3-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

CN1C2=C(N=CN2)C(=O)NC1=O

InChI

InChIKey=GMSNIKWWOQHZGF-UHFFFAOYSA-N

InChI=1S/C6H6N4O2/c1-10-4-3(7-2-8-4)5(11)9-6(10)12/h2H,1H3,(H,7,8)(H,9,11,12)

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16870158 | https://www.ncbi.nlm.nih.gov/pubmed/16678550

3-Methylxanthine is a metabolite of caffeine and theophylline.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Ultrafast dynamics show that the theophylline and 3-methylxanthine aptamers employ a conformational capture mechanism for binding their ligands.	2010-04-06	20214401
Demethylation of theophylline (1,3-dimethylxanthine) to 1-methylxanthine: the first step of an antioxidising cascade.	2010	20594417
A simple HPLC method for the quantification of mizoribine in human serum: pharmacokinetic applications.	2008-11	18661478
Relaxing and contracting effects of theophylline's metabolites on the rabbit upper gastrointestinal tract.	2008-10	18844725
Anti-inflammatory effect of theophylline in rats and its involvement of the glucocorticoid-glucocorticoid receptor system.	2008-04	18391482
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.	2007-12	17991222
Possible involvement of organic anion and cation transporters in renal excretion of xanthine derivatives, 3-methylxanthine and enprofylline.	2007-09-22	17897683
Associations between CYP2E1 promoter polymorphisms and plasma 1,3-dimethyluric acid/theophylline ratios.	2006-08	16841220
Towards the design of highly selective recognition sites into molecular imprinting polymers: a computational approach.	2006-07-15	16806890
Liver dysfunction markedly decreases the inhibition of cytochrome P450 1A2-mediated theophylline metabolism by fluvoxamine.	2006-05	16678550
Theophylline pharmacokinetics: comparison of Cyp1a1(-/-) and Cyp1a2(-/-) knockout mice, humanized hCYP1A1_1A2 knock-in mice lacking either the mouse Cyp1a1 or Cyp1a2 gene, and Cyp1(+/+) wild-type mice.	2005-07	15970798
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
High-throughput liquid chromatography-tandem mass spectrometry assay for plasma theophylline and its metabolites.	2004-11	15502093
Genetic screens and selections for small molecules based on a synthetic riboswitch that activates protein translation.	2004-10-20	15479078
Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples.	2004-10	15537072
Catabolism of caffeine in plants and microorganisms.	2004-05-01	14977550
Biosynthesis, accumulation and degradation of theobromine in developing Theobroma cacao fruits.	2004-04	15128023
Group I aptazymes as genetic regulatory switches.	2002-12-04	12466025
Structural basis for the binding affinity of xanthines with the DNA intercalator acridine orange.	2001-12-20	11741482
Dose dependent pharmacokinetics of theophylline: Michaelis-Menten parameters for its major metabolic pathways.	2001-09-14	11554438
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.	2001-08-15	11499474
Determination of urinary methylated purine pattern by high-performance liquid chromatography.	2001-02-10	11232859
Caffeine metabolism before and after liver transplantation.	2001-02	11270802
Theophylline metabolism after cardiac surgery.	2001-02	11210395
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.	2001-01	11204934
Neurotoxic convulsions induced by theophylline and its metabolites in mice.	1996-06	8799489
Structure-activity relationships for the binding of ligands to xanthine or guanine phosphoribosyl-transferase from Toxoplasma gondii.	1995-11-09	7503772
Cystic fibrosis: enhanced theophylline metabolism may be linked to the disease.	1988-09	3046811
Theophylline metabolism: variation and genetics.	1984-02	6362955
Theobromine kinetics and metabolic disposition.	1983-10	6617078
Determination of theophylline and its metabolites by liquid chromatography.	1977-12	591601

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:31:22 GMT 2025` Edited by `admin` on `Mon Mar 31 19:31:22 GMT 2025`
Record UNII	WS6X982OEC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THEOPHYLLINE IMPURITY B [EP IMPURITY]

Preferred Name

English

3-METHYLXANTHINE

Systematic Name

English

THEOPHYLLINE RELATED COMPOUND B

Common Name

English

PENTOXIFYLLINE IMPURITY B [EP IMPURITY]

Common Name

English

THEOPHYLLINE MONOHYDRATE IMPURITY B [EP IMPURITY]

Common Name

English

3 MX

Common Name

English

THEOPHYLLINE RELATED COMPOUND B [USP IMPURITY]

Common Name

English

3-METHYL-3,7-DIHYDRO-1H-PURINE-2,6-DIONE

Systematic Name

English

NSC-515466

Code

English

THEOPHYLLINE RELATED COMPOUND B [USP-RS]

Common Name

English

Code System Code Type Description

PUBCHEM

70639