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

Molecular Formula	C6H6N4O2
Molecular Weight	166.1374
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Determination of urinary methylated purine pattern by high-performance liquid chromatography.	2001 Feb 10	11232859
Xanthine oxidase activity and blood glutathione redox ratio in infants and children with septic shock syndrome.	2001 Jan	11280638
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.	2001 Jan	11204934
[The acetylator polymorphism in a Khmer population: clinical consequences].	2001 Jul-Aug	11677864
Inhibition of human CYP1A2 activity in vitro by methylxanthines: potent competitive inhibition by 8-phenyltheophylline.	2001 Mar	11465391
Validity of an ELISA for N-acetyltransferase-2 (NAT2) phenotyping.	2001 May 1	11292476
Group I aptazymes as genetic regulatory switches.	2002 Dec 4	12466025
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
Inhibiting NOS blocks microvascular recruitment and blunts muscle glucose uptake in response to insulin.	2003 Jul	12791603
Nonnutritive flow impairs uptake of fatty acid by white muscles of the perfused rat hindlimb.	2003 Mar	12453824
Preventive effect of zaprinast and 3-isobutyl, 1-methylxanthine (phosphodiesterase inhibitors) on gastric injury induced by nonsteroidal antiinflammatory drugs in rats.	2003 May	12772800
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
Capillary electrochromatography of caffeine and its metabolites in rat brain microdialysate.	2005 Feb	15714566
Exercise and insulin-mediated capillary recruitment in muscle.	2005 Jan	15640720
Measurement of caffeine and five of the major metabolites in urine by high-performance liquid chromatography/tandem mass spectrometry.	2005 Mar	15685651
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	17991222
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
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	17011540
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
Phenotyping of N-acetyltransferase type 2 and xanthine oxidase with caffeine: when should urine samples be collected?	2009 Apr	19082994
1-Methylxanthine enhances the radiosensitivity of tumor cells.	2009 Feb	19280470
Caffeine metabolic ratios for the in vivo evaluation of CYP1A2, N-acetyltransferase 2, xanthine oxidase and CYP2A6 enzymatic activities.	2009 May	19519341
Enhancement of radiotherapeutic effectiveness by temperature-sensitive liposomal 1-methylxanthine.	2009 May 8	19167476

Substance Class	Chemical Created by `admin` on `Thu Jul 06 01:06:00 UTC 2023` Edited by `admin` on `Thu Jul 06 01:06:00 UTC 2023`
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