3-Methylxanthine

3-METHYLXANTHINE · 3-Methyl-3,7-dihydro-1H-purine-2,6-dione · 3-Methylxantine · Linaint-E · AKOS NCG-0058 · 3-Methy-xanthine · 3-methyl-xanthin · Zotepine Impurity6

https://huagongshe.com/en/chemical/70639

Identifiers & Physical Properties

CAS No.	1076-22-8
Molecular formula	C6H6N4O2
Average molar mass	166.14 g/mol
Monoisotopic mass	166.04907543 g/mol
SMILES	Cn1c(=O)[nH]c(=O)c2[nH]cnc21
InChIKey	GMSNIKWWOQHZGF-UHFFFAOYSA-N
PubChem CID	70639
ChEMBL	CHEMBL619
ChEBI	CHEBI:62207
EC No.	214-058-1
DTXSID	DTXSID90148107

Chemical & Physical Properties

XLogP	-0.7
Topological polar surface area	78.1
Hydrogen bond donors	2
Hydrogen bond acceptors	3
Rotatable bonds	0
Heavy atoms	12
Formal charge	0
Complexity	242
Drugs	Pharmaceuticals -> Metabolite of Caffeine, Theophylline
LogP (partition coefficient)	-0.50-0.72
Melting point	> 300 °C>300 °C (lit.)
Physical Description	Solid
Collision Cross Section	127.59 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]124.48 Å² [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]127.9 Å² [M+H]+ [CCS Type: TW
Boiling point	294.33°C (rough estimate)
Density	1.4434 (rough estimate)
Refractive index	1.6700 (estimate)
Storage conditions	2-8°C
Solubility	DMSO (Slightly, Heated), Methanol (Slightly)Insoluble in water.
Physical state	Solid
pKa (acidity coefficient)	pK1:8.10pK2:11.3 (25°C)
Color	White to Pale Beige
BRN	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	1076-22-8(CAS DataBase Reference)
FDA UNII	WS6X982OEC
UNSPSC Code	41116107
NACRES	NA.24
GHS pictogram	GHS07
Signal word	Warning
GHS hazard statements	H302
GHS precautionary statements	P301+P312+P330
Personal protective equipment (PPE)	dust mask type N95 (US), Eyeshields, Gloves
Hazard symbols	Xn,T+
Risk statements (R)	22-26/27/28
Safety statements (S)	22-24/25
Water hazard class (WGK)	1
RTECS number	ZD8750000
Customs code	29335990
Storage class	11 - Combustible Solids
Toxicity	LD50 intraperitoneal in mouse: 894mg/kg
REACH registrations	Active

Safety & Regulations

GHS classification	WarningH302 (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.
Regulatory information	Status: Active Update: 20-05-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17492
Hazard Classes and Categories	Acute Tox. 4 (98.1%)
Personal protective equipment (PPE)	dust mask type N95 (US), Eyeshields, Gloves
Water hazard class (WGK)	1
RTECS number	ZD8750000
Customs code	29335990
Toxicity	LD50 intraperitoneal in mouse: 894mg/kg
Risk statements (R)	22-26/27/28
Signal word	Warning
GHS pictogram	GHS07
Hazard symbols	Xn,T+
Safety statements (S)	22-24/25
Storage class	11 - Combustible Solids
GHS hazard statements	H302
REACH registrations	Active
GHS precautionary statements	P301+P312+P330

Applications & Uses

Description

3-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].

Uses

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

General Description

3-Methylxanthine, a metabolite of theophylline, was quantitated in rat plasma by a sensitive LC-MS/MS method.