3-Methylxanthine

Names

[ Name ]:
3-Methylxanthine

[Synonym ]:
6-Hydroxy-3-methyl-3,9-dihydro-2H-purin-2-one
3-METHYL XANTHINE
3-METHYL-2,3,6,9-TETRAHYDRO-1H-PURINE-2,6-DIONE
3,7-dihydro-3-methyl-1h-purine-6-dione
1H-PURINE-2,6-DIONE,3,9-DIHYDRO-3-METHYL-
3-methyl-7H-purine-2,6-dione
2,6-Dihydroxy-3-methylpurine
3-Methyl-3,7-dihydro-1H-purine-2,6-dione
3,7-DIHYDRO-3-METHYL-1H-PURINE-2,6-DIONE
3-Methyl-1H-purine-2,6(3H,7H)-dione
EINECS 214-058-1
MFCD00005580
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]:

3-Methylxanthine, a xanthine derivative, is a cyclic guanosine monophosphate (GMP) inhibitor, with an IC50 of 920 μM on guinea-pig isolated trachealis muscle.

[Related Catalog]:

Research Areas >> Others

Natural Products >> Saccharides and Glycosides

[Target]

GMP:920 μM (IC50)

Human Endogenous Metabolite

[References]

[1]. Tanaka H, et al. Inhibition of cyclic GMP phosphodiesterase by xanthine derivatives relaxes guinea-pig trachealis smooth muscle. Clin Exp Pharmacol Physiol. 1991 Mar;18(3):163-8.

[2]. Yamamoto K, et al. Neurotoxic convulsions induced by theophylline and its metabolites in mice. Biol Pharm Bull. 1996 Jun;19(6):869-72.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
322.4ºC at 760 mmHg

[ Melting Point ]:
>300 °C(lit.)

[ Molecular Formula ]:
C₆H₆N₄O₂

[ Molecular Weight ]:
166.137

[ Flash Point ]:
148.8ºC

[ Exact Mass ]:
166.049072

[ PSA ]:
83.54000

[ LogP ]:
-0.79

[ Vapour Pressure ]:
2.23E-05mmHg at 25°C

[ Index of Refraction ]:
1.627

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: ZD8750000

CHEMICAL NAME :: Xanthine, 3-methyl-

CAS REGISTRY NUMBER :: 1076-22-8

LAST UPDATED :: 199706

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C6-H6-N4-O2

MOLECULAR WEIGHT :: 166.16

WISWESSER LINE NOTATION :: T56 BM DN FNVMVJ F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >500 mg/kg

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

REFERENCE :: NCNSA6 National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. (Washington, DC) Volume(issue)/page/year: 5,23,1953

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 894 mg/kg

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

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 25,653,1990

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 300 mg/kg

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

REFERENCE :: AEXPBL Archiv fuer Experimentelle Pathologie und Pharmakologie. (Leipzig, Ger. Dem. Rep.) V.1-109, 1873-1925. For publisher information, see NSAPCC. Volume(issue)/page/year: 43,305,1900

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 500 mg/kg

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

REFERENCE :: AEXPBL Archiv fuer Experimentelle Pathologie und Pharmakologie. (Leipzig, Ger. Dem. Rep.) V.1-109, 1873-1925. For publisher information, see NSAPCC. Volume(issue)/page/year: 43,305,1900

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Amphibian - frog

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - other changes

REFERENCE :: AEXPBL Archiv fuer Experimentelle Pathologie und Pharmakologie. (Leipzig, Ger. Dem. Rep.) V.1-109, 1873-1925. For publisher information, see NSAPCC. Volume(issue)/page/year: 43,305,1900 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1600 mg/kg/16D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - hematuria Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

REFERENCE :: JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 4,304,1984

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Precautionary Statements ]:
P301 + P312 + P330

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
1

[ RTECS ]:
ZD8750000

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Customs

[ HS Code ]: 2942000000