEBI: A purine nucleobase that consists of purine bearing an oxo substituent at position 6.

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