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666548

Sigma-Aldrich

7-Methyladenine

97%

Synonym(s):

6-Amino-7-methylpurine, 7-Methyl-7H-purin-6-amine

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About This Item

Empirical Formula (Hill Notation):
C6H7N5
CAS Number:
Molecular Weight:
149.15
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

form

solid

mp

346-350 °C

SMILES string

Cn1cnc2ncnc(N)c12

InChI

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

InChI key

HCGHYQLFMPXSDU-UHFFFAOYSA-N

Application

<ul>
<li><strong>Biomarkers of Cigarette Smoking and DNA Methylating Agents:</strong> Study on 7-Methyladenine highlights its role as a biomarker of DNA damage from exposure to methylating agents (Harroun et al., 2017).</li>
</ul>

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Sens. 1

Storage Class Code

11 - 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

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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H G Mandel et al.
Analytical biochemistry, 217(2), 292-297 (1994-03-01)
We have developed a procedure for isolating and quantifying 7-methyladenine from rat urine following the administration to the rat of methylating agents, such as dimethylnitrosamine. Urinary 7-methyladenine and its trideutero isomer, added as an internal standard, were precipitated with silver
B Tudek et al.
Acta biochimica Polonica, 46(3), 785-799 (2000-03-04)
The most abundant lesion formed in DNA upon modification with methylating agents 7-methylguanine, under alkaline conditions is converted into 2,6-diamino-4-hydroxy-5N-methyl-formamidopyrimidine (Fapy-7MeGua). We have previously shown that treatment of dimethylsulfate methylated DNA with NaOH creates mutagenic base derivatives leading to a
H G Mandel et al.
Carcinogenesis, 10(4), 757-762 (1989-04-01)
Relatively simple and rapid analytical procedures involving two sequential HPLC separations were developed for the isolation of methylated purines in the urine of rats administered radiolabeled methylating carcinogens. Following a dose of [3H]N-methyl-N-nitrosourea (MNU), 7-methyl-adenine (m7Gua) was detected by chromatography
H G Mandel et al.
Carcinogenesis, 15(7), 1393-1398 (1994-07-01)
Earlier studies showed that urine of rats which had been injected with the methylating agent N-[3H-methyl]-N-nitrosourea contained a previously undetected metabolic product, 7-[3H-methyl]adenine. This methylpurine, undoubtedly derived from alkylation of nucleic acids followed by depurination, was not labeled when 14C-methyl-labeled
Shinji Tokuda et al.
Bioscience, biotechnology, and biochemistry, 76(4), 828-830 (2012-04-10)
Adenine had a concentration-dependent relaxation action on the phenylephrine-contracted aorta ring, with an EC(50) value of 0.40±0.12 mM. This effect was also observed in the endothelium-denuded aorta. Among the adenine analogues, N-methyladenine and benzimidazole still evoked an apparent relaxation effect

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