Basic information
- CAS
1076-22-8- Standard SMILES
Cn1c(=O)[nH]c(=O)c2[nH]cnc21- InChIKey
GMSNIKWWOQHZGF-UHFFFAOYSA-N- Molecular formula
- C6H6N4O2
- Average molar mass
- 166.14 g/mol
- Monoisotopic mass
- 166.04907543
Overview
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.
Names & identifiers
- Preferred name
- 3-Methylxanthine
- IUPAC
- 3-methyl-7H-purine-2,6-dione
- English name
- 3-Methylxanthine
- Molecular formula
- C6H6N4O2
- Molecular weight
- 166.14
Names & synonyms
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
Show more names
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
Database identifiers
- 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
Properties
Computed structural properties
- XLogP
- -0.7
- Topological polar surface area
- 78.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 242
Experimental & physicochemical properties
DrugsPharmaceuticals -> Metabolite of Caffeine, Theophylline
LogP
-0.50
-0.72
Melting Point> 300 °C
Physical DescriptionSolid
Collision Cross Section
127.59 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
124.48 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
127.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 300 °C · >300 °C (lit.)
- Boiling point
- 294.33 °C · 294.33°C (rough estimate)
- Density
- 1.4434 · 1.4434 (rough estimate)
- refractive index
- 1.67 · 1.6700 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly, Heated), Methanol (Slightly)
- form
- Solid
- pka
- 1 · pK1:8.10;pK2:11.3 (25°C)
- color
- White to Pale Beige
- Water Solubility
- 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 DataBase Reference
- 1076 · 1076-22-8(CAS DataBase Reference)
- FDA UNII
- 6 X982OEC · WS6X982OEC
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,T+
- Risk Statements
- 22 · 22-26/27/28
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 1 · 1
- RTECS
- 8750000 · ZD8750000
- HS Code
- 29335990 · 29335990
- Storage Class
- 11 · 11 - Combustible Solids
- Toxicity
- 50 intraperitoneal · LD50 intraperitoneal in mouse: 894mg/kg
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
Regulatory InformationStatus: Active Update: 20-05-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17492
Hazard Classes and CategoriesAcute Tox. 4 (98.1%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 1
- rtecs
- ZD8750000
- hs_code
- 29335990
- Toxicity
- LD50 intraperitoneal in mouse: 894mg/kg
- risk_code
- 22-26/27/28
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T+
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- REACH Registrations
- Active
- Precautionary statements
- P301+P312+P330
Chemistry & industry
Pharmacology
Metabolism/Metabolites3-Methylxanthine is a known human metabolite of theobromine and theophylline.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Applications
Description3-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].
Uses3-Methylxanthine is a Xanthine derivative with diuretic, cardiac stimulant and smooth muscle relaxant activities; isomeric with theobromine.They can also act as Bronchodilator.
General Description3-Methylxanthine, a metabolite of theophylline, was quantitated in rat plasma by a sensitive LC-MS/MS method.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
宁波君龙新材料有限公司0574 88552216 19032109277 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎（中国）化学有限公司400-6106006 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
安庆奇创药业有限公司18061456370
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海相辉医药科技有限公司13761987713 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
上海升华医药科技有限公司021-50793966 18917198199
Beckmann-Kenko GmbH+49 4241 9308 88 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
大赛璐药物手性技术（上海）有限公司021-50460086-9 15921403865 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
南京维奥化工有限公司Please Send Email 18652950785 · [email protected]
上海珂华生物科技有限公司021-60455363 18019463053 · [email protected]
济南邦德化工技术有限公司86-531-88280989 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
山东铭枫医药科技有限公司053155551677 15315114555 · [email protected]
赛默飞世尔科技（中国）有限公司800-810-5118 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
广州安信医药有限公司00000
上海贤鼎生物科技有限公司4009209199 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
Shanghai Witofly Chemical Co.,Ltd[email protected]
越林试剂021-62960152 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
沧州那瑞化学科技有限公司+86-317-3563899 · [email protected]
上海昶衍化工科技有限公司021-20242659 18930833303 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
上海鑫圭生物科技有限公司15121041756 · [email protected]
天津安浩生物科技有限公司[email protected]
武汉励合化学新材料有限公司027-88395709
上海嵩爰化工科技有限公司010-1234567 18521000990 · [email protected]
南京恰风和医药科技有限公司025-57018978 18251899859 · [email protected]
上海有朋化工有限公司021-69005955 13701776567 · [email protected]
北京海力扬化学科技有限公司13718199399 · [email protected]
四川海诺威科技有限公司13708085536 13708085536 · [email protected]
江苏艾康生物医药研发有限公司025-66028182 17714375163 · [email protected]
上海凯赛化工有限公司021-33516722 13701817765 · [email protected]
Additional notes
DefinitionChEBI: 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.
Related reactions
55 records
Compound notes
Loading…