7-Methyladenine
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 591118

CAS#: 935-69-3

Description: 7-Methyladenine is a potential marker for monitoring exposure to methylatingcarcinogens.


Chemical Structure

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7-Methyladenine
CAS# 935-69-3

Theoretical Analysis

MedKoo Cat#: 591118
Name: 7-Methyladenine
CAS#: 935-69-3
Chemical Formula: C6H7N5
Exact Mass: 149.0701
Molecular Weight: 149.16
Elemental Analysis: C, 48.32; H, 4.73; N, 46.95

Price and Availability

Size Price Availability Quantity
100.0mg USD 320.0 2 Weeks
500.0mg USD 820.0 2 Weeks
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Synonym: 7-Methyladenine; NSC 7857; NSC-7857; NSC7857

IUPAC/Chemical Name: 7H-Purin-6-amine, 7-methyl- (9CI)

InChi Key: HCGHYQLFMPXSDU-UHFFFAOYSA-N

InChi Code: InChI=1S/C6H7N5/c1-11-3-10-6-4(11)5(7)8-2-9-6/h2-3H,1H3,(H2,7,8,9)

SMILES Code: NC1=C2N(C)C=NC2=NC=N1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 149.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Harroun SG, Zhang Y, Chen TH, Ku CR, Chang HT. Biomarkers of cigarette smoking and DNA methylating agents: Raman, SERS and DFT study of 3-methyladenine and 7-methyladenine. Spectrochim Acta A Mol Biomol Spectrosc. 2017 Apr 5;176:1-7. doi: 10.1016/j.saa.2016.12.012. Epub 2016 Dec 15. PubMed PMID: 28061366.

2: Michelson AZ, Chen M, Wang K, Lee JK. Gas-phase studies of purine 3-methyladenine DNA glycosylase II (AlkA) substrates. J Am Chem Soc. 2012 Jun 13;134(23):9622-33. doi: 10.1021/ja211960r. Epub 2012 May 31. PubMed PMID: 22554094.

3: Tokuda S, Fukuda T, Kobayashi Y, Tanaka M, Matsui T. Effect of the uncharged imidazolium moiety in adenine on endothelium-independent relaxation in the contracted thoracic aorta of Sprague-Dawley rats. Biosci Biotechnol Biochem. 2012;76(4):828-30. Epub 2012 Apr 7. PubMed PMID: 22484931.

4: von Kügelgen I, Schiedel AC, Hoffmann K, Alsdorf BB, Abdelrahman A, Müller CE. Cloning and functional expression of a novel Gi protein-coupled receptor for adenine from mouse brain. Mol Pharmacol. 2008 Feb;73(2):469-77. Epub 2007 Nov 1. PubMed PMID: 17975009.

5: Gorzalka S, Vittori S, Volpini R, Cristalli G, von Kügelgen I, Müller CE. Evidence for the functional expression and pharmacological characterization of adenine receptors in native cells and tissues. Mol Pharmacol. 2005 Mar;67(3):955-64. Epub 2004 Dec 16. PubMed PMID: 15604413.

6: Cohen B, Hare PM, Kohler B. Ultrafast excited-state dynamics of adenine and monomethylated adenines in solution: implications for the nonradiative decay mechanism. J Am Chem Soc. 2003 Nov 5;125(44):13594-601. PubMed PMID: 14583057.

7: Birkeland NK, Anensen H, Knaevelsrud I, Kristoffersen W, Bjørås M, Robb FT, Klungland A, Bjelland S. Methylpurine DNA glycosylase of the hyperthermophilic archaeon Archaeoglobus fulgidus. Biochemistry. 2002 Oct 22;41(42):12697-705. PubMed PMID: 12379112.

8: Tudek B, Graziewicz M, Kazanova O, Zastawny TH, Obtułowicz T, Laval J. Mutagenic specificity of imidazole ring-opened 7-methylpurines in M13mp18 phage DNA. Acta Biochim Pol. 1999;46(3):785-99. PubMed PMID: 10698287.

9: Bjørås M, Klungland A, Johansen RF, Seeberg E. Purification and properties of the alkylation repair DNA glycosylase encoded the MAG gene from Saccharomyces cerevisiae. Biochemistry. 1995 Apr 11;34(14):4577-82. PubMed PMID: 7718559.

10: Mandel HG, Straw JA, Wenger LJ, Kusmierz JJ. The excretion of 7-methyladenine in the urine of rats exposed to carcinogenic methylating agents. Carcinogenesis. 1994 Jul;15(7):1393-8. PubMed PMID: 8033316.

11: Mandel HG, Kusmierz JJ, Dickens BF, Anderson LW. Quantitation of urinary 7-methyladenine by gas chromatography-mass spectrometry using isotopically labeled internal standards. Anal Biochem. 1994 Mar;217(2):292-7. PubMed PMID: 8203758.

12: O'Connor TR, Laval J. Human cDNA expressing a functional DNA glycosylase excising 3-methyladenine and 7-methylguanine. Biochem Biophys Res Commun. 1991 May 15;176(3):1170-7. PubMed PMID: 1645538.

13: Mandel HG, Straw JA, Farmer PB, Martin J. Chromatographic detection of 7-methyladenine in urine of rats administered N-methylnitrosourea: a potential marker for monitoring exposure to methylating carcinogens. Carcinogenesis. 1989 Apr;10(4):757-62. PubMed PMID: 2702723.

14: Starratt AN, Bond EJ. In vitro methylation of DNA by the fumigant methyl bromide. J Environ Sci Health B. 1988 Oct;23(5):513-24. PubMed PMID: 3209817.

15: Wiaderkiewicz R, Walter Z, Reimschussel W. Sites of methylation of DNA bases by the action of organophosphorus insecticides in vitro. Acta Biochim Pol. 1986;33(2):73-85. PubMed PMID: 3766014.

16: Beranek DT, Heflich RH, Kodell RL, Morris SM, Casciano DA. Correlation between specific DNA-methylation products and mutation induction at the HGPRT locus in Chinese hamster ovary cells. Mutat Res. 1983 Jun-Jul;110(1):171-80. PubMed PMID: 6865996.

17: Thomas L, Yang CH, Goldthwait DA. Two DNA glycosylases in Escherichia coli which release primarily 3-methyladenine. Biochemistry. 1982 Mar 16;21(6):1162-9. PubMed PMID: 7041972.

18: Bogden JM, Eastman A, Bresnick E. A system in mouse liver for the repair of O6-methylguanine lesions in methylated DNA. Nucleic Acids Res. 1981 Jul 10;9(13):3089-103. PubMed PMID: 7279663; PubMed Central PMCID: PMC327333.

19: Bennett RA, Pegg AE. Alkylation of DNA in rat tissues following administration of streptozotocin. Cancer Res. 1981 Jul;41(7):2786-90. PubMed PMID: 6454479.

20: Shackleton J, Warren W, Roberts JJ. The excision of N-methyl-N-nitrosourea-induced lesions from the DNA of Chinese hamster cells as measured by the loss of sites sensitive to an enzyme extract that excises 3-methylpurines but not O6-methylguanine. Eur J Biochem. 1979 Jul;97(2):425-33. PubMed PMID: 467426.