Paraxanthine

Catalog Number	ACM611596-1
CAS Number	611-59-6
Structure
Synonyms	1,7-Dimethylxanthine
Molecular Weight	180.16
InChI	InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)11(2)7(13)9-5/h3H,1-2H3,(H,9,13)
InChI Key	QUNWUDVFRNGTCO-UHFFFAOYSA-N
Melting Point	294-296 °C
Purity	98%+
Complexity	267
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	0
Exact Mass	180.06472551
Heavy Atom Count	13
Hydrogen Bond Acceptor Count	3
Hydrogen Bond Donor Count	1
Monoisotopic Mass	180.06472551
PhysicalState	Solid
Rotatable Bond Count	0
Topological Polar Surface Area	67.2 Ų

Case Study

The Effect Mechanism of Paraxanthine on Glutathione Synthesis

Matsumura N, et al. Journal of Pharmacological Sciences, 2023, 151(1), 37-45.

Paraxanthine is a caffeine metabolite that shares some of the same pharmacological properties as caffeine. The pharmacological activity of paraxanthine, an active metabolite of caffeine, was studied and showed that it increases intracellular glutathione levels by promoting cysteine uptake. Increasing glutathione levels is a strategy to combat neurodegenerative diseases.
Action mechanism of paraxanthine
· To investigate whether caffeine metabolites activate cysteine uptake in hippocampal slices, caffeine metabolites such as paraxanthine were applied to hippocampal slices. Experiments showed that 10 μM paraxanthine significantly increased the cysteine content, while 100 μM did not.
· To further analyze the effect of paraxanthine on GSH production in HEK293 cells, GSH was stained with CMFDA and observed by fluorescence microscopy. The results indicated that paraxanthine increases intracellular GSH levels in the presence of cysteine in HEK293 cells.
· Changes in extracellular and intracellular cysteine levels were quantified by HPLC. The results showed that paraxanthine promoted the uptake of cysteine by HEK293 cells.
· Other experimental results also showed that paraxanthine promoted cysteine uptake in SH-SY5Y cells through EAAC1 and protected SH-SY5Y cells from H2O2-induced cell damage.

Safety of Paraxanthine and Comparison with Caffeine

Matsumura, Nobuko, et al. Journal of Pharmacological Sciences, 2023, 151(1), 37-45.

Paraxanthine (1,7-dimethylxanthine) is the primary metabolite of caffeine in the human body and exhibits stimulant effects that are reminiscent of caffeine. To evaluate the toxicological properties of paraxanthines, a series of toxicological studies were conducted, including mutagenicity potential, genotoxicity, acute, subacute and subchronic oral toxicity. Research shows paraxanthine may be a safer alternative to caffeine in humans.
Safety assessment results of paraxanthine
· The results of a series of genotoxicity tests (including bacterial reverse mutation, mammalian chromosomal aberrations, and mammalian cell gene mutations) show that paraxanthine is not mutagenic.
· An LD50 of 829.20 mg/kg body weight (bw) was found for paraxanthine in the acute oral toxicity study.
· No mortality or treatment-related adverse effects were observed in the 14-day repeat dose oral toxicity study after daily oral administration of low, mid, or high doses of paraxanthine (50, 100, or 150 mg/kg bw).
· Similar results were seen in the subchronic repeat-dose 90-day oral toxicity study with daily doses up to 185 mg of paraxanthine/kg bw, with the highest dose tested determined to be the NOAEL.
· No deaths were reported with paraxanthine administration, while two animals in the high dose caffeine-treated group (185 mg/kg bw) did die.

Custom Q&A

What is another name for 1,7-DIMETHYLXANTHINE?

Paraxanthine

What is the molecular formula of Paraxanthine?

C7H8N4O2

What is the boiling point of 1,7-DIMETHYLXANTHINE?

312.97°C (rough estimate)

What is the color of Paraxanthine?

White

What is the main metabolite of caffeine in humans?

Paraxanthine

What percentage of the three dimethylxanthine metabolites produced by caffeine demethylation does Paraxanthine make up?

80%

How does Paraxanthine affect locomotor activity in rats?

It increases locomotor activity and counteracts adenosine receptor agonist-induced motor depression in rats not habituated to caffeine.

What effect does a dose of 30 mg/kg of Paraxanthine have on striatal cGMP and extracellular striatal dopamine concentrations in vivo?

It induces a significant increase in striatal cGMP and extracellular striatal dopamine concentrations.

What is the primary use of 1,7-DIMETHYLXANTHINE?

It is used as an adenosine receptor agonist and CNS stimulant.

What is the role of Paraxanthine in animals?

It is a metabolite of caffeine and theobromine in animals and acts as a central nervous system stimulant.

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