T1633

Theophylline

≥99% (HPLC), powder, phosphodiesterase inhibitor

• Synonym(s): 1,3-Dimethylxanthine, 2,6-Dihydroxy-1,3-dimethylpurine, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione
• Empirical Formula (Hill Notation): C₇H₈N₄O₂
• CAS Number: 58-55-9
• Molecular Weight: 180.16
• Beilstein/REAXYS Number: 13463
• EC Number: 200-385-7
• MDL number: MFCD00079619
• UNSPSC Code: 41106305
• PubChem Substance ID: 24277677
• NACRES: NA.77

Properties

• product name: Theophylline, anhydrous, ≥99%, powder
• grade: anhydrous
• Quality Level: 200
• assay: ≥99%
• form: powder
• color: white
• solubility: H₂O: slightly soluble 8.3 mg/ml; NH₄OH: 50 mg/ml, clear, colorless; alcohol: 12.5 mg/ml; chloroform: soluble 9.1 mg/ml; 0.1 M HCl: soluble; 0.1 M NaOH: soluble; ammonium hydroxide: soluble; aqueous base: soluble; diethyl ether: slightly soluble; dilute HCl: soluble; dilute nitric acid: soluble; ethanol: moderately soluble
• originator: Forest Labs
• SMILES string: CN1C(=O)N(C)c2[nH]cnc2C1=O
• InChI: 1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
• Inchi Key: ZFXYFBGIUFBOJW-UHFFFAOYSA-N
• Gene Information: human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140) , PDE3A(5139) , PDE3B(5140) , PDE4A(5141) , PDE4B(5142) , PDE4C(5143) , PDE4D(5144) ; mouse ... Adora2b(11541) ; rat ... Adora1(29290) , Adora2a(25369) , Adora2b(29316) , Pde1b(29691) , Pde3a(50678)

Description

Application

Theophylline has been used to study its effects on rat gene expression in the ubiquitin-proteasome pathway that regulates spermatogenesis and epididymal sperm quality. Theophylline has also been used as an internal standard for the measurement of plasma paracetamol levels in humans.

Biochem/physiol Actions

Theophylline is a tea alkaloid that functions as a nonselective PDE4 inhibitor. It can induce smooth muscle relaxation in the bronchiolae of asthma patients. At increased concentrations, theophylline can function as a reprotoxic agent and can cause infertility by incapacitating Sertoli cells. This subsequently causes the premature release of late differentiating spermatogenic cells.

Phosphodiesterase inhibitor; diuretic; cardiac stimulant; muscle relaxant; asthma medication.

Features and Benefits

This compound is a featured product for ADME Tox and Cyclic Nucleotide research. Discover more featured ADME Tox and Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Adenosine Receptors and Phosphodiesterases pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Forest Labs. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Theophylline dissolves in 1 M NH4OH at 50 mg/ml to yield a clear, colorless solution. It is soluble in 0.1 M HCl, 0.1 M NaOH and is slightly soluble(8.3 mg/ml) in water. It is also moderately soluble in ethanol. Furthermore, it is soluble in alcohol (12.5 mg/ml), and chloroform (9.1 mg/ml), alkali hydroxides, ammonia, dilute hydrochloric or nitric acid, but is sparingly soluble in ether.

The solubility of the methylxanthines is low, but can be enhanced by the formation of complexes (usually 1:1) with a wide variety of compounds such as ethylenediamine (to form aminophylline). The formation of complex double salts (caffeine and sodium benzoate) or true salts (like choline theophyllinate, and oxtriphylline) also improves aqueous solubility. These salts or complexes dissociate to yield the parent methylxanthines when dissolved in biological fluids and should not be confused with covalently modified derivatives such asdyphylline (1,3-dimethyl-7-(2,3-dihydroxypropyl)-xanthine).

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301,H360D
• pcodes: P202 - P264 - P280 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral - Repr. 1B
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves