5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol

Base Information

• Chemical Name: 5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol
• CAS No.: 23031-25-6
• Deprecated CAS: 46719-29-3
• Molecular Formula: C12H19NO3
• Molecular Weight: 225.288
• Hs Code.: 2942000000
• European Community (EC) Number: 245-385-8
• UNII: N8ONU3L3PG
• DSSTox Substance ID: DTXSID7021310
• Nikkaji Number: J11.466I
• Wikipedia: Terbutaline
• Wikidata: Q424340
• NCI Thesaurus Code: C61965
• RXCUI: 10368
• Pharos Ligand ID: 33ZVAS8FT45D
• Metabolomics Workbench ID: 43147
• ChEMBL ID: CHEMBL1760
• Mol file: 23031-25-6.mol

Synonyms:Benzylalcohol, a-[(tert-butylamino)methyl]-3,5-dihydroxy-(8CI);(?à)-Terbutaline;1-(3,5-Dihydroxyphenyl)-2-(tert-butylamino)ethanol;Aerodur;Brican;Bricar;Bricaril;Bricyn;Fasma;Terbutalin;

Chemical Property of 5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol

Chemical Property:

• Vapor Pressure: 3.42E-07mmHg at 25°C
• Melting Point: 204-208°C
• Refractive Index: 1.4596 (estimate)
• Boiling Point: 419.2 °C at 760 mmHg
• PKA: pKa 8.70(H2O t = 25 I = 0.01) (Uncertain);10.09(H2O t = 25 I = 0.01) (Uncertain)
• Flash Point: 165.3 °C
• PSA: 72.72000
• Density: 1.171 g/cm³
• LogP: 1.91020
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 225.13649347
• Heavy Atom Count: 16
• Complexity: 205

Purity/Quality:

99% min ^*data from raw suppliers

Terbutaline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)NCC(C1=CC(=CC(=C1)O)O)O
• Recent ClinicalTrials: Hot Flashes and Neurovascular Function in Women
• Recent EU Clinical Trials: A randomised, double-blind, double-dummy, multi-site, phase III, single dose, 4-way cross-over pharmacodynamic study evaluating the efficacy of Bricanyl Turbuhaler M3 compared to Bricanyl Turbuhaler M2 by studying the protective effect on methacholine induced bronchoconstriction in patients with stable, mild to moderate asthma
• Recent NIPH Clinical Trials: None
• Description: Terbutaline is a synthetic congener of adrenaline that acts at the β2-receptor causing bronchodilation and tocolytic effects. It was the first β2-selective adrenoreceptor agonist in general clinical use. In 2011, the Food and Drug Administration (FDA) placed a black-boxed warning on terbutaline stating that terbutaline injections should not be given to pregnant women nor should be used to prevent preterm labor or for long-term (greater than 48–72 h) treatment of preterm labor. Oral terbutaline should not be used at all due to its potential for cardiac toxicity and death. Terbutaline is on the World Anti- Doping Agency’s list of prohibited drugs for Olympic athletes (except when a Therapeutic Use Exemption has been granted in advance and when used by inhalation). Terbutaline is a short-acting β2-adrenergic receptor (β2-AR) agonist and an active metabolite of bambuterol . It binds to β1-, β2-, and β3-ARs (Ki = 31.3, 15.4, and 79.8 nM, respectively) and selectively increases adenylyl cyclase activity in CHO cell membranes expressing recombinant human β2- or β3- over β1-ARs at concentrations 100-fold greater than the respective Ki values. Terbutaline inhibits histamine release induced by ovalbumin in isolated guinea pig lung mast cells. It also inhibits airway obstruction induced by methacholine (acetyl-β-methylcholine; ) or leukotriene D4 (LTD4; ) in anesthetized guinea pigs. Formulations containing terbutaline have been used in the treatment of asthma.
• Uses: Terbutaline is used as a bronchodilator and for the prevention of premature labor. The FDA has added boxed warnings to terbutaline for its use as a tocolytic for the prevention of preterm labor. Unlabeled use includes treatment of hyperkalemia. Terbutaline is being studied for its use in treatment of certain neuromuscular disorders as well. Terbutaline is a beta-adrenoceptor agonist used to treat asthma and premature labor. Terbutaline is used for preventing and relieving bronchospasms in bronchial asthma, chronic bronchitis, pulmonary emphysema, and other broncho-pulmonary diseases.
• Indications: Terbutaline (Brethine, Bricanyl) is a relatively specific β2-adrenoceptor agonist. Terbutaline can prevent premature labor, especially in individuals who are more than 20 weeks into gestation and have no indication of ruptured fetal membranes or in whom labor is not far advanced. Its effectiveness in premature labor after 33 weeks of gestation is much less clear. Terbutaline can decrease the frequency, intensity, and duration of uterine contractions through its ability to directly stimulate β2-adrenoceptors. While it appears to be especially selective for β2-receptor activation, terbutaline does have some β1 activity as well.
• Therapeutic Function: Bronchodilator
• Clinical Use: Terbutaline should be initially used only in an appropriate hospital setting where any obstetric complications can be readily addressed. After initial administration, it can be used in the outpatient setting. Concomitant use of β2-adrenergic agonists and corticosteroids have additional diabetic effects and may rarely lead to pulmonary edema.The combination of β2- adrenergic agonists and magnesium sulfate can cause cardiac disturbances, while coadministration of terbutaline with other sympathomimetics can lead to the potentiation of the actions of the latter drugs.

Technology Process of 5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol

There total 25 articles about 5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol 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: 94.0%

C14H16O5 + tert-butylamine (75-64-9) → terbutaline (23031-25-6,37394-31-3,90877-48-8)

Guidance literature:

With sodium thiosulfate; sodium hydroxide; In ethyl acetate; at 10 ℃; for 8h; Large scale;

Reference yield: 93.2%

2-(3,5-dihydroxyphenyl)ethylene oxide + tert-butylamine (75-64-9) → terbutaline (23031-25-6,37394-31-3,90877-48-8)

Guidance literature:

With potassium tert-butylate; In toluene; at 110 ℃; Reagent/catalyst; Solvent; Temperature;

Reference yield: 92.0%

C18H24O5 + tert-butylamine (75-64-9) → terbutaline (23031-25-6,37394-31-3,90877-48-8)

Guidance literature:

With 3-tert-Butyl-4-hydroxyanisole; sodium hydroxide; In ethyl acetate; at 70 ℃; for 1h; Reagent/catalyst; Large scale;

upstream raw materials:

3,5-dihydroxyacetophenone

2-bromo-1-(3,5-dihydroxyphenyl)ethan-1-one

tert-butylamine

terbutaline hemisulfate

Downstream raw materials:

(-)-Terbutaline

(+)-Terbutaline

terbutaline hemisulfate

C₄₂H₇₀O₃₅*C₁₂H₁₉NO₃

Refernces

• 1、 -. "Preparation method of terra". Paragraph 0128-0137. . Retrieved 2021/10/05.
• 2、 -. "Method for synthesizing terbutaline". . . Retrieved 2020/02/10.