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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 of 7-METHYLXANTHINE

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

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

PubMed

PubMed

TitleDatePubMed
Caffeine metabolism before and after liver transplantation.
2001 Feb
7-Methylxanthine methyltransferase of coffee plants. Gene isolation and enzymatic properties.
2001 Mar 16
Group I aptazymes as genetic regulatory switches.
2002 Dec 4
[Research on the separation of caffeine and its nine analogues by micellar electrokinetic capillary chromatography].
2002 May
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 Oct 15
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 Jan 16
Catabolism of caffeine in plants and microorganisms.
2004 May 1
Methylated purines in urinary stones.
2005 Aug
Altered expression of the caffeine synthase gene in a naturally caffeine-free mutant of Coffea arabica.
2009 Oct
Carotenoids in clams, Ruditapes philippinarum and Meretrix petechialis.
2010 May 12

Sample Use Guides

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
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 Fri Dec 15 17:48:39 GMT 2023
Edited
by admin
on Fri Dec 15 17:48:39 GMT 2023
Record UNII
E9M81NJM6G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
METHYL XANTHINE
INCI  
INCI  
Official Name English
HETEROXANTHINE
Common Name English
7-METHYLXANTHIN
Systematic Name English
METHYL XANTHINE [INCI]
Common Name English
Code System Code Type Description
PUBCHEM
68374
Created by admin on Fri Dec 15 17:48:39 GMT 2023 , Edited by admin on Fri Dec 15 17:48:39 GMT 2023
PRIMARY
FDA UNII
E9M81NJM6G
Created by admin on Fri Dec 15 17:48:39 GMT 2023 , Edited by admin on Fri Dec 15 17:48:39 GMT 2023
PRIMARY
CAS
552-62-5
Created by admin on Fri Dec 15 17:48:39 GMT 2023 , Edited by admin on Fri Dec 15 17:48:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID60203696
Created by admin on Fri Dec 15 17:48:39 GMT 2023 , Edited by admin on Fri Dec 15 17:48:39 GMT 2023
PRIMARY
CHEBI
48991
Created by admin on Fri Dec 15 17:48:39 GMT 2023 , Edited by admin on Fri Dec 15 17:48:39 GMT 2023
PRIMARY
NSC
7861
Created by admin on Fri Dec 15 17:48:39 GMT 2023 , Edited by admin on Fri Dec 15 17:48:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
209-019-0
Created by admin on Fri Dec 15 17:48:39 GMT 2023 , Edited by admin on Fri Dec 15 17:48:39 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
PERCENT OF AMOUNT EXCRETED
MAJOR
PLASMA; URINE