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7-methyl xanthine
heteroxanthin

Supplier Sponsors

Name:7-methyl-3H-purine-2,6-dione
CAS Number: 552-62-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:209-019-0
FDA UNII: E9M81NJM6G
Nikkaji Web:J1.614D
Beilstein Number:0171027
MDL:MFCD00037979
XlogP3:-0.90 (est)
Molecular Weight:166.14022000
Formula:C6 H6 N4 O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 1.807e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
7-Methylxanthine 95%
Santa Cruz Biotechnology
For experimental / research use only.
7-Methylxanthine 98%
Sigma-Aldrich: Aldrich
For experimental / research use only.
7-Methylxanthine ≥98.0% (HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for 7-methyl xanthine usage levels up to:
 not for fragrance use.
 
Recommendation for 7-methyl xanthine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :68374
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
7-methyl-3H-purine-2,6-dione
Chemidplus:0000552625
RTECS:ZD8925000 for cas# 552-62-5
 
References:
 7-methyl-3H-purine-2,6-dione
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):68374
Pubchem (cas):552-62-5
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
UM BBD:Search
KEGG (GenomeNet):C16353
HMDB (The Human Metabolome Database):HMDB01991
FooDB:FDB001978
Export Tariff Code:2933.90.9500
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 coffee
Search Trop Picture
 sugar cane
Search Picture
 
Synonyms:
3,7-dihydro-7-methyl-1H-purine-2,6-dione
 heteroxanthin
7-methyl-3H-purine-2,6-dione
7-methylxanthine
1H-purine-2,6-dione, 3,7-dihydro-7-methyl-
 xanthine, 7-methyl-
 

Articles:

