5667-20-9

Basic information

• Product Name: 6-N-HYDROXYLAMINOPURINE
• Synonyms: 6-hydroxyaminopurine;6-hydroxylaminopurine;n-hydroxy-1h-purin-6-amin;n-hydroxy-adenin;6-N-HYDROXYLAMINOPURINE;AURORA KA-540;N-hydroxy-1H-adenine;6-(Hydroxyamino)-9H-purine
• CAS NO: 5667-20-9
• Molecular Formula: C₅H₅N₅O
• Molecular Weight: 151.13
• EINECS: 227-125-5
• Product Categories: nucleoside
• Mol File: 5667-20-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 260 °C (decomp)
• Boiling Point: 273.11°C (rough estimate)
• Flash Point: 155.4°C
• Appearance: /
• Density: 1.4456 (rough estimate)
• Vapor Pressure: 9.79E-06mmHg at 25°C
• Refractive Index: 1.9000 (estimate)
• Storage Temp.: Store at -20
• PKA: 12.20±0.20(Predicted)
• CAS DataBase Reference: 6-N-HYDROXYLAMINOPURINE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-N-HYDROXYLAMINOPURINE(5667-20-9)
• EPA Substance Registry System: 6-N-HYDROXYLAMINOPURINE(5667-20-9)

Safety Data

• Hazardous Substances Data: 5667-20-9(Hazardous Substances Data)

Usage

Uses

6-Hydroxyaminopurine, a metabolite of Adenine is reported to be capable of inducing reversions in wild type, as well as in pso and rad6-1 mutant strains, indicating that this drug may act as a direct mutagen in yeast.

Definition

ChEBI: A member of the class of 6-aminopurinnes that is adenine in which one of the exocyclic amino hydrogens is replaced by a hydroxy group.

Synthesis Reference(s)

Journal of the American Chemical Society, 80, p. 3932, 1958 DOI: 10.1021/ja01548a033

InChI:InChI=1/C5H5N5O/c11-10-5-3-4(7-1-6-3)8-2-9-5/h1-3,11H,(H,6,7,8,9,10)

Upstream product

• 87-42-3 6-chloro-7H-purine 

Downstream Products

• 73-24-5 7H-purin-6-ylamine 

Relevant articles and documents

Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family

Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.

Purine N-oxides. XXVI. The synthesis and properties of 6-halogenopurine 3-N-oxides.

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