280984

Sigma-Aldrich

1-Methylxanthine

98%

Synonym(s):
2,6-Dihydroxy-1-methylpurine
Empirical Formula (Hill Notation):
C6H6N4O2
CAS Number:
Molecular Weight:
166.14
Beilstein/REAXYS Number:
171507
EC Number:
MDL number:
PubChem Substance ID:

assay

98%

mp

≥300 °C

SMILES string

CN1C(=O)Nc2nc[nH]c2C1=O

InChI

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

InChI key

MVOYJPOZRLFTCP-UHFFFAOYSA-N

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Features and Benefits

Caffeine metabolite.

Certificate of Analysis

Certificate of Origin

P St-Pierre et al.
Diabetes, obesity & metabolism, 14(8), 753-761 (2012-03-21)
Exercise and insulin each increase microvascular blood flow and enhance glucose disposal in skeletal muscle. We have reported that insulin-mediated microvascular recruitment in a diet-induced model of insulin resistance (high-fat feeding for 4 weeks) is markedly impaired; however, the effect...
Hyewon Youn et al.
International journal of radiation biology, 85(2), 167-174 (2009-03-13)
To determine the efficacy of a caffeine derivative 1-methylxanthine (1-MTX) in increasing radiosensitivity of cancer cells and elucidate the underlying mechanisms in vitro. RKO human colorectal cancer cells carrying wild type protein 53 kDa (p53) were incubated with 3 mM...
Stephen Rattigan et al.
Exercise and sport sciences reviews, 33(1), 43-48 (2005-01-11)
Blood flow to contracting muscles is increased rapidly and is redistributed within the muscle. Recent research has highlighted that insulin causes similar changes, but these are absent in insulin resistance, resulting in impaired insulin-mediated muscle glucose uptake. Understanding the mechanisms...
Catherine M Wheatley et al.
American journal of physiology. Endocrinology and metabolism, 287(4), E804-E809 (2004-06-24)
Exercise and insulin increase muscle glucose uptake by different mechanisms and also increase capillary recruitment, which is proposed to facilitate access for hormones and nutrients. The genetically obese Zucker rat shows impaired insulin- but not contraction-mediated glucose uptake in muscle....
Seong-Yun Jeong et al.
International journal of pharmaceutics, 372(1-2), 132-139 (2009-01-27)
Most of methylxanthine derivatives including caffeine have been known to radiosensitize cancer cells, but the obstacles such as toxicity, request of high dose and poor solubility hinder their preclinical evaluations and clinical applications. In this study, we evaluated the efficacy...

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