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M6885

Sigma-Aldrich

1-Methyluric acid

Synonym(s):

1-Methyl-2,6,8-trihydroxypurine, 1-U, 1MUA

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About This Item

Empirical Formula (Hill Notation):
C6H6N4O3
CAS Number:
708-79-2
Molecular Weight:
182.14
Beilstein:
195190
EC Number:
211-905-7
MDL number:
MFCD00042987
UNSPSC Code:
41106305
PubChem Substance ID:
24897125
NACRES:
NA.51

Assay

≥98% (HPLC)

form

powder

solubility

1 M NaOH: 20 mg/mL, clear to slightly hazy

SMILES string

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

InChI

1S/C6H6N4O3/c1-10-4(11)2-3(9-6(10)13)8-5(12)7-2/h1H3,(H,9,13)(H2,7,8,12)

InChI key

QFDRTQONISXGJA-UHFFFAOYSA-N

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Application

1-Methyluric acid has been used:
  • for the determination of uric acid in stool samples by liquid chromatography and tandem mass spectrometry
  • in turbidimetric assay of synthetic urine samples
  • as a substrate for CYP1A2(cytochrome P450 family 1 subfamily A member 2) assay

Biochem/physiol Actions

1-Methyluric acid (1-U) is a major metabolite of caffeine and theophylline with antioxidant activity that protects molecules such as low density lipoproteins (LDL) from oxidative modifications. 1-Methyluric acid may be used in studies aimed at differentiating the activities of caffeine and theophylline metabolites.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Effects of peppermint tea consumption on the activities of CYP1A2, CYP2A6, Xanthine Oxidase, N-acetyltranferase-2 and UDP-glucuronosyltransferases-1A1/1A6 in healthy volunteers
Begas E, et al.
Food And Chemical Toxicology, 100, 80-89 (2017)
C Lee
Clinica chimica acta; international journal of clinical chemistry, 295(1-2), 141-154 (2000-04-18)
Although caffeine has been suggested as an antioxidant at millimolar concentrations, little information is available about the antioxidant activity of caffeine and its metabolites at physiological concentrations. Antioxidant activity was measured by oxygen-radical absorbing capacity (ORAC) using 2, 2'-azobis(2-amidinopropane) dihydrochloride
Theophano A Psarra et al.
Fundamental & clinical pharmacology, 22(5), 537-547 (2008-10-11)
The present study, aimed to clarify whether the gastrointestinal adverse effects following administration of the bronchodilator theophylline are owing to the action of the drug itself or its metabolites, investigates the pharmacodymanic effects of theophylline's metabolites on the spontaneous contractility
Xanthine urolithiasis: Inhibitors of xanthine crystallization
Grases F, et al.
bioRxiv, 335364-335364 (2018)
Klaus Abraham et al.
Clinical pharmacology and therapeutics, 72(2), 163-174 (2002-08-22)
The correct in vivo quantification of aryl hydrocarbon receptor-mediated induction of cytochrome P450 1A2 (CYP1A2) in humans is a long-standing question. We compared the performance of several modifications of the caffeine test for measurement of CYP1A2 activity in subjects with
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