1-METHYLXANTHINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H6N4O2
Molecular Weight	166.1374
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(=O)NC2=C(NC=N2)C1=O

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

Approval Year

PubMed

Title	Date	PubMed
Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.	1995 Nov 9	7503772
Neurotoxic convulsions induced by theophylline and its metabolites in mice.	1996 Jun	8799489
The effect of pregnancy on cytochrome P4501A2, xanthine oxidase, and N-acetyltransferase activities in humans.	2001 Aug	11503005
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	11499474
Urinary biomarkers for assessing dietary exposure to caffeine.	2001 Dec	11761118
Physiologic hyperinsulinemia enhances human skeletal muscle perfusion by capillary recruitment.	2001 Dec	11723050
Caffeine metabolism before and after liver transplantation.	2001 Feb	11270802
Determination of urinary methylated purine pattern by high-performance liquid chromatography.	2001 Feb 10	11232859
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.	2001 Jan	11204934
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline.	2001 Mar	11465391
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	12542900
Skeletal muscle microvascular recruitment by physiological hyperinsulinemia precedes increases in total blood flow.	2002 Jan	11756321
T-1032, a cyclic GMP phosphodiesterase-5 inhibitor, acutely blocks physiologic insulin-mediated muscle haemodynamic effects and glucose uptake in vivo.	2003 Dec	14581178
Interaction of ibuprofen and probenecid with drug metabolizing enzyme phenotyping procedures using caffeine as the probe drug.	2003 Feb	12580991
Pharmacokinetics of intravenous theophylline in mutant Nagase analbuminemic rats.	2003 Jan 31	12570924
Inhibiting NOS blocks microvascular recruitment and blunts muscle glucose uptake in response to insulin.	2003 Jul	12791603
Preventive effect of zaprinast and 3-isobutyl, 1-methylxanthine (phosphodiesterase inhibitors) on gastric injury induced by nonsteroidal antiinflammatory drugs in rats.	2003 May	12772800
TNF-alpha acutely inhibits vascular effects of physiological but not high insulin or contraction.	2003 Sep	12759220
Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study.	2004	15217502
Cytochrome P450 1A2 (CYP1A2) activity, mammographic density, and oxidative stress: a cross-sectional study.	2004	15217501
Local methacholine but not bradykinin potentiates insulin-mediated glucose uptake in muscle in vivo by augmenting capillary recruitment.	2004 Dec	15602653
Insulin sensitivity of muscle capillary recruitment in vivo.	2004 Feb	14747297
Inhibition of the human organic anion transporter 1 by the caffeine metabolite 1-methylxanthine.	2004 Jul 16	15207706
Acetylator phenotyping in patients with malignant lymphomas, using caffeine as the metabolic probe.	2004 Jul-Aug	15520499
Phenotyping of N-acetyltransferase type 2 by caffeine from uncontrolled dietary exposure.	2004 Mar	14747882
High-throughput liquid chromatography-tandem mass spectrometry assay for plasma theophylline and its metabolites.	2004 Nov	15502093
Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples.	2004 Oct	15537072
Skeletal muscle contraction stimulates capillary recruitment and glucose uptake in insulin-resistant obese Zucker rats.	2004 Oct	15213062
Re-investigation of the concordance of human NAT2 phenotypes and genotypes.	2005 Apr	15558239
Measurement of caffeine and five of the major metabolites in urine by high-performance liquid chromatography/tandem mass spectrometry.	2005 Mar	15685651
Caffeine N3-demethylation (CYP1A2) in a population with an increased exposure to polychlorinated biphenyls.	2006 Dec	17089110
Effect of diet on the development of drug metabolism by cytochrome P-450 enzymes in healthy infants.	2006 Dec	17065585
[Determination of the activity of cytochrome P-450 CYP2A6 by HPLC method with caffeine as metabolizing probe].	2006 Mar	16759004
Reduction in non-glomerular renal clearance of the caffeine metabolite 1-methylxanthine by probenecid.	2007 Aug	17725176
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	17221922
Acute effects of wortmannin on insulin's hemodynamic and metabolic actions in vivo.	2007 Mar	17106063
Anti-inflammatory effect of theophylline in rats and its involvement of the glucocorticoid-glucocorticoid receptor system.	2008 Apr	18391482
Point: There is capillary recruitment in active skeletal muscle during exercise.	2008 Mar	17656624
Relaxing and contracting effects of theophylline's metabolites on the rabbit upper gastrointestinal tract.	2008 Oct	18844725
Enhancement of radiotherapeutic effectiveness by temperature-sensitive liposomal 1-methylxanthine.	2009 May 8	19167476
Demethylation of theophylline (1,3-dimethylxanthine) to 1-methylxanthine: the first step of an antioxidising cascade.	2010	20594417
Is 1-methylxanthine an ideal model substrate for establishing the renal tubular transport of organic ions?	2010 Feb	20137769
Plant polyphenol curcumin significantly affects CYP1A2 and CYP2A6 activity in healthy, male Chinese volunteers.	2010 Jun	20484172
Loss of insulin-mediated microvascular perfusion in skeletal muscle is associated with the development of insulin resistance.	2010 Sep	20649632

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