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69723

Sigma-Aldrich

7-Methylxanthine

≥98.0% (HPLC)

Synonym(s):

2,6-Dihydroxy-7-methylpurine, Heteroxanthine

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About This Item

Empirical Formula (Hill Notation):
C6H6N4O2
CAS Number:
552-62-5
Molecular Weight:
166.14
Beilstein/REAXYS Number:
171027
EC Number:
209-019-0
MDL number:
MFCD00037979
UNSPSC Code:
12352005
PubChem Substance ID:
57652205
NACRES:
NA.22

assay

≥98.0% (HPLC)

form

powder

mp

≥300 °C

SMILES string

Cn1cnc2NC(=O)NC(=O)c12

InChI

1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)

InChI key

PFWLFWPASULGAN-UHFFFAOYSA-N

Gene Information

rat ... Adora1(29290) , Adora2a(25369)

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General description

7-Methylxanthine is an oxopurine, which belongs to the class of xanthines. It may be synthesized by the reaction between 4-amino-1-methylimidazole-5-carboxamide and diethyl carbonate.

Application

7-Methylxanthine can be used as a building block to synthesize tricyclic imidazo[2,1-i]purinone derivatives as potential adenosine receptor antagonists.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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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Kouichi Mizuno et al.
FEBS letters, 534(1-3), 75-81 (2003-01-16)
In coffee and tea plants, caffeine is synthesized from xanthosine via a pathway that includes three methylation steps. We report the isolation of a bifunctional coffee caffeine synthase (CCS1) clone from coffee endosperm by reverse transcription-polymerase chain reaction (RT-PCR) and
Dongmei Cui et al.
Acta ophthalmologica, 89(4), 328-334 (2009-10-29)
The aim of this study was to determine the effect of the adenosine receptor antagonist 7-methylxanthine (7-MX) on form deprivation myopia in 3-week-old guinea pigs. Two groups of 3-week-old guinea pigs were subjected to monocular deprivation (MD) using a diffuser
K Trier et al.
The British journal of ophthalmology, 83(12), 1370-1375 (1999-11-27)
To examine a possible effect of 7-methylxanthine, theobromine, acetazolamide, or L-ornithine on the ultrastructure and biochemical composition of rabbit sclera. Groups of pigmented rabbits, six in each group, were dosed during 10 weeks with one of the substances under investigation
Swati Sucharita Dash et al.
Current microbiology, 55(1), 56-60 (2007-06-08)
In this study, the kinetics of degradation of caffeine and related methylxanthines by induced cells of Pseudomonas sp. was performed. The kinetics data showed that degradation of caffeine, theobromine, and 7-methylxanthine followed Michealis-Menten kinetics. The values of K (m) are
H M Himmel et al.
Journal of chromatography, 568(1), 105-115 (1991-07-17)
A high-performance liquid chromatographic method is described for the separation and quantitation of several purine compounds, including hypoxanthine. The isocratic separation of a standard mixture of nine compounds is achieved within 20 min on a reversed-phase Nucleosil 100-5C18 column, with
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Articles

HPLC Analysis of Xanthines on Purospher® STAR RP-18 endcapped

Xanthine is a purine base found in most human body tissues and fluids as well as in other organisms. Methylated xanthines (methylxanthines), which include caffeine, paraxanthine, theobromine, and theophylline, commonly used for their effects as mild stiµlants and as bronchodilators, notably in the treatment of asthma symptoms. This application shows the efficient separation of several common xanthines and may be applied their analysis in any number of desired matrices.

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