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
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)
| 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
| Title | Date | PubMed |
|---|---|---|
| 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 Aug 15 |
|
| Caffeine metabolism before and after liver transplantation. | 2001 Feb |
|
| Determination of urinary methylated purine pattern by high-performance liquid chromatography. | 2001 Feb 10 |
|
| Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis. | 2001 Jan |
|
| 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 Jul |
|
| 7-Methylxanthine methyltransferase of coffee plants. Gene isolation and enzymatic properties. | 2001 Mar 16 |
|
| Group I aptazymes as genetic regulatory switches. | 2002 Dec 4 |
|
| Differences in caffeine and paraxanthine metabolism between human and murine CYP1A2. | 2002 Jun 15 |
|
| [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 |
|
| Molecular cloning and functional characterization of three distinct N-methyltransferases involved in the caffeine biosynthetic pathway in coffee plants. | 2003 May |
|
| Catabolism of caffeine in plants and microorganisms. | 2004 May 1 |
|
| Separation, pre-concentration, and HPLC analysis of methylxanthines in urine samples. | 2004 Oct |
|
| 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 Oct 11 |
|
| Methylated purines in urinary stones. | 2005 Aug |
|
| Coffee and tomato share common gene repertoires as revealed by deep sequencing of seed and cherry transcripts. | 2005 Dec |
|
| Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection. | 2005 May 25 |
|
| Degradation kinetics of caffeine and related methylxanthines by induced cells of Pseudomonas sp. | 2007 Jul |
|
| Systemic 7-methylxanthine in retarding axial eye growth and myopia progression: a 36-month pilot study. | 2008 Dec |
|
| Distribution of adenosine receptors in human sclera fibroblasts. | 2008 Mar 14 |
|
| Non-standard base pairing and stacked structures in methyl xanthine clusters. | 2008 May 21 |
|
| 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 |
|
| Adenosine receptor protein changes in guinea pigs with form deprivation myopia. | 2010 Nov |
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
Edited
Thu Jul 06 01:06:01 UTC 2023
by
admin
on
Thu Jul 06 01:06:01 UTC 2023
|
| Record UNII |
E9M81NJM6G
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
68374
Created by
admin on Thu Jul 06 01:06:01 UTC 2023 , Edited by admin on Thu Jul 06 01:06:01 UTC 2023
|
PRIMARY | |||
|
E9M81NJM6G
Created by
admin on Thu Jul 06 01:06:01 UTC 2023 , Edited by admin on Thu Jul 06 01:06:01 UTC 2023
|
PRIMARY | |||
|
552-62-5
Created by
admin on Thu Jul 06 01:06:01 UTC 2023 , Edited by admin on Thu Jul 06 01:06:01 UTC 2023
|
PRIMARY | |||
|
DTXSID60203696
Created by
admin on Thu Jul 06 01:06:01 UTC 2023 , Edited by admin on Thu Jul 06 01:06:01 UTC 2023
|
PRIMARY | |||
|
48991
Created by
admin on Thu Jul 06 01:06:01 UTC 2023 , Edited by admin on Thu Jul 06 01:06:01 UTC 2023
|
PRIMARY | |||
|
7861
Created by
admin on Thu Jul 06 01:06:01 UTC 2023 , Edited by admin on Thu Jul 06 01:06:01 UTC 2023
|
PRIMARY | |||
|
209-019-0
Created by
admin on Thu Jul 06 01:06:01 UTC 2023 , Edited by admin on Thu Jul 06 01:06:01 UTC 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> METABOLITE |
PERCENT OF AMOUNT EXCRETED
MAJOR
PLASMA; URINE
|
