7-METHYLXANTHINE

Investigational

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

CN1C=NC2=C1C(=O)NC(=O)N2

InChI

InChIKey=PFWLFWPASULGAN-UHFFFAOYSA-N

InChI=1S/C6H6N4O2/c1-10-2-7-4-3(10)5(11)9-6(12)8-4/h2H,1H3,(H2,8,9,11,12)

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: http://www.hmdb.ca/metabolites/HMDB0001991 | https://www.ncbi.nlm.nih.gov/pubmed/29386874 | https://www.ncbi.nlm.nih.gov/pubmed/20072638

7-Methylxanthine is a methyl derivative of xanthine, found occasionally in human urine. 7-Methylxanthine is one of the purine components in urinary calculi. 7-methylxanthine (7-MX) is a metabolite of caffeine and theobromine, and has been shown to have low toxicity and no carcinogenic effects. 7-MX is known as a non-selective adenosine antagonist and has been shown to work against myopia. 7-MX has little effect on the proliferation or apoptosis of human RPE cells; however, 7-MX disturbs the proportion of cells in the G1 stage and inhibits the expression of ADORA1, ADORA2A, and ADORA2B in short-term treatment. 7-MX has been confirmed to reduce the severity of myopia and eye elongation induced by forming deprivation in guinea pigs and to counteract the thinning of the posterior sclera and of collagen fibrils induced by form deprivation. A clinical trial showed that 7-MX reduced eye elongation and myopia progression in childhood myopia.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A1 receptor 54 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8230124/ \| https://www.ncbi.nlm.nih.gov/pubmed/20072638	Blocker 555
Adenosine A2 receptor 9 Target ID: CHEMBL2094257 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8230124/ \| https://www.ncbi.nlm.nih.gov/pubmed/20072638	Blocker 555

PubMed

Title	Date	PubMed
Adenosine receptor protein changes in guinea pigs with form deprivation myopia.	2010-11	19604158
Carotenoids in clams, Ruditapes philippinarum and Meretrix petechialis.	2010-05-12	20397729
Altered expression of the caffeine synthase gene in a naturally caffeine-free mutant of Coffea arabica.	2009-10	21637458
Systemic 7-methylxanthine in retarding axial eye growth and myopia progression: a 36-month pilot study.	2008-12	20072638
Non-standard base pairing and stacked structures in methyl xanthine clusters.	2008-05-21	18464999
Distribution of adenosine receptors in human sclera fibroblasts.	2008-03-14	18385786
Degradation kinetics of caffeine and related methylxanthines by induced cells of Pseudomonas sp.	2007-07	17554468
Coffee and tomato share common gene repertoires as revealed by deep sequencing of seed and cherry transcripts.	2005-12	16273343
Methylated purines in urinary stones.	2005-08	15919878
Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection.	2005-05-25	15833286
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.	2004-10-11	15372679
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
Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants.	2003-05	12746542
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.).	2003-01-16	12527364
Group I aptazymes as genetic regulatory switches.	2002-12-04	12466025
Identification of N1-methyl-2-pyridone-5-carboxamide and N1-methyl-4-pyridone-5-carboxamide as components in urine extracts of individuals consuming coffee.	2002-10-15	12367703
Differences in caffeine and paraxanthine metabolism between human and murine CYP1A2.	2002-06-15	12110375
[Research on the separation of caffeine and its nine analogues by micellar electrokinetic capillary chromatography].	2002-05	12541944
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
Oral pentoxifylline inhibits release of tumor necrosis factor-alpha from human peripheral blood monocytes : a potential treatment for aseptic loosening of total joint components.	2001-07	11451976
7-Methylxanthine methyltransferase of coffee plants. Gene isolation and enzymatic properties.	2001-03-16	11108716
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
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis.	2001-01	11204934

Sample Use Guides

In Vivo Use Guide

During a 12-months placebo-controlled trial, participants received one tablet every morning. The tablets had a diameter of 12 mm and a thickness of 3 mm. Active tablets contained 400 mg 7-MX. The peak serum concentration after an oral dose of 400 mg 7-MX in adults is around 20 umol/l with a half-life of 200 min.

Route of Administration: Oral

In Vitro Use Guide

To observe the growth of cells treated with 7-MX, primary human RPE cells were incubated with different concentrations (from 1 nmol/l to 1 mmol/l) of 7-MX. No statistically significantly growth alteration was noted at 24, 72, and 96 h. A slightly decreased cell proliferation rate was seen with 100 umol/l 7-MX at 48 h, but without statistically significant differences compared to the other concentrations. To observe the effects of 7-MX on the mRNA levels of ADORs, RPE cells were cultured with 10 umol/l 7-MX for 24, 48, and 72 h.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:53:23 GMT 2025` Edited by `admin` on `Mon Mar 31 18:53:23 GMT 2025`
Record UNII	E9M81NJM6G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHYL XANTHINE

Preferred Name

English

7-METHYLXANTHINE

Systematic Name

English

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

Systematic Name

English

NSC-7861

Code

English

METHYLXANTHINE, 7-

Systematic Name

English

HETEROXANTHINE

Common Name

English

7-METHYLXANTHIN

Systematic Name

English

Code System Code Type Description

PUBCHEM

68374