Introduction：Basic information about Orciprenaline CAS 586-06-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Orciprenaline Basic information
| Product Name: | Orciprenaline |
| Synonyms: | 5-[1-hydroxy-2-(1-methylethylamino)ethyl]benzene-1,3-diol;5-(1-hydroxy-2-propan-2-ylamino-ethyl)benzene-1,3-diol;orciprenaline;1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanol;1,3-Benzenediol, 5-1-hydroxy-2-(1-methylethyl)aminoethyl-;1,3-Benzenediol, 5-[1-hydroxy-2-[(1-methylethyl)amino]ethyl]- (9CI);3,5-Dihydroxy-a-[(isopropylamino)methyl]benzyl alcohol;Benzyl alcohol, 3,5-dihydroxy-a-[(isopropylamino)methyl]- (6CI, 8CI) |
| CAS: | 586-06-1 |
| MF: | C11H17NO3 |
| MW: | 211.26 |
| EINECS: | 2095691 |
| Product Categories: | Orciprenaline |
| Mol File: | 586-06-1.mol |
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Orciprenaline Chemical Properties
| Melting point | 100° |
| Boiling point | 350.94°C (rough estimate) |
| density | 1.1240 (rough estimate) |
| refractive index | 1.5718 (estimate) |
| pka | 9.11±0.10(Predicted) |
| CAS DataBase Reference | 586-06-1(CAS DataBase Reference) |
Safety Information
Orciprenaline Usage And Synthesis
| Chemical Properties | Melting point: 100°C. Its sulfuric acid ([5874-97-5]) has a melting point of 202-203°C. |
| Originator | Alupent, Boehringer Ingelheim ,W. Germany ,1961 |
| Uses | Bronchodilator. |
| Definition | ChEBI: Metaproterenol is a member of phenylethanolamines. |
| Manufacturing Process | In an initial operation, 3,5-diacetoxyacetophenone was reacted first withbromine and then with isopropylamine to give 1-(3,5-dihydroxyphenyl)-2-isopropylaminoethanone.
59 g of 1-(3,5-dihydroxy-phenyl)-2-isopropylaminoethanone (free base) weredissolved in 590 cc of methanol, and the solution was hydrogenated in thepresence of about 80 g Raney nickel at room temperature and under apressure of 5 atm. Hydrogen absorption was terminated after a few minutes.The catalyst was separated by vacuum filtration, and the filtrate, an ethanolicsolution of 1-(3,5-dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethane, wasadmixed with the calculated amount of an alcoholic 20% sulfuric acid solution.A crystalline precipitate formed which was filtered off and washed withalcohol. For purification, the product was dissolved in water and the solutionwas filtered through iron-free charcoal.
Thereafter, the filtrate was evaporated to dryness in vacuo and the residuewas taken up in alcohol. The crystalline precipitate which separated out aftersome standing was separated by vacuum filtration and washed with alcohol.After recrystallization from 90% alcohol, 61 g (83.2% of theory) of 1-(3,5-dihydroxyphenyl)-1-hydroxy-2-isopropylamino-ethane sulfate, MP 202° to203°C, was obtained. |
| Therapeutic Function | Bronchodilator |
| Clinical Use | Metaproterenol was the first β-sympathomimetic drug with metabolic stabilityto achieve wide clinical use. |
Orciprenaline Preparation Products And Raw materials
| Raw materials | Acetone-->Isopropylamine-->Hydrogen |
