Paraxanthine

HCID 4687CAS 611-59-6
Substructure searchFind similar structures

Basic information

Standard SMILES
Cn1c(=O)[nH]c2ncn(C)c2c1=O
InChIKey
QUNWUDVFRNGTCO-UHFFFAOYSA-N
Molecular formula
C7H8N4O2
Average molar mass
180.16 g/mol
Monoisotopic mass
180.06472551

Names & identifiers

Preferred name
Paraxanthine
IUPAC
1,7-dimethyl-3H-purine-2,6-dione
English name
1,7-Dimethylxanthine
Molecular formula
C7H8N4O2
Molecular weight
180.16

Names & synonyms

paraxanthine1,7-Dimethylxanthine611-59-6p-Xanthine1,7-dimethyl-3H-purine-2,6-dione1H-Purine-2,6-dione, 3,7-dihydro-1,7-dimethyl-DTXSID20522811,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione1,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dioneNSC-400018Q3565Y41V7DTXCID2030853
Show more names
Paraxanthin1,7-Dimethyl-1H-purine-2,6-dione, 1,7-Dimethylxanthine, 2,6-Dihydroxy-1,7-dimethylpurine, ParaxanthineParaxanthine-d3Paraxanthine solution
CHEBI:25858RefChem:417792210-271-91,7-Dimethyl-1H-purine-2,6(3H,7H)-dione3,7-Dihydro-1,7-dimethyl-1H-purine-2,6-dioneXanthine, 1,7-dimethyl-Caffeine Impurity FCaffeine EP Impurity F

Database identifiers

CAS
611-59-6
PubChem CID
4687
DTXSID
DTXSID2052281
ChEMBL
CHEMBL1158
ChEBI
CHEBI:25858
UNII
Q3565Y41V7
EC Number
210-271-9
Nikkaji
J2.991B

Properties

Computed structural properties

XLogP
-0.2
Topological polar surface area
67.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
13

Experimental & physicochemical properties

Solubility>27 [ug/mL] (The mean of the results at pH 7.4)
Melting Point351 - 352 °C
Physical Description · 2 items

Faint yellow fine crystals; [MSDSonline]

Solid

Collision Cross Section · 6 items

134.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID2052281]；136.8 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID2052281]

149.5 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；134 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]；138.7 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

130.85 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；137.69 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；125.98 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]；138.86 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

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

135.63 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

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

Physicochemical properties

Melting point
294 · 294-296 °C (lit.)
Boiling point
312.97 °C · 312.97°C (rough estimate)
Density
1.364 · 1.3640 (rough estimate)
refractive index
1.67 · 1.6700 (estimate)
Flash point
9 ℃ · 9℃
storage temp.
room temp

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 6.7% (3 of 45) of reports.

Warning

H302 (93.3%): 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 45 reports by companies from 3 notifications to the ECHA C&L Inventory.；Reported as not meeting GHS hazard criteria per 3 of 45 reports by companies.；There are 2 notifications provided by 42 of 45 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazards SummaryA skin, eye, and respiratory tract irritant; [MSDSonline]
Hazard Classes and CategoriesAcute Tox. 4 (93.3%)

Toxicology

USGS Health-Based Screening Levels for Evaluating Water-Quality · 3 items

1,7-Dimethylxanthine

Pharmaceutical

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
rtecs
RV9380000
ridadr
UN1230 - class 3 - PG 2 - Methanol, solution
hs_code
2933.59.9500
Toxicity
mmo-esc 150 mg/L CSHSAZ 16,337,52

Chemistry & industry

Pharmacology

Metabolism/MetabolitesParaxanthine has known human metabolites that include 1,7-Dimethyluric acid and 1-Methylxanthine.；Paraxanthine is a known human metabolite of caffeine.
Tissue LocationsKidney；Liver；Placenta；Prostate
Cellular LocationsCytoplasm
Metabolite PathwaysCaffeine Metabolism

Uses & manufacturing

Use ClassificationPharmaceuticals
Applications · 5 items

DescriptionParaxanthine is an inhibitor of phosphodiesterase 9 (PDE9) and an antagonist of adenosine receptors A1 and A2 (Kis = 35 and 22 μM, respectively in equine forebrain tissues). It is the main metabolite of caffeine in humans, making up 80% of the three dimethylxanthine metabolites produced by caffeine demethylation. Paraxanthine increases locomotor activity and counteracts adenosine receptor agonist-induced motor depression in rats not habituated to caffeine. At a dose of 30 mg/kg, paraxanthine induces a significant increase in striatal cGMP and extracellular striatal dopamine concentrations in vivo. It also promotes wakefulness and increases locomotor activity and core temperature in narcoleptic transgenic mice without increasing behavioral anxiety.

Usesadenosine receptor agonist, CNS stimulant

Uses1,7-Dimethylxanthine has been used for the quantification of caffeine by high-performance liquid chromatography (HPLC).

UsesParaxanthine is an adenosine receptor ligand and a major metabolite of caffeine.This compound is a contaminant of emerging concern (CECs).

General DescriptionParaxanthine is a major plasma and urinary metabolite of caffeine. This xanthine derivative is, along with caffeine, a central nervous system stimulant. This Snap-N-Spike reference solution is applicable for caffeine quantitation in clinical toxicology or urine drug testing by LC-MS/MS or GC/MS.

Upstream & downstream products

Downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山东科立康药业有限公司053-88113608 17854192669
艾吉析科技（上海）有限公司17717235263 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 1,7-dimethylxanthine is a dimethylxanthine having the two methyl groups located at positions 1 and 7. It is a metabolite of caffeine and theobromine in animals. It has a role as a central nervous system stimulant, a human xenobiotic metabolite, a human blood serum metabolite and a mouse metabolite.

Related reactions

5 records
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Linked notes

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