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T1633

Sigma-Aldrich

Theophylline

anhydrous, ≥99%, powder

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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:
Molecular Weight:
180.16
Beilstein/REAXYS Number:
13463
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

grade

anhydrous

Quality Level

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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1 of 4

This Item
D0633T45001653004
vibrant-m

T1633

Theophylline

vibrant-m

D0633

7-(2,3-Dihydroxypropyl)theophylline

vibrant-m

T4500

Theobromine

vibrant-m

1653004

Theophylline

assay

≥99%

assay

-

assay

≥98.0%

assay

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

-

solubility

H2O: slightly soluble 8.3 mg/ml, alcohol: 12.5 mg/ml, 0.1 M HCl: soluble, ammonium hydroxide: soluble, diethyl ether: slightly soluble, dilute nitric acid: soluble, NH4OH: 50 mg/ml, clear, colorless, 0.1 M NaOH: soluble, dilute HCl: soluble, chloroform: soluble 9.1 mg/ml, ethanol: moderately soluble, aqueous base: soluble

solubility

-

solubility

H2O: slightly soluble, aqueous base: moderately soluble, ethanol: slightly soluble

solubility

-

color

white

color

-

color

-

color

-

originator

Forest Labs

originator

-

originator

-

originator

-

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).

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

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


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The aim of this study was to compare the main pharmacokinetic characteristics of two new paracetamol formulations, powder sachet and tablet, with that of three commercially available paracetamol formulations: two conventional solid tablets and one effervescent tablet. Twelve healthy volunteers
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Articles

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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