Introduction：Basic information about Orciprenaline sulfate CAS 5874-97-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Orciprenaline sulfate Basic information
| Product Name: | Orciprenaline sulfate |
| Synonyms: | 1-(3,5-dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethanesulfate;1-(3,5-dihydroxyphenyl)-2-(isopropylamino)ethanolsulfate;3,5-dihydroxy-alpha-((isopropylamino)methyl)benzylalcoholsulfate;3,5-dihydroxy-alpha-((isopropylamino)methyl)-benzylalcohosulfate(2:1)(s;3-benzenediol,5-(1-hydroxy-2-((1-methylethyl)amino)ethyl)-sulfate(2:1);alotec;metaprel;novasmasol |
| CAS: | 5874-97-5 |
| MF: | C22H36N2O10S |
| MW: | 520.59 |
| EINECS: | 227-539-6 |
| Product Categories: | Adrenergics;Agonists;Neurotransmitters;Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;5874-97-5 |
| Mol File: | 5874-97-5.mol |
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Orciprenaline sulfate Chemical Properties
| Melting point | 202-203° |
| storage temp. | 2-8°C |
| solubility | Freely soluble in water, slightly soluble in ethanol (96 per cent), practically insoluble in methylene chloride. |
| form | Solid |
| color | White to Off-White |
| Stability: | Hygroscopic |
| Major Application | pharmaceutical (small molecule) |
| InChI | 1S/2C11H17NO3.H2O4S/c2*1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8;1-5(2,3)4/h2*3-5,7,11-15H,6H2,1-2H3;(H2,1,2,3,4) |
| InChIKey | MKFFGUZYVNDHIH-UHFFFAOYSA-N |
| SMILES | OS(O)(=O)=O.CC(C)NCC(O)c1cc(O)cc(O)c1.CC(C)NCC(O)c2cc(O)cc(O)c2 |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 20 |
| Safety Statements | 36 |
| WGK Germany | 2 |
| RTECS | DO2275000 |
| HS Code | 2922504500 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Inhalation |
| Toxicity | LD50 in rats (mg/kg): 42 orally (Goldenthal) |
Orciprenaline sulfate Usage And Synthesis
| Chemical Properties | White or almost white, slightly hygroscopic, crystalline powder. |
| Originator | Alupent, Boehringer Ingelheim ,W. Germany ,1961 |
| Uses | Beta2-adrenoceptor agonist; bronchodilator. |
| Uses | Bronchodilatator;Beta-adrenergic agonist |
| 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. |
| Brand name | Alupent (Boehringer Ingelheim); Prometa (Muro). |
| Therapeutic Function | Bronchodilator |
| Pharmacokinetics | Metaproterenol is a direct-acting resorcinol analogue of isoproterenol. The N-isopropyl isβ-directing, and the combination with the resorcinol ring system enhances the selectivity for theβ2-receptors. It is the least potent of the β2-selective agonists, however, most likely because ofthe poor β2-selectivity of the isopropyl group. It has good oral bioavailability being resistant toCOMT and only slowly metabolized by MAO. When administered orally, it has an onset ofapproximately 30 minutes with a 4-hour duration. Inhaled metaproterenol can have an onset asquick as 5 minutes; however, it can be as long as 30 minutes in susceptible individuals.Metaproterenol is available in tablet, syrup, and inhalation dosage forms and is recommended forbronchial asthma attacks and treatment of acute asthmatic attacks in children 6 years of age andolder (5% solution for inhalation only). Metaproterenol has the same adverse effect profile asother adrenergic agonists, but with a decreased incidence of arrhythmias. |
Orciprenaline sulfate Preparation Products And Raw materials
| Raw materials | Isopropylamine-->Hydrogen |
