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T1633

Sigma-Aldrich

Theophylline

anhydrous, ≥99%, powder

Synonym(s):
1,3-Dimethylxanthine, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, 2,6-Dihydroxy-1,3-dimethylpurine
Empirical Formula (Hill Notation):
C7H8N4O2
CAS Number:
Molecular Weight:
180.16
Beilstein:
13463
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

grade

anhydrous

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

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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.

Packaging

50, 100, 250 g in poly bottle
1 kg in poly bottle

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 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 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 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).

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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