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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 of 1-METHYLXANTHINE

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

PubMed

TitleDatePubMed
Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.
1995 Nov 9
Neurotoxic convulsions induced by theophylline and its metabolites in mice.
1996 Jun
Physiologic hyperinsulinemia enhances human skeletal muscle perfusion by capillary recruitment.
2001 Dec
Exercise training improves insulin-mediated capillary recruitment in association with glucose uptake in rat hindlimb.
2001 Dec
Lipid infusion impairs physiologic insulin-mediated capillary recruitment and muscle glucose uptake in vivo.
2002 Apr
Severe 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) intoxication: insights into the measurement of hepatic cytochrome P450 1A2 induction.
2002 Aug
Skeletal muscle microvascular recruitment by physiological hyperinsulinemia precedes increases in total blood flow.
2002 Jan
T-1032, a cyclic GMP phosphodiesterase-5 inhibitor, acutely blocks physiologic insulin-mediated muscle haemodynamic effects and glucose uptake in vivo.
2003 Dec
Nonnutritive flow impairs uptake of fatty acid by white muscles of the perfused rat hindlimb.
2003 Mar
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
Insulin sensitivity of muscle capillary recruitment in vivo.
2004 Feb
Inhibition of the human organic anion transporter 1 by the caffeine metabolite 1-methylxanthine.
2004 Jul 16
Phenotyping of N-acetyltransferase type 2 by caffeine from uncontrolled dietary exposure.
2004 Mar
Skeletal muscle contraction stimulates capillary recruitment and glucose uptake in insulin-resistant obese Zucker rats.
2004 Oct
Capillary electrochromatography of caffeine and its metabolites in rat brain microdialysate.
2005 Feb
Caffeine N3-demethylation (CYP1A2) in a population with an increased exposure to polychlorinated biphenyls.
2006 Dec
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
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
Point: There is capillary recruitment in active skeletal muscle during exercise.
2008 Mar
Phenotyping of N-acetyltransferase type 2 and xanthine oxidase with caffeine: when should urine samples be collected?
2009 Apr
Demethylation of theophylline (1,3-dimethylxanthine) to 1-methylxanthine: the first step of an antioxidising cascade.
2010
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 Fri Dec 15 17:48:38 UTC 2023
Edited
by admin
on Fri Dec 15 17:48:38 UTC 2023
Record UNII
7EE8WCA32U
Record Status Validated (UNII)
Record Version
  • Download
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 Fri Dec 15 17:48:38 UTC 2023 , Edited by admin on Fri Dec 15 17:48:38 UTC 2023
PRIMARY
FDA UNII
7EE8WCA32U
Created by admin on Fri Dec 15 17:48:38 UTC 2023 , Edited by admin on Fri Dec 15 17:48:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID30210271
Created by admin on Fri Dec 15 17:48:38 UTC 2023 , Edited by admin on Fri Dec 15 17:48:38 UTC 2023
PRIMARY
PUBCHEM
80220
Created by admin on Fri Dec 15 17:48:38 UTC 2023 , Edited by admin on Fri Dec 15 17:48:38 UTC 2023
PRIMARY
CAS
6136-37-4
Created by admin on Fri Dec 15 17:48:38 UTC 2023 , Edited by admin on Fri Dec 15 17:48:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
228-108-5
Created by admin on Fri Dec 15 17:48:38 UTC 2023 , Edited by admin on Fri Dec 15 17:48:38 UTC 2023
PRIMARY
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