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Details

Stereochemistry ACHIRAL
Molecular Formula C6H6N4O2
Molecular Weight 166.1377
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 1-METHYLXANTHINE

SMILES

Cn1c(=O)c2c([nH]cn2)nc1O

InChI

InChIKey=MVOYJPOZRLFTCP-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C6H6N4O2
Molecular Weight 166.1377
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Neurotoxic convulsions induced by theophylline and its metabolites in mice.
1996 Jun
The effect of pregnancy on cytochrome P4501A2, xanthine oxidase, and N-acetyltransferase activities in humans.
2001 Aug
Use of novel solid-phase extraction sorbent materials for high-performance liquid chromatography quantitation of caffeine metabolism products methylxanthines and methyluric acids in samples of biological origin.
2001 Aug 15
Urinary biomarkers for assessing dietary exposure to caffeine.
2001 Dec
Exercise training improves insulin-mediated capillary recruitment in association with glucose uptake in rat hindlimb.
2001 Dec
Caffeine metabolism before and after liver transplantation.
2001 Feb
Xanthine oxidase activity and blood glutathione redox ratio in infants and children with septic shock syndrome.
2001 Jan
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.
2001 Jan
[The acetylator polymorphism in a Khmer population: clinical consequences].
2001 Jul-Aug
Validity of an ELISA for N-acetyltransferase-2 (NAT2) phenotyping.
2001 May 1
Severe 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) intoxication: insights into the measurement of hepatic cytochrome P450 1A2 induction.
2002 Aug
Effects of acute renal failure induced by uranyl nitrate on the pharmacokinetics of intravenous theophylline in rats: the role of CYP2E1 induction in 1,3-dimethyluric acid formation.
2002 Dec
Insulin-mediated hemodynamic changes are impaired in muscle of Zucker obese rats.
2002 Dec
Group I aptazymes as genetic regulatory switches.
2002 Dec 4
Skeletal muscle microvascular recruitment by physiological hyperinsulinemia precedes increases in total blood flow.
2002 Jan
Interaction of ibuprofen and probenecid with drug metabolizing enzyme phenotyping procedures using caffeine as the probe drug.
2003 Feb
Pharmacokinetics of intravenous theophylline in mutant Nagase analbuminemic rats.
2003 Jan 31
Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study.
2004
Cytochrome P450 1A2 (CYP1A2) activity, mammographic density, and oxidative stress: a cross-sectional study.
2004
Local methacholine but not bradykinin potentiates insulin-mediated glucose uptake in muscle in vivo by augmenting capillary recruitment.
2004 Dec
Acetylator phenotyping in patients with malignant lymphomas, using caffeine as the metabolic probe.
2004 Jul-Aug
Phenotyping of N-acetyltransferase type 2 by caffeine from uncontrolled dietary exposure.
2004 Mar
High-throughput liquid chromatography-tandem mass spectrometry assay for plasma theophylline and its metabolites.
2004 Nov
Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples.
2004 Oct
Skeletal muscle contraction stimulates capillary recruitment and glucose uptake in insulin-resistant obese Zucker rats.
2004 Oct
Re-investigation of the concordance of human NAT2 phenotypes and genotypes.
2005 Apr
Capillary electrochromatography of caffeine and its metabolites in rat brain microdialysate.
2005 Feb
Measurement of caffeine and five of the major metabolites in urine by high-performance liquid chromatography/tandem mass spectrometry.
2005 Mar
Associations between CYP2E1 promoter polymorphisms and plasma 1,3-dimethyluric acid/theophylline ratios.
2006 Aug
Caffeine N3-demethylation (CYP1A2) in a population with an increased exposure to polychlorinated biphenyls.
