3,7-Dihydro-3-methyl-1H-purin-2,6-dion

3-Methylxanthine

HCID 70639CAS 1076-22-8

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Grundinformationen

Standard-SMILES: Cn1c(=O)[nH]c(=O)c2[nH]cnc21
InChIKey: GMSNIKWWOQHZGF-UHFFFAOYSA-N
Summenformel: C6H6N4O2
Durchschnittliche Molmasse: 166,14 g/mol
Monoisotopische Masse: 166,04907543

Überblick

3-methyl-9H-xanthine is a 3-methylxanthine tautomer where the imidazole proton is located at the 9-position. It has a role as a metabolite. It is a tautomer of a 3-methyl-7H-xanthine.

Namen und Bezeichner

Bevorzugter Name: 3-Methylxanthine
IUPAC: 3-methyl-7H-purine-2,6-dione
Lokaler Name: 3,7-Dihydro-3-methyl-1H-purin-2,6-dion
Englischer Name: 3-Methylxanthine
Summenformel: C6H6N4O2
Molmasse: 166.14

Namen und Synonyme

3-Methylxanthine1076-22-83-methyl-7H-purine-2,6-dione3-methyl-3,7-dihydro-1H-purine-2,6-dione3-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dioneWS6X982OECDTXSID90148107NSC-515466RefChem:94981DTXCID8070598CHEBI:62205214-058-1

Weitere Namen anzeigen

3-MethylxantineLinaint-EAKOS NCG-00583-Methy-xanthine3-methyl-xanthinZotepine Impurity63-Methylxanthine>3-methyl-7H-xanthine

2,6-Dihydroxy-3-methylpurine3-Methyl-1H-purine-2,6(3H,7H)-dione3 MXXanthine, 3-methyl-3-METHYL XANTHINE1H-Purine-2,6-dione, 3,7-dihydro-3-methyl-MFCD000055803,7-Dihydro-3-methyl-1H-purine-2,6-dione

Datenbank-Bezeichner

CAS: 1076-22-8
PubChem CID: 70639
DTXSID: DTXSID90148107
ChEMBL: CHEMBL619
ChEBI: CHEBI:62207
UNII: WS6X982OEC
EC Number: 214-058-1
Nikkaji: J3.360J、J492.513K

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -0,7
Polarare Oberfläche (TPSA): 78,1 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 0
Schwere Atome: 12
Formalladung: 0
Komplexität: 242

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Metabolite of Caffeine, Theophylline

LogP · 2 Einträge

-0.50

-0.72

Melting Point> 300 °C

Physical DescriptionSolid

Collision Cross Section · 3 Einträge

127.59 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

124.48 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

127.9 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt: 300 °C · >300 °C (lit.)
Siedepunkt: 294.33 °C · 294.33°C (rough estimate)
Dichte: 1.4434 · 1.4434 (rough estimate)
Brechungsindex: 1.67 · 1.6700 (estimate)
storage temp.: 2 · 2-8°C
Löslichkeit: DMSO (Slightly, Heated), Methanol (Slightly)
Aggregatzustand: Solid
pka: 1 · pK1:8.10;pK2:11.3 (25°C)
Farbe: White to Pale Beige
Wasserlöslichkeit: Insoluble in water.
BRN: 180944 · 180944
InChI: InChI=1S/C6H6N4O2/c1-10-4-3(7-2-8-4)5(11)9-6(10)12/h2H,1H3,(H,7,8)(H,9,11,12)
InChIKey: GMSNIKWWOQHZGF-UHFFFAOYSA-N
SMILES: N1C2=C(N(C)C(=O)NC2=O)NC=1
CAS Datenbank: 1076 · 1076-22-8(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (98.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 53 reports by companies from 4 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 20-05-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17492

Hazard Classes and CategoriesAcute Tox. 4 (98.1%)

Sicherheitsdaten

wgk: 1
hs_code: 29335990
RTECS-Nr.: ZD8750000
risk_code: 22-26/27/28
Toxizität: LD50 intraperitoneal in mouse: 894mg/kg
hazard_code: Xn,T+
safety_code: 22-24/25
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites3-Methylxanthine is a known human metabolite of theobromine and theophylline.

Tissue LocationsKidney

Cellular LocationsCytoplasm

Anwendungen · 2 Einträge

Beschreibung3-Methylxanthine is one of the metabolites of theophylline. After oral intake, approximately 36% is excreted in the urine as 3-methylxanthine, 40% as 1,3-dimethyluric acid and 17% as 1-methyluric acid. 3-methylxanthine (3MX) has been assessed as an adenosine antagonist and produces the same maximal relaxation of guinea pig tracheal muscle as does. 3MX is also used to examine conformational heterogeneity in RNA aptamers and riboswitches[1-2].

Verwenden3-Methylxanthine is a Xanthine derivative with diuretic, cardiac stimulant and smooth muscle relaxant activities; isomeric with theobromine.They can also act as Bronchodilator.