Isoproterenol

Base Information

• Chemical Name: Isoproterenol
• CAS No.: 7683-59-2
• Deprecated CAS: 149-53-1,46388-38-9,46388-38-9
• Molecular Formula: C11H17 N O3
• Molecular Weight: 211.261
• European Community (EC) Number: 231-687-7
• NSC Number: 33791,9975
• UNII: L628TT009W
• DSSTox Substance ID: DTXSID4023175
• Nikkaji Number: J28.477G
• Wikipedia: Isoprenaline
• Wikidata: Q415550
• NCI Thesaurus Code: C62041
• RXCUI: 6054
• Pharos Ligand ID: 9F2V3V2MRJAL
• Metabolomics Workbench ID: 143605
• ChEMBL ID: CHEMBL434
• Mol file: 7683-59-2.mol

Synonyms:4-(1-Hydroxy-2-((1-methylethyl)amino)ethyl)-1,2-benzenediol;Euspiran;Hydrochloride, Isoproterenol;Isadrin;Isadrine;Isoprenaline;Isopropyl Noradrenaline;Isopropylarterenol;Isopropylnoradrenaline;Isopropylnorepinephrine;Isoproterenol;Isoproterenol Hydrochloride;Isoproterenol Sulfate;Isuprel;Izadrin;Noradrenaline, Isopropyl;Norisodrine;Novodrin;Sulfate, Isoproterenol

Chemical Property of Isoproterenol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 165 - 170 C
• Refractive Index: 1.5718 (estimate)
• Boiling Point: 350.94°C (rough estimate)
• PKA: 8.64(at 25℃)
• PSA: 72.72000
• Density: 1.1240 (rough estimate)
• LogP: 1.52010
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 211.12084340
• Heavy Atom Count: 15
• Complexity: 187

Purity/Quality:

98%, ^*data from raw suppliers

4-(1-Hydroxy-2-(isopropylamino)ethyl)benzene-1,2-diol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: UN NO.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)NCC(C1=CC(=C(C=C1)O)O)O
• Recent ClinicalTrials: POTS Adrenergic Ab (CIHR Aims #1&2)
• Recent EU Clinical Trials: Pharmacological relaxation of the ureter when using access sheaths during ureterorenoscopy
• Recent NIPH Clinical Trials: A pilot study for bronchial asthma attack treatment with high flow nasal cannula therapy
• Description: Isoproterenol is a representative of the sympathomimetic drugs with high selectivity to β- adrenoreceptors. As was already noted, the addition to compounds of a bulky iso-propyl or tert-butyl group at the nitrogen atom of the β-phenylethylamino skeleton is associated with higher affinity to β-adrenergic receptive regions than to α-adrenergic. Isoproterenol is devoid of significant α-adrenergic agonistic action. Activation of β1-adrenergic receptors in the heart increases positive chronotropic and ionotropic action. Peripheral vascular resistance is increased by the widening of blood vessels, primarily in skeletal muscle, but also in renal and mesenteric blood circulation, which is caused by the β2-adrenergic system.
• Uses: Isoproterenol is used in bronchospasms, asthma, cardiac block, and shock. Isoprenaline is a potent β-agonist primarily acting at the β1-receptor. It is mainly used for the temporary emergency treatment of bradyarrhythmias. β2 effects lead to broncho- and vasodilatation, with a decrease in SVR. Isoprenaline is only available in the UK via specialist importing companies. It is administered by i.v. infusion at a dose range of 0.5–20 μg min–1.
• Indications: Isoproterenol is administered almost exclusively by inhalation from metered-dose inhalers or from nebulizers. The response to inhaled isoproterenol and other inhaled adrenomimetics is instantaneous. The action of isoproterenol is short-lived, although an objective measurement of pulmonary function has shown an effective duration of up to 3 hours. When it is administered by inhalation, the cardiac effects of isoproterenol are relatively mild, although in some cases a substantial increase in heart rate occurs.
• Clinical Use: The cardiac stimulation caused by its 1-activity andits lack of oral activity have led to its diminished use infavor of more selective -agonists. The problems have beenovercome at least partially by the design and developmentof several noncatechol selective 2-agonists. These agentsrelax smooth muscle of the bronchi, uterus, and skeletalmuscle vascular supply. They find their primary use as bronchodilatorsin the treatment of acute and chronic bronchialasthma and other obstructive pulmonary diseases. Isoproterenol is used principally by inhalation for the management of bronchospasm. It is also used intravenously for asthma and as a stimulant in cardiac arrest.

Technology Process of Isoproterenol

There total 3 articles about Isoproterenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ isoproterenol (7683-59-2)

Guidance literature:

With water; palladium; Hydrogenation;

DOI:10.1021/ja01170a044

Reference yield:

→ isoproterenol (7683-59-2)

Guidance literature:

With methanol; palladium; Hydrogenation;

Reference yield:

→ isoproterenol (7683-59-2)

Guidance literature:

DOI:10.1007/BF00908218

Downstream raw materials:

N-Isopropyl-noradrenochrom

2-(3,4-dihydroxyphenyl)-2-[(methyl)oxy]-1-(isopropylamino)ethane hydrochloride

C₁₁H₁₅NO₃

Pt(P(C₆H₅)3)2(O₂C₆H₃CH(OH)CH₂NHCH(CH₃)2)

Refernces

• 1、 -. "Pharmaceutical formula". . . Retrieved 2008/06/13.
• 2、 -. "Esters of 3-(hydroxy or hydroxymethyl)-4-hydroxyphenyl aminomethyl ketones". . . Retrieved 2008/06/13.