23031-32-5

Basic information

• Product Name: TERBUTALINE SULFATE
• Synonyms: 1-(3,5-dihydroxyphenyl)-2-tert-butylaminoethanolsulphate;3-benzenediol,5-(2-((1,1-dimethylethyl)amino)-1-hydroxyethyl)-sulfate(2;alpha-((tert-butylamino)methyl)-3,5-dihydroxybenzylalcoholsulfate(2:1)(sa;alpha-((tert-butylamino)methyl)-3,5-dihydroxy-benzylalcohosulfate(2:1);bricanyl;Bricanyl[R];2-tert-Butylamino-1-(3,5-dihydroxyphenyl)ethanol, Brethaire, Brethine, Butaliret, Monovent, Terbasmin, Terbul;TERBASMIN
• CAS NO: 23031-32-5
• Molecular Formula: 2C₁₂H₁₉NO₃*H₂O₄S
• Molecular Weight: 548.65
• EINECS: 245-386-3
• Product Categories: Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;BRETHAIRE
• Mol File: 23031-32-5.mol

Chemical Properties

• Melting Point: 246-248°C
• Boiling Point: 419.2 °C at 760 mmHg
• Flash Point: 165.3 °C
• Appearance: Crystalline Powder
• Density: 1.1840 (rough estimate)
• Vapor Pressure: 8.92E-08mmHg at 25°C
• Refractive Index: 1.6900 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: H2O: soluble100mg/mL, clear to slightly hazy, colorless to yello
• PKA: pKa1 8.8, pKa2 10.1, pKa3 11.2(at 25℃)
• CAS DataBase Reference: TERBUTALINE SULFATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERBUTALINE SULFATE(23031-32-5)
• EPA Substance Registry System: TERBUTALINE SULFATE(23031-32-5)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43-63
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DN9000000
• Hazardous Substances Data: 23031-32-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Terbutaline Sulfate is used as a bronchodilator for the treatment of asthma and other respiratory conditions. It works by relaxing the muscles in the airways and increasing airflow to the lungs, providing relief from asthma symptoms.
Used in Sports Performance Enhancement:
Terbutaline Sulfate is used as a β2-adrenergic agonist to enhance physical performance in athletes. It is known to increase the heart rate, blood pressure, and blood flow, which can improve athletic performance.
Used in Analytical and Forensic Applications:
Terbutaline (hemisulfate) is used as an analytical reference standard in forensic applications and as a general research tool for studying the effects of β2-adrenergic receptor agonists.
Used in Anti-Asthma Treatment:
Terbutaline Sulfate is used as an anti-asthmatic agent for the management of asthma symptoms. It helps in reducing inflammation and constriction of the airways, providing relief to patients suffering from asthma.

Therapeutic Function

Bronchodilator

Clinical Use

Beta2 -adrenoceptor agonist: Reversible airways obstruction

Veterinary Drugs and Treatments

Terbutaline is used as a bronchodilating agent in the adjunctive treatment of cardiopulmonary diseases (including tracheobronchitis, collapsing trachea, pulmonary edema, and allergic bronchitis) in small animals. It may be of some benefit in treating bradyarrhythmias in dogs and cats. Terbutaline has been used occasionally in horses for its bronchodilating effects, but adverse effects, short duration of activity after IV administration and poor oral absorption have limited its use. It has been shown to be useful as a diagnostic agent to diagnose anhidrosis in horses after intradermal injection. Oral and intravenous terbutaline has been used successfully in humans for the inhibition of premature labor clinical signs.

Drug interactions

Potentially hazardous interactions with other drugs Effect may be diminished by beta-blockers. Theophylline: increased risk of hypokalaemia.

Metabolism

Terbutaline undergoes extensive first-pass metabolism by sulphate (and some glucuronide) conjugation in the liver and the gut wall. It is excreted in the urine and faeces partly as the inactive sulphate conjugate and partly as unchanged terbutaline, the ratio depending upon the route by which it is given.

InChI:InChI=1/2C12H19NO3.H2O4S/c2*1-12(2,3)13-7-11(16)8-4-9(14)6-10(15)5-8;1-5(2,3)4/h2*4-6,11,13-16H,7H2,1-3H3;(H2,1,2,3,4)

Upstream product

• 51863-60-6 3,5-dihydroxyacetophenone 
• 62932-92-7 2-bromo-1-(3,5-dihydroxyphenyl)ethan-1-one 
• 23031-25-6 terbutaline 
• 14401-75-3 1-(3,5-dinitrophenyl)ethanone 
• 98-86-2 acetophenone 
• 28924-21-2 3,5-dibenzyloxyacetophenone 
• 28924-25-6 1-[3,5-bis(benzyloxy)phenyl]-2-(tert-butylamino)ethanol 

Downstream Products

• 4199-09-1 (S)-1-isopropylamino-3-(1-naphthyