Basic information
- CAS
68-94-0- Standard SMILES
O=c1nc[nH]c2nc[nH]c12- InChIKey
FDGQSTZJBFJUBT-UHFFFAOYSA-N- Molecular formula
- C5H4N4O
- Average molar mass
- 136.11 g/mol
- Monoisotopic mass
- 136.03851076
Overview
Hypoxanthine is a purine and a reaction intermediate in the metabolism of adenosine and in the formation of nucleic acids by the salvage pathway.
Names & identifiers
- Preferred name
- CID 790
- IUPAC
- 3,7-dihydropurin-6-one
- English name
- 6-Hydroxypurine
- Molecular formula
- C5H4N4O
- Molecular weight
- 136.11
Names & synonyms
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-
Database identifiers
- CAS
68-94-0- PubChem CID
- 790
- DTXSID
DTXSID8045983
Properties
Computed structural properties
- XLogP
- -1.1
- Topological polar surface area
- 70.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 190
Experimental & physicochemical properties
DrugsPharmaceutical
LogP-1.11
Solubility0.7 mg/mL
Melting Point150 °C
Physical DescriptionSolid
Collision Cross Section135.9 Ų [M+Na]+
Physicochemical properties
- Melting point
- 300 °C · >300 °C (lit.)
- Boiling point
- 250.36 °C · 250.36°C (rough estimate)
- Density
- 1.4295 · 1.4295 (rough estimate)
- refractive index
- 1.85 · 1.8500 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 1 M · 1 M NaOH: 25 mg/mL
- form
- powder
- pka
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
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.
Health Effects
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).
Chemistry & industry
Pharmacology
Metabolism/Metabolites
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)
Uses & manufacturing
UsesNaturally produced by the body (endogenous).
Applications
DescriptionHypoxanthine 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.
UsesA naturally occurring purine derivative. Pharmaceuticals, Intermediates & Fine Chemicals
UsesHypoxanthine is a nutrient additive for a variety of cell culture applications involving bacterial, parasite (Plasmodium falciparum) and animal cells. Hypoxanthine is a component of selection media used in hybridoma technologies.
Hypoxanthine, is used as a marker for energy perturbation in hypoxia/ ischemia. The compound has been used in studies as in indicator, along with uric acid and allantoin , of in vivo free radical reactions. It has been also used in DNA studies to investigate the destabilizing effect it has on DNA duplexes containing hypoxanthine as a base, in a gas phase versus a liquid phase. Hypoxanthine has also been used in studies along with 8-oxoguanine nucleotides to investigate their interaction with human DNA pol (DNA polymerase alpha) and DNA polymerase I from Bacillus stearothermophilus. It is also used as a pharmaceutical intermediate.
Related reactions
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Compound notes
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