3-Methylxanthine Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

294.33°C (rough estimate)

Density 

1.4434 (rough estimate)

refractive index 

1.6700 (estimate)

storage temp. 

2-8°C

solubility 

DMSO (Slightly, Heated), Methanol (Slightly)

form 

Solid

pka

pK1:8.10;pK2:11.3 (25°C)

color 

White to Pale Beige

Water Solubility 

Insoluble in water.

BRN 

180944

InChIKey

GMSNIKWWOQHZGF-UHFFFAOYSA-N

CAS DataBase Reference

1076-22-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,T+

Risk Statements 

22-26/27/28

Safety Statements 

22-24/25

WGK Germany 

1

RTECS 

ZD8750000

HS Code 

29335990

Toxicity

LD50 intraperitoneal in mouse: 894mg/kg

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Methylxanthine Usage And Synthesis

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].

Chemical Properties

Light yellow powder

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.

Definition

ChEBI: 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.

Biosynthesis

As the primary intermediate of theobromine degradation, 3-methylxanthine might be degraded by A. tamarii PT-7 and other candidate isolates in the liquid culture. The accumulation of 3-methylxanthine increased along with theobromine degradation since it was detected in the liquid culture after cultivation for 24?h. Over 6 days of cultivation of A. sydowii PT-2, 3-methylxanthine was produced and increased significantly (p?<?0.05) with an increasing initial theobromine concentration, respectively, showing a linear relationship between theobromine degradation and 3-methylxanthine accumulation[3].

General Description

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

Purification Methods

Crystallise it from water. [Beilstein 26 II 263, 26 III/IV 2329.]

References

[1] R. Sellman, &P. J. Klemi. “Kidney toxicity of 3-methylxanthine in the rat.” Journal of Applied Toxicology 4 6 (1984): 304–307.
[2] K. H. Algharrawi. “Direct conversion of theophylline to 3-methylxanthine by metabolically engineered E. coli.” Microbial Cell Factories 14 1 (2015).
[3] Binxing Zhou. “3-Methylxanthine production through biodegradation of theobromine by Aspergillus sydowii PT-2.” BMC Microbiology (2020): 269.

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