1-Methylxanthine

Names

[ Name ]:
1-Methylxanthine

[Synonym ]:
methyl xanthine
6-Hydroxy-3-methyl-3,9-dihydro-2H-purin-2-one
1-Methyl-3,7-dihydro-1H-purine-2,6-dione
methylxanthine
1H-Purine-2,6-dione, 3,7-dihydromethyl-
3-Methyl-3,7-dihydro-1H-purine-2,6-dione
1H-Purine-2,6-dione, 3,7-dihydro-1-methyl-
1-Methylxanthine
1-methyl-7H-xanthine
MFCD00005561
1-Methyl Xanthine
1-methyl-3,7-dihydropurine-2,6-dione
EINECS 228-108-5
3-Methylxanthine
1H-Purine-2,6-dione, 3,7-dihydro-3-methyl-
2H-Purin-2-one, 3,9-dihydro-6-hydroxy-3-methyl-
oxoguanine

Biological Activity

[Description]:

1-Methylxanthine, a caffeine derivative, is an essential human urinary metabolite of caffeine and theophylline (1,3-dimethylxanthine, TP)[1]. 1-Methylxanthine enhances the radiosensitivity of tumor cells[2].

[Related Catalog]:

Research Areas >> Cancer

[Target]

Human Endogenous Metabolite

[In Vitro]

1-Methylxanthine (1-MTX; 3 mM; for 30 min) increases the radiation-induced clonogenic and apoptotic cell (RKO human colorectal cancer cells carrying wild type protein 53 kDa (p53)) death[2]. 1-Methylxanthine (1MX) exhibits similar activities to other naturally occurring methylxanthines. Unlike caffeine, TP, and theobromine, 3-Methylxanthine (3MX) and 1-methylxanthine do not occur naturally at high levels in plants[1].

[References]

[1]. Algharrawi KH, et al. Direct conversion of theophylline to 3-methylxanthine by metabolically engineered E. coli. Microb Cell Fact. 2015 Dec 21;14:203.

[2]. Youn H, et al. 1-Methylxanthine enhances the radiosensitivity of tumor cells. Int J Radiat Biol. 2009 Feb;85(2):167-74.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Melting Point ]:
≥300 °C

[ Molecular Formula ]:
C₆H₆N₄O₂

[ Molecular Weight ]:
166.137

[ Exact Mass ]:
166.049072

[ PSA ]:
83.54000

[ LogP ]:
-1.52

[ Index of Refraction ]:
1.627

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: ZD8575000

CHEMICAL NAME :: Xanthine, 1-methyl-

CAS REGISTRY NUMBER :: 6136-37-4

LAST UPDATED :: 199706

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C6-H6-N4-O2

MOLECULAR WEIGHT :: 166.16

WISWESSER LINE NOTATION :: T56 BM DN FMVNVJ H1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 510 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 24,393,1973 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5255 No. of Facilities: 25 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 2440 (estimated) No. of Female Employees: 1459 (estimated)

Safety Information

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
R26/27/28

[ Safety Phrases ]:
S22-S24/25

[ WGK Germany ]:
3

[ RTECS ]:
ZD8575000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%