7-(2-Chloroethyl)Theophylline
[CAS# 5878-61-5]

Identification

• Classification: Biochemical >> Inhibitor >> G protein coupled receptor(GPCR & G Protein)
• Name: 7-(2-Chloroethyl)Theophylline
• Synonyms: 7-(2-Chloroethyl)-1,3-Dimethyl-Purine-2,6-Dione; 7-(2-Chloroethyl)-1,3-Dimethyl-Xanthine; Kbioss_002446
• Molecular Formula: C₉H₁₁ClN₄O₂
• Molecular Weight: 242.66
• CAS Registry Number: 5878-61-5
• EC Number: 227-553-2
• SMILES: CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CCCl

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.672, Calc.^*
• Boiling Point: 459.8±51.0 ºC (760 mmHg), Calc.^*
• Flash Point: 231.9±30.4 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

7-(2-Chloroethyl)theophylline is a derivative of the xanthine alkaloid theophylline, which is well known for its bronchodilator and stimulant properties. The modification at the 7-position with a chloroethyl group alters its chemical properties and potential applications compared to the parent theophylline structure. The synthesis of 7-(2-Chloroethyl)theophylline has been documented in the chemical literature, typically involving the selective alkylation of theophylline with appropriate chloroethylating agents under controlled conditions.

Theophylline and its derivatives, including 7-(2-Chloroethyl)theophylline, have been studied for their pharmacological activities. The introduction of a chloroethyl group can influence the solubility, reactivity, and biological interactions of the compound. Such modifications have been explored in medicinal chemistry to investigate the structure-activity relationships of xanthine-based molecules.

7-(2-Chloroethyl)theophylline has been examined in chemical and pharmaceutical research as a potential intermediate in the synthesis of bioactive compounds. Its chemical reactivity, particularly due to the presence of the chloroethyl functional group, allows it to participate in further transformations that can lead to the development of other xanthine-based derivatives.

While theophylline itself has well-established applications in the treatment of respiratory conditions such as asthma and chronic obstructive pulmonary disease, specific applications of 7-(2-Chloroethyl)theophylline have been less widely reported. However, its structural modifications make it a subject of interest in research aimed at developing xanthine derivatives with altered pharmacokinetic and pharmacodynamic properties.

The discovery and study of 7-(2-Chloroethyl)theophylline contribute to the broader understanding of xanthine chemistry and its potential applications in pharmaceutical and chemical research. Its documented synthesis and chemical behavior highlight its role as a modified theophylline derivative with possible utility in specialized applications.

References

2004. Synthesis of molecularly imprinted polymer with 7-chloroethyl-theophylline-immobilized silica gel as template and its molecular recognition function. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 60(1-2).
DOI: 10.1016/s1386-1425(03)00225-7

1989. Psychomotor-stimulant effects of 3-isobutyl-1-methylxanthine: Comparison with caffeine and 7-(2-chloroethyl) theophylline. European Journal of Pharmacology, 170(1-2).
DOI: 10.1016/0014-2999(89)90130-1

1986. Analogues of caffeine and theophylline: effect of structural alterations on affinity at adenosine receptors. Journal of Medicinal Chemistry, 29(7).
DOI: 10.1021/jm00157a035