A nucleotide metabolite
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Product Categories

Product Type

Biochemicals
Nucleotides/Nucleosides

Research Area

7-Methylguanine

Item No. 18161

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-1,7-dihydro-7-methyl-6H-purin-6-one
CAS Number
578-76-7
Synonyms
  • Epiguanine
  • 2-Amino-7-methylhypoxanthine
  • N7-Methylguanine
  • NSC 193444
  • NSC 19647
Molecular Formula
C6H7N5O
Formula Weight
165.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
1 M NaOH: 50 mg/ml
λmax
252, 281 nm
SMILES
O=C1C2=C(N=CN2C)NC(N)=N1
InChi Code
InChI=1S/C6H7N5O/c1-11-2-8-4-3(11)5(12)10-6(7)9-4/h2H,1H3,(H3,7,9,10,12)
InChi Key
FZWGECJQACGGTI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $36

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    100 mg

    $68

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    250 mg

    $134

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    500 mg

    $236

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    Product Description

    7-Methylguanine is a metabolite of the natural purine base whose N9 position is available for chemical modifications.1 This genotoxic adduct can be generated by DNA methylation and has been used as a probe of protein-DNA interactions and for DNA sequencing methods.2 It is also considered to be a carcinogenic biomarker for cigarette smoking that is detectable in urine.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kozma, A., Ibáñez, S., Silaghi-Dumitrescu, R., et al. 7-Methylguanine: Protonation, formation of linkage isomers with trans-(NH3)2Pt(II), and base pairing properties. Dalton Trans. 41, 6094-6103 (2012).

    2. Lee, S., Bowman, B.R., Ueno, Y., et al. Synthesis and structure of duplex DNA containing the genotoxic nucleobase lesion N7-methylguanine. J. Am. Chem. Soc. 130(35), 11570-11571 (2008).

    3. Lee, H.L., Hsueh, Y.M., Chung, C.J., et al. Correlation between the urine profile of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolites and N7-methylguanine in urothelial carcinoma patients. Cancer Epigemiol. Biomarkers Prev. 17(12), 3390-3395 (2008).