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 2565

PubMed

Title	Date	PubMed
Determination of theophylline and its metabolites by liquid chromatography.	1977 Dec	591601
Theobromine kinetics and metabolic disposition.	1983 Oct	6617078
Theophylline metabolism: variation and genetics.	1984 Feb	6362955
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
Structural basis for the binding affinity of xanthines with the DNA intercalator acridine orange.	2001 Dec 20	11741482
Caffeine metabolism before and after liver transplantation.	2001 Feb	11270802
Theophylline metabolism after cardiac surgery.	2001 Feb	11210395
Determination of urinary methylated purine pattern by high-performance liquid chromatography.	2001 Feb 10	11232859
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
Genetic screens and selections for small molecules based on a synthetic riboswitch that activates protein translation.	2004 Oct 20	15479078
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 Jul	15970798
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Associations between CYP2E1 promoter polymorphisms and plasma 1,3-dimethyluric acid/theophylline ratios.	2006 Aug	16841220
Towards the design of highly selective recognition sites into molecular imprinting polymers: a computational approach.	2006 Jul 15	16806890
Liver dysfunction markedly decreases the inhibition of cytochrome P450 1A2-mediated theophylline metabolism by fluvoxamine.	2006 May	16678550
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
Possible involvement of organic anion and cation transporters in renal excretion of xanthine derivatives, 3-methylxanthine and enprofylline.	2007 Sep 22	17897683
Anti-inflammatory effect of theophylline in rats and its involvement of the glucocorticoid-glucocorticoid receptor system.	2008 Apr	18391482
A simple HPLC method for the quantification of mizoribine in human serum: pharmacokinetic applications.	2008 Nov	18661478
Relaxing and contracting effects of theophylline's metabolites on the rabbit upper gastrointestinal tract.	2008 Oct	18844725
Demethylation of theophylline (1,3-dimethylxanthine) to 1-methylxanthine: the first step of an antioxidising cascade.	2010	20594417
Ultrafast dynamics show that the theophylline and 3-methylxanthine aptamers employ a conformational capture mechanism for binding their ligands.	2010 Apr 6	20214401

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 `Thu Jul 06 02:11:50 UTC 2023` Edited by `admin` on `Thu Jul 06 02:11:50 UTC 2023`
Record UNII	WS6X982OEC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

THEOPHYLLINE 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