PubMed:Dataset on exogenous application of salicylic acid and methyljasmonate and the accumulation of caffeine in young leaf tissues and catabolically inactive endosperms.
PubMed:Engineering a microbial platform for de novo biosynthesis of diverse methylxanthines.
PubMed:Exploration of Biomarkers for Amoxicillin/Clavulanate-Induced Liver Injury: Multi-Omics Approaches.
PubMed:Production of Recombinant Caffeine Synthase from Guarana (Paullinia cupana var. sorbilis) in Escherichia coli.
PubMed:Theoretical study on the N-demethylation mechanism of theobromine catalyzed by P450 isoenzyme 1A2.
PubMed:Levels of caffeine and its metabolites among U.S. smokers and nonsmokers.
PubMed:Wastewater analysis to monitor use of caffeine and nicotine and evaluation of their metabolites as biomarkers for population size assessment.
PubMed:Molecular and biochemical characterization of caffeine synthase and purine alkaloid concentration in guarana fruit.
PubMed:Quantum mechanical/molecular mechanical study of catalytic mechanism and role of key residues in methylation reactions catalyzed by dimethylxanthine methyltransferase in caffeine biosynthesis.
PubMed:The role of the adenosinergic system in lung fibrosis.
PubMed:Caffeine junkie: an unprecedented glutathione S-transferase-dependent oxygenase required for caffeine degradation by Pseudomonas putida CBB5.
PubMed:Effects of 7-methylxanthine on form-deprivation myopia in pigmented rabbits.
PubMed:Novel, highly specific N-demethylases enable bacteria to live on caffeine and related purine alkaloids.
PubMed:Characterization of a broad-specificity non-haem iron N-demethylase from Pseudomonas putida CBB5 capable of utilizing several purine alkaloids as sole carbon and nitrogen source.
PubMed:Distribution, biosynthesis and catabolism of methylxanthines in plants.
PubMed:Extracellular 3',5'-cAMP-adenosine pathway inhibits glomerular mesangial cell growth.
PubMed:Systemic 7-methylxanthine in retarding axial eye growth and myopia progression: a 36-month pilot study.
PubMed:Effects of 7-methylxanthine on the sclera in form deprivation myopia in guinea pigs.
PubMed:Synthesis and pharmacological evaluation of novel 1- and 8-substituted-3-furfuryl xanthines as adenosine receptor antagonists.
PubMed:Adenosine receptor protein changes in guinea pigs with form deprivation myopia.
PubMed:Two distinct pathways for metabolism of theophylline and caffeine are coexpressed in Pseudomonas putida CBB5.
PubMed:Non-standard base pairing and stacked structures in methyl xanthine clusters.
PubMed:Caffeine and related purine alkaloids: biosynthesis, catabolism, function and genetic engineering.
PubMed:Dimerization of N-methyltransferases involved in caffeine biosynthesis.
PubMed:Degradation kinetics of caffeine and related methylxanthines by induced cells of Pseudomonas sp.
PubMed:Differential effect of selected methylxanthine derivatives on radiosensitization of lung carcinoma cells.
PubMed:Interactions between metabotropic glutamate 5 and adenosine A2A receptors in normal and parkinsonian mice.
PubMed:Caffeine production in tobacco plants by simultaneous expression of three coffee N-methyltrasferases and its potential as a pest repellant.
PubMed:Methylated purines in urinary stones.
PubMed:Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection.
PubMed:Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples.
PubMed:Acid-base properties of xanthosine 5'-monophosphate (XMP) and of some related nucleobase derivatives in aqueous solution: micro acidity constant evaluations of the (N1)H versus the (N3)H deprotonation ambiguity.
PubMed:Adenosine A(2a) receptor antagonists: potential therapeutic and neuroprotective effects in Parkinson's disease.
PubMed:Caffeine synthase and related methyltransferases in plants.
PubMed:The first committed step reaction of caffeine biosynthesis: 7-methylxanthosine synthase is closely homologous to caffeine synthases in coffee (Coffea arabica L.).
PubMed:Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants.
PubMed:Inhibition of monoamine oxidase B by selective adenosine A2A receptor antagonists.
PubMed:[Research on the separation of caffeine and its nine analogues by micellar electrokinetic capillary chromatography].
PubMed:Isolation of a new dual-functional caffeine synthase gene encoding an enzyme for the conversion of 7-methylxanthine to caffeine from coffee (Coffea arabica L.).
PubMed:Identification of N1-methyl-2-pyridone-5-carboxamide and N1-methyl-4-pyridone-5-carboxamide as components in urine extracts of individuals consuming coffee.
PubMed:Stimulatory effects of adenosine on prolactin secretion in the pituitary gland of the rat.
PubMed:Differences in caffeine and paraxanthine metabolism between human and murine CYP1A2.
PubMed:[Identification and quantitation of purine derivatives in urinary calculi as markers of abnormal purine metabolism by using high-performance liquid chromatography (HPLC)].
PubMed: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.
PubMed:A new caffeine biosynthetic pathway in tea leaves: utilisation of adenosine released from the S-adenosyl-L-methionine cycle.
PubMed:Selective adenosine A2A receptor antagonists.
PubMed:Adenosine A(2A) receptor enhances GABA(A)-mediated IPSCs in the rat globus pallidus.
PubMed:Caffeine metabolism before and after liver transplantation.
PubMed:Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.
PubMed:7-Methylxanthine methyltransferase of coffee plants. Gene isolation and enzymatic properties.
PubMed:Relationship between the severity of alcoholic liver cirrhosis and the metabolism of caffeine in 226 patients.
PubMed:Characterization of purine receptors in fetal lamb pulmonary circulation.
PubMed:Biochemical and ultrastructural changes in rabbit sclera after treatment with 7-methylxanthine, theobromine, acetazolamide, or L-ornithine.
PubMed:Purification and characterization of caffeine synthase from tea leaves.
PubMed:Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism.
PubMed:Pharmacological characterization of a simple behavioral response mediated selectively by central adenosine A1 receptors, using in vivo and in vitro techniques.
PubMed:A study on the route of 1-methylurate formation in theophylline metabolism.
PubMed:Nerve growth factor (NGF) expression in rat microglia is induced by adenosine A2a-receptors.
PubMed:Endogenous adenosine facilitates neurotransmission via A2A adenosine receptors in the rat superior colliculus in vivo.
PubMed:In vivo biodistribution of [N-11C-methyl]KF 17837 using 3-D-PET: evaluation as a ligand for the study of adenosine A2A receptors.
