13460-98-5

Basic information

• Product Name: Noradrenaline
• Synonyms: 7-[2-[[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino]ethyl]-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione;7-[2-[[2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl]amino]ethyl]theophyline
• CAS NO: 13460-98-5
• Molecular Formula: C₁₇H₂₁N₅O₅
• Molecular Weight: 375.38
• EINECS: 219-920-0
• Mol File: 13460-98-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 723.6°Cat760mmHg
• Flash Point: 391.4°C
• Appearance: /
• Density: 1.51g/cm³
• Vapor Pressure: 5.61E-22mmHg at 25°C
• Refractive Index: 1.696
• PKA: 9.59±0.10(Predicted)
• CAS DataBase Reference: Noradrenaline(CAS DataBase Reference)
• NIST Chemistry Reference: Noradrenaline(13460-98-5)
• EPA Substance Registry System: Noradrenaline(13460-98-5)

Safety Data

• Hazardous Substances Data: 13460-98-5(Hazardous Substances Data)

Usage

Originator

Theodrenaline,ZYF Pharm Chemical

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.

InChI:InChI=1/C17H21N5O5/c1-20-15-14(16(26)21(2)17(20)27)22(9-19-15)6-5-18-8-13(25)10-3-4-11(23)12(24)7-10/h3-4,7,9,13,18,23-25H,5-6,8H2,1-2H3

Relevant articles and documents

Process for the production of basic substituted alkyl theophylline

Basic substituted alkyl theophylline derivatives of the formula STR1 in which Alk is a straight or branched chain alkylene group with 2 to 4 carbon atoms and R is hydrogen or a methyl group are produced by catalytic hydrogenation of compounds of the formula STR2 where the phenolic hydroxyl groups and/or the secondary basic nitrogen atom can contain protective groups using as the solvent a compound of the formula STR3 where R', R" and R'" are the same or different and are alkyl groups of 1 to 2 carbon atoms and R' together with R'" can also be an alkylene bridge with 3 to 4 carbon atoms and in a given case the protective groups present are split off.