2006 Dec
Effect of diet on the development of drug metabolism by cytochrome P-450 enzymes in healthy infants.
2006 Dec
[Determination of the activity of cytochrome P-450 CYP2A6 by HPLC method with caffeine as metabolizing probe].
2006 Mar
Caffeine metabolites are inhibitors of the nuclear enzyme poly(ADP-ribose)polymerase-1 at physiological concentrations.
2006 Sep 28
Theophylline and its metabolites produce a stimulating cholinergic effect on the small intestine and a nonadrenergic noncholinergic relaxing effect on the colon: a comparative study in the rabbit intestine.
2007 Dec
In vivo evaluation of CYP1A2, CYP2A6, NAT-2 and xanthine oxidase activities in a Greek population sample by the RP-HPLC monitoring of caffeine metabolic ratios.
2007 Feb
Concordance between the deduced acetylation status generated by high-speed: real-time PCR based NAT2 genotyping of seven single nucleotide polymorphisms and human NAT2 phenotypes determined by a caffeine assay.
2007 Feb
Acute effects of wortmannin on insulin's hemodynamic and metabolic actions in vivo.
2007 Mar
Inhibitory effects of caffeine and its metabolites on intracellular lipid accumulation in murine 3T3-L1 adipocytes.
2008
Anti-inflammatory effect of theophylline in rats and its involvement of the glucocorticoid-glucocorticoid receptor system.
2008 Apr
Point: There is capillary recruitment in active skeletal muscle during exercise.
2008 Mar
Relaxing and contracting effects of theophylline's metabolites on the rabbit upper gastrointestinal tract.
2008 Oct
Simultaneous action of the flavonoid quercetin on cytochrome P450 (CYP) 1A2, CYP2A6, N-acetyltransferase and xanthine oxidase activity in healthy volunteers.
2009 Aug
Caffeine metabolic ratios for the in vivo evaluation of CYP1A2, N-acetyltransferase 2, xanthine oxidase and CYP2A6 enzymatic activities.
2009 May
Interleukin-6 attenuates insulin-mediated increases in endothelial cell signaling but augments skeletal muscle insulin action via differential effects on tumor necrosis factor-alpha expression.
2009 May
Enhancement of radiotherapeutic effectiveness by temperature-sensitive liposomal 1-methylxanthine.
2009 May 8
Loss of insulin-mediated microvascular perfusion in skeletal muscle is associated with the development of insulin resistance.
2010 Sep
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:48:56 UTC 2021
Edited
by admin
on Sat Jun 26 07:48:56 UTC 2021
Record UNII
7EE8WCA32U
Record Status Validated (UNII)
Record Version
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Name Type Language
1-METHYLXANTHINE
Systematic Name English
XANTHINE, 1-METHYL-
Systematic Name English
1H-PURINE-2,6-DIONE, 3,7-DIHYDRO-1-METHYL-
Systematic Name English
1H-PURINE-2,6-DIONE, 3,9-DIHYDRO-1-METHYL-
Systematic Name English
Code System Code Type Description
MESH
C053085
Created by admin on Sat Jun 26 07:48:57 UTC 2021 , Edited by admin on Sat Jun 26 07:48:57 UTC 2021
PRIMARY
FDA UNII
7EE8WCA32U
Created by admin on Sat Jun 26 07:48:57 UTC 2021 , Edited by admin on Sat Jun 26 07:48:57 UTC 2021
PRIMARY
EPA CompTox
6136-37-4
Created by admin on Sat Jun 26 07:48:57 UTC 2021 , Edited by admin on Sat Jun 26 07:48:57 UTC 2021
PRIMARY
PUBCHEM
80220
Created by admin on Sat Jun 26 07:48:57 UTC 2021 , Edited by admin on Sat Jun 26 07:48:57 UTC 2021
PRIMARY
CAS
6136-37-4
Created by admin on Sat Jun 26 07:48:57 UTC 2021 , Edited by admin on Sat Jun 26 07:48:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
228-108-5
Created by admin on Sat Jun 26 07:48:57 UTC 2021 , Edited by admin on Sat Jun 26 07:48:57 UTC 2021
PRIMARY
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URINE