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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

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Properties

Related Categories Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
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
originator   Forest Labs
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 cells.

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 quality. Theophylline has also been used as an internal standard for the measurement of plasma paracetamol levels in humans.

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

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Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
1
RTECS 
XH3850000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

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Discover Bioactive Small Molecules for Cytokines & Growth Factors Research

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MSMLS Online Plate Map

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Peer-Reviewed Papers
15

References

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