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A5883

Sigma-Aldrich

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:
1123-54-2
Molecular Weight:
136.11
Beilstein/REAXYS Number:
141551
EC Number:
214-375-5
MDL number:
MFCD00005697
UNSPSC Code:
12352202
PubChem Substance ID:
24891030

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

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A Sahota et al.
Mutation research, 180(1), 81-87 (1987-09-01)
Spontaneous and ethyl methanesulfate induced mutants of Saccharomyces cerevisiae, with partial and complete deficiency of adenine phosphoribosyltransferase (APRT, EC 2.4.2.7), were isolated by selection for resistance to 8-azaadenine. Matings between totally deficient mutants and tester strain resulted in diploid heterozygotes
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
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