1,7-Dimethylxanthine Property

Melting point:

294-296 °C (lit.)

Boiling point:

312.97°C (rough estimate)

Density 

1.3640 (rough estimate)

refractive index 

1.6700 (estimate)

Flash point:

9℃

storage temp. 

room temp

solubility 

ethanol: 0.6mg/mL

form 

solid

pka

pKa 8.5 (Uncertain)

color 

white

BRN 

197907

Stability:

Store tightly sealed at RT

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)

InChIKey

QUNWUDVFRNGTCO-UHFFFAOYSA-N

SMILES

N1(C)C2=C(NC(=O)N(C)C2=O)N=C1

EPA Substance Registry System

1H-Purine-2,6-dione, 3,7-dihydro-1,7-dimethyl- (611-59-6)

Safety

Hazard Codes 

Xn,T,F

Risk Statements 

22-39/23/24/25-23/24/25-11

Safety Statements 

22-24/25-45-36/37-16-7

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

3

RTECS 

RV9380000

HS Code 

2933.59.9500

Toxicity

mmo-esc 150 mg/L CSHSAZ 16,337,52

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

1,7-Dimethylxanthine Chemical Properties,Usage,Production

Description

Paraxanthine is an inhibitor of phosphodiesterase 9 (PDE9) and an antagonist of adenosine receptors A₁ and A₂ (K_is = 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.

Chemical Properties

Off-White to Pale Yellow Solid

Uses

adenosine receptor agonist, CNS stimulant

Uses

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

Uses

1,7-Dimethylxanthine has been used for the quantification of caffeine by high-performance liquid chromatography (HPLC).

Definition

ChEBI: 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.

benefits

1,7-Dimethylxanthine (Paraxanthine) has been shown to have several of the same nootropic benefits as caffeine, including improved cognition, short-term memory, sustained attention in healthy adults and beneficial cognitive effects in animal models of Parkinson’s disease. Moreover, the beneficial impacts on physical endurance and sports performance observed with caffeine use have also been suggested for paraxanthine. Mechanistically, some of these effects are mediated by a similar mechanism for caffeine and paraxanthine, which act as antagonists of adenosine receptors A1 and A2a. Despite these similarities in mechanisms, it has been reported that there are potential differences in adenosine receptor binding affinity, as paraxanthine exhibited higher binding potencies for adenosine A1 and A2A receptors in equine forebrain and a stronger locomotor activating effect in rats relative to caffeine. Furthermore, paraxanthine, but not other methylxanthines (caffeine, theobromine, theophylline), has been shown to potentiate nitric oxide neurotransmission, which has been associated with increased blood flow and subsequent changes in aerobic exercise performance and cardiovascular health.

General Description

Paraxanthine 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.

Biochem/physiol Actions

Adenosine receptor ligand; major metabolite of caffeine

Safety Profile

An experimental teratogen. Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx.

Source

Paraxanthine (1,7-dimethylxanthine) is a metabolite of caffeine that can be found naturally in small amounts in some foods, including green coffee beans, cotyledonary leaves of Coffea arabica, Theobroma cacao fruits, roasted coffee beans, citrus flowers and Sicilian orange flower honey. However, it is predominantly found as the major metabolite of caffeine, accounting for approximately 70%–72% of ingested caffeine[1].