| Identification | Back Directory | [Name]
Noradrenaline | [CAS]
13460-98-5 | [Synonyms]
7-[2-[[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino]ethyl]theophyline
7-[2-[[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino]ethyl]-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione
1H-Purine-2,6-dione, 7-[2-[[2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino]ethyl]-3,7-dihydro-1,3-dimethyl- | [Molecular Formula]
C17H21N5O5 | [MDL Number]
MFCD00864193 | [MOL File]
13460-98-5.mol | [Molecular Weight]
375.38 |
| Questions And Answer | Back Directory | [Preparation]
solution of 27 g of ω-chloroacetylcatechol in 150 ml of ethanol was added dropwise over 2 hours to a stirred reflux solution of 81 g of 7-(β-aminoethyl)theophylline in 200 ml of 60% ethanol. The mixture was then boiled for 3.5 hours under nitrogen purging. The precipitate was separated by filtration, washed with water, and dried. The product was suspended in alcohol and mixed with hydrochloric acid while heating until an acid reaction was observed. After cooling, the mixture was filtered. In this manner, 37 g of 7-[β-(β'-3,4-dihydroxyphenyl-β'-oxoethylamino)ethyl]theophylline hydrochloride with a melting point of 246-249 °C was obtained. To obtain an analytically pure product, the hydrochloride was dissolved in water and precipitated with acetone. 7.1 g of 7-[β-(β'-3,4-dihydroxyphenyl-β'-oxoethylamino)ethyl]theophylline hydrochloride was dissolved in 500 ml of distilled water and hydrogenated at 48°C in the presence of 1 g of platinum oxide. When no further hydrogen absorption occurred after approximately 5 hours, the mixture was evaporated to dryness under vacuum. Purification was performed by absorbing methanol and mixing with ethyl acetate. The Theodrenaline hydrochloride crystals obtained after several days were separated by suction filtration and dried in a desiccator to give 6.1 g. |
| Chemical Properties | Back Directory | [Boiling point ]
723.6±70.0 °C(Predicted) | [density ]
1.51±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [pka]
9.59±0.10(Predicted) |
| Hazard Information | Back Directory | [Originator]
Theodrenaline,ZYF Pharm Chemical | [Definition]
ChEBI: Theodrenaline is an oxopurine. | [Manufacturing Process]
A solution of 27 g of ω-chloroacetopyrocatechol in 150 ml of ethyl alcohol is
added dropwise within 2 hours into a stirred and refluxed solution of 81 g of
7-(β-aminoethyl)theophylline in 200 ml of a 60% aqueous ethyl alcohol.
Following this, boiling is continued for another 3.5 hours while passing
through nitrogen, and the precipitated product is separated by suction
filtration, washed with water and dried. The product is suspended in alcohol,
admixed with alcoholic hydrochloric acid while heating until an acid reaction is
observed and subjected to suction filtration after cooling. Obtained in this
manner are 37 g of 7-[β-(β'-3,4-dihydroxyphenyl-β'-
oxoethylamino)ethyl]theophylline hydrochloride having a melting point of 246-
249°C. To obtain an analytically pure product, the hydrochloride is dissolved in
water and precipitated with acetone.
7.1 g of 7-[β-(β'-3,4-dihydroxyphenyl-β'-oxoethylamino)ethyl]theophylline
hydrochloride are dissolved in 500 ml of distilled water and hydrogenated at
48°C in the presence of 1 g of platinum oxide. When no further hydrogen is
absorbed after about 5 hours, the mixture is evaporated to dryness in vacuo.
Purification is effected by taking up in methyl alcohol and mixing with ethyl
acetate. Theodrenaline which has crystallized after several days is separated by suction
filtration and dried in a desiccator. A product having a melting point of 176-
178°C is obtained in amount of 6.1 g. | [Therapeutic Function]
Analeptic | [Biological Activity]
Theodrenaline is a cardiotonic agent that is also often mixed with cafedrine in a proportion to form Akrinor, which has blood pressure-lowering effects. | [in vitro]
Akrinor evokes a positive inotropic effect in human atrial trabeculae via stimulation of β-adrenoceptors (AR). | [in vivo]
Akrinor TM produces significant potentiation of FSK effects, conceivable by PDE-inhibition, only at very high, clinically irrelevant concentrations of 420 mg/L. |
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