Theophylline
SIGMA/T1633 - anhydrous, ≥99%, powder
Synonym: 1,3-Dimethylxanthine; 2,6-
CAS Number: 58-55-9
Empirical Formula (Hill Notation): C7H8N4O2
Molecular Weight: 180.16
EC Number: 200-385-7
MDL Number: MFCD00079619
Linear Formula: C7H8N4O2
Product Type: Chemical
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: T1633-50G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: T1633-100G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: T1633-250G
This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: T1633-1KG
| assay | ≥99% |
| color | white |
| form | powder |
| grade | anhydrous |
| InChI | 1S/C7H8N4O2/c1-10-5-4(8-3 |
| InChI key | ZFXYFBGIUFBOJW-UHFFFAOYSA |
| originator | Forest Labs |
| Quality Level | 200  |
| SMILES string | CN1C(=O)N(C)c2[nH]cnc2C1= |
| solubility | 0.1 M HCl: soluble |
| 0.1 M NaOH: soluble | |
| alcohol: 12.5 mg/ml | |
| ammonium hydroxide: soluble | |
| aqueous base: soluble | |
| chloroform: soluble 9.1 mg/ml | |
| diethyl ether: slightly soluble | |
| dilute HCl: soluble | |
| dilute nitric acid: soluble | |
| ethanol: moderately soluble | |
| H2O: slightly soluble 8.3 mg/ml | |
| NH4OH: 50 mg/ml, clear, colorless |
| 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: | Phosphodiesterase inhibitor; diuretic; cardiac stimulant; muscle relaxant; asthma medication. |
| 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. |
| 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 . |
| 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 . |
| Features and Benefits: | This compound was developed by Forest Labs . To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here . |
| Packaging: | 1 kg in poly bottle |
| Packaging: | 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-dihy |
| Symbol |  GHS06 |
| Signal word | Danger |
| Hazard statements | H301 |
| Precautionary statements | P264 - P270 - P301 + P310 - P405 - P501 |
| Hazard Codes | Xn |
| Risk Statements | 22 |
| RIDADR | UN 2811 6.1 / PGIII |
| WGK Germany | WGK 1 |
| Flash Point(F) | Not applicable |
| Flash Point(C) | Not applicable |
| Purity | ≥99% |
| UNSPSC | 41106305 |