A5883
8-Azaadenine
≥99%
Synonym(s):
6-Amino-8-azapurine, 8-Aza-6-aminopurine
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About This Item
Empirical Formula (Hill Notation):
C4H4N6
CAS Number:
Molecular Weight:
136.11
Beilstein:
141551
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
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Assay
≥99%
form
powder
mp
>300 °C (lit.)
solubility
1 M NaOH: 50 mg/mL, clear, colorless to faintly yellow
storage temp.
2-8°C
SMILES string
Nc1ncnc2nn[nH]c12
InChI
1S/C4H4N6/c5-3-2-4(7-1-6-3)9-10-8-2/h1H,(H3,5,6,7,8,9,10)
InChI key
HRYKDUPGBWLLHO-UHFFFAOYSA-N
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General description
Base pairs of azaadenine with thymine (and azaguanine with cytosine) are found by ab initio calculation to be up to 7 kcal/mol more stable than natural AT (and GC) base pairs.
Storage Class Code
13 - Non Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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G Biagi et al.
Farmaco (Societa chimica italiana : 1989), 50(1), 13-19 (1995-01-01)
Comparison of the affinity towards adenosine receptors of 2-phenyl-8-azaadenosines, bearing a lipophilic substituent on N(6), with the corresponding 2-phenyl-8-azaadenines was carried out. The compounds have good A1 affinity and high A1 selectivity. The obtained Ki(rib)/Ki(benz) ratios for A1 receptors, which
Giuliana Biagi et al.
Farmaco (Societa chimica italiana : 1989), 57(3), 221-233 (2002-05-07)
erythro-2-Phenyl-9-(2-hydroxy-3-nonyl)adenine and its 8-aza analog were prepared and showed a very high inhibitory activity towards adenosine deaminase (ADA), with Ki 0.55 and 1.67 nM, respectively, and high affinity for A1 adenosine receptors, with Ki 28 and 2.8 nM, respectively. To
D J Chen et al.
Environmental mutagenesis, 4(4), 457-467 (1982-01-01)
A chinese hamster ovary (CHO) cell line heterozygous at the adenine phosphoribosyl transferase (APRT) locus was used for selection of induced mutants resistant to 8-azaadenine (8AA), 6-thioguanine (6TG), ouabain (OUA), emetine (EMT) and diphtheria toxin (DIP). The expression times necessary
A E Simon et al.
Molecular and cellular biology, 3(10), 1703-1710 (1983-10-01)
A two-step model to explain the high frequency of mutation at the diploid adenine phosphoribosyltransferase (aprt) locus in CHO cells has been proposed previously (Simon et al., Mol. Cell. Biol. 2:1126-1133, 1982). This model indicates that two distinct classes of
M I Nieto et al.
Nucleosides & nucleotides, 17(7), 1255-1266 (1998-08-26)
Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 5-7), 8-azapurine (compounds 9 and 10) or pyrimidine (compound 13) base on the amino group of (1R,cis)-3-(aminomethyl)-1,2,2-trimethylcyclopentylmethanol (2). The antiviral activity of compounds 5-7, 10 and 13, and their
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