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T1633 Sigma

Theophylline

anhydrous, ≥99%, powder

Synonym: 1,3-Dimethylxanthine, 2,6-Dihydroxy-1,3-dimethylpurine, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione

Properties

Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Cyclic Nucleotide Metabolism,
grade   anhydrous
assay   ≥99%
form   powder
color   white
solubility   H2O: slightly soluble8.3 mg/ml
  NH4OH: soluble50 mg/ml, clear, colorless
  alcohol: soluble12.5 mg/ml
  chloroform: soluble9.1 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
Gene Information   human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140), PDE3A(5139), PDE4B(5142)
mouse ... Adora2b(11541)
rat ... Adora1(29290), Adora2a(25369), Adora2b(29316), Pde1b(29691), Pde3a(50678)

Description

Biochem/physiol Actions

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

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 cells1.

Packaging

1 kg in poly bottle

50, 100, 250 g in poly bottle

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).

Application

Theophylline has been used to study its effects on rat gene expression in the ubiquitin-proteasome pathway that regulates spermatogenesis and epididymal sperm quality1. Theophylline has also been used as an internal standard for the measurement of plasma paracetamol levels in humans2.

Price and Availability

Suggested Laboratory Gloves


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