PubMed:Propentofylline inhibits polymorphonuclear leukocyte recruitment in vivo by a mechanism involving adenosine A2A receptors.
PubMed:Cyclooxygenase-2 expression in rat microglia is induced by adenosine A2a-receptors.
PubMed:Adenosine A2A receptors mediate the inhibitory effect of adenosine on formyl-Met-Leu-Phe-stimulated respiratory burst in neutrophil leucocytes.
PubMed:Biosynthesis of Caffeine in Leaves of Coffee.
PubMed:Elimination of theobromine metabolites in healthy adults.
PubMed:Adenosine A2a receptor-mediated modulation of striatal acetylcholine release in vivo.
PubMed:Adenosine A2b receptors mediate an increase in interleukin (IL)-6 mRNA and IL-6 protein synthesis in human astroglioma cells.
PubMed:A1, but not A2A, adenosine receptors modulate electrically stimulated [14C]acetylcholine release from rat cortex.
PubMed:Degradation of caffeine and related methylxanthines bySerratia marcescens isolated from soil under coffee cultivation.
PubMed:GTP and guanosine synergistically enhance NGF-induced neurite outgrowth from PC12 cells.
PubMed:Activation of adenosine A2 receptors stimulates phosphoinositide metabolism in rat peripheral nerve.
PubMed:The role of adenosine A2a receptors in regulating GABAergic synaptic transmission in striatal medium spiny neurons.
PubMed:Differential vasodilatory action of 2-octynyladenosine (YT-146), an adenosine A2 receptor agonist, in the isolated rat femoral artery and vein.
PubMed:Aminophylline enhances resting Ca2+ concentrations and twitch tension by adenosine receptor blockade in Rana pipiens.
PubMed:Evidence for P2-purinoceptor-mediated inhibition of noradrenaline release in rat brain cortex.
PubMed:Inhibition by KF17837 of adenosine A2A receptor-mediated modulation of striatal GABA and ACh release.
PubMed:Determination of caffeine and its metabolites in urine by high-performance liquid chromatography and capillary electrophoresis.
PubMed:Stimulation of reactive astrogliosis in vivo by extracellular adenosine diphosphate or an adenosine A2 receptor agonist.
PubMed:KF17837 ((E)-8-(3,4-dimethoxystyryl)-1,3-dipropyl-7-methylxanthine), a potent and selective adenosine A2 receptor antagonist.
PubMed:Photoisomerization of a potent and selective adenosine A2 antagonist, (E)-1,3-Dipropyl-8-(3,4-dimethoxystyryl)-7-methylxanthine.
PubMed:Microcirculatory responses to adenosine in the newborn pig retina.
PubMed:Adenosine modulates reactive hyperemia in rat gut.
PubMed:Adenosine receptor-blocking xanthines as inhibitors of phosphodiesterase isozymes.
PubMed:Protection against acute MPTP-induced dopamine depletion in mice by adenosine A1 agonist.
PubMed:Locomotor activity in mice during chronic treatment with caffeine and withdrawal.
PubMed:Effect of adenosine analogues on plasma corticosterone concentration in rats.
PubMed:Purine nucleosides and nucleotides stimulate proliferation of a wide range of cell types.
PubMed:Biosynthesis of Caffeine from Purine Nucleotides in Tea Plant.
PubMed:Hypothermic effects of alkylxanthines: evidence for a calcium-independent phosphodiesterase action.
PubMed:Quantitation of hypoxanthine in plasma from patients with ischemic heart disease: adaption of a high-performance liquid chromatographic method.
PubMed:Caffeine acetylator phenotyping during maturation in infants.
PubMed:Gas chromatographic-mass spectrometric quantitation of tri-, di- and monomethylxanthines and uric acids from hepatocyte incubation media.
PubMed:Adenosine and related compounds counteract tumor necrosis factor-alpha inhibition of neutrophil migration: implication of a novel cyclic AMP-independent action on the cell surface.
PubMed:Human N-acetylation genotype determination with urinary caffeine metabolites.
PubMed:Adenosine and its analogs stimulate phosphoinositide hydrolysis in the kidney.
PubMed:Nuclear incorporation of [adenine 14C]NAD is altered by compounds which affect poly(ADP-ribose) formation.
PubMed:Effects of 8-phenyl and 8-cycloalkyl substituents on the activity of mono-, di-, and trisubstituted alkylxanthines with substitution at the 1-, 3-, and 7-positions.
PubMed:Paraxanthine metabolism in humans: determination of metabolic partial clearances and effects of allopurinol and cimetidine.
PubMed:Determination of 7-methylguanine by immunoassay.
PubMed:Reactions of theophylline, theobromine and caffeine with Fenton's reagent--simulation of hepatic metabolism.
PubMed:In vivo and in vitro 1-methylxanthine metabolism in the rat. Evidence that the dehydrogenase form of xanthine oxidase predominates in intact perfused liver.
PubMed:In vivo and in vitro biotransformation of theobromine by phenobarbital- and 3-methylcholanthrene-inducible cytochrome P-450 monooxygenases in rat liver. Role of thiol compounds.
PubMed:Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors.
PubMed:Diet-induced alterations in theobromine disposition and toxicity in the rat.
PubMed:The mechanism of caffeine-enhanced glucose stimulation of liver glycogen synthase phosphatase activity.
PubMed:Metabolism, distribution, seminal excretion and pharmacokinetics of caffeine in the rabbit.
PubMed:High levels of methylxanthines in chocolate do not alter theobromine disposition.
PubMed:Pharmacokinetics of theobromine and its metabolites in rabbits.
PubMed:Antagonism of the behavioral effects of L-phenylisopropyladenosine (L-PIA) by caffeine and its metabolites.
PubMed:Kinetics and metabolism of theobromine in male and female non-pregnant and pregnant rabbits.
PubMed:Comparative theobromine metabolism in five mammalian species.
PubMed:Theobromine kinetics and metabolic disposition.
PubMed:Theobromine metabolism and pharmacokinetics in pregnant and nonpregnant Sprague-Dawley rats.
PubMed:N-methyltransferase activities in suspension cultures of Coffea arabica L.
PubMed:Theobromine metabolism in man.
PubMed:The metabolism of caffeine by a Pseudomonas putida strain.
PubMed:Simultaneous assay of the methylxanthine metabolites of caffeine in plasma by high performance liquid chromatography.
PubMed:Metabolism of methionine and biosynthesis of caffeine in the tea plant (Camellia sinensis L.).
PubMed:Complexes of poly(adenylic acid) with complementary monomers.
PubMed:The effect of methylxanthines on chromosomes of human lyphocytes in culture.
PubMed:Urinary purine levels in suicide.
PubMed:Biosynthesis of caffeine by tea-leaf extracts. Enzymic formation of theobromine from 7-methylxanthine and of caffeine from theobromine.
PubMed:[A new method for the synthesis of theobromine, caffeine and 7-methylxanthine].
 
Notes:
Found in sugar cane and other biol. sources, a urinary metab. of caffeine in man 7-Methylxanthine is a methyl derivative of xanthine, found occasionally in human urine. 7-Methylxanthine is one of the purine components in urinary calculi. Methylated purines originate from the metabolism of methylxanthines (caffeine, theophylline and theobromine. Purine derivatives in urinary calculi could be considered markers of abnormal purine metabolism. The content of a purine derivative in stone depends on its average urinary excretion in the general population, similarity to the chemical structure of uric acid, and content of the latter in stone. This suggests that purines in stones represent a solid solution with uric acid as solvent. It is also plausible that methylxanthines, ubiquitous components of the diet and drugs, are involved in the pathogenesis of urolithiasis. Caffeine is metabolized via successive pathways mainly catalyzed by CYP1A2, xanthine oxidase or N-acetyltransferase-2 to give 14 different metabolites. CYP1A2 activity shows an inter-individual variability among the population. CYP1A2, an isoform of the CYP1A cytochrome P450 super-family, is involved in the metabolism of many drugs and plays a potentially important role in the induction of chemical carcinogenesis. (PMID: 11712316, 15833286, 3506820, 15013152); Xanthine (pronounced /?zŠn?i?n, ?zŠn?a?n]/), (3,7-dihydro-purine-2,6-dione), is a purine base found in most body tissues and fluids and in other organisms. A number of mild stimulants are derived from xanthine, including caffeine and theobromine.; Xanthine is a product on the pathway of purine degradation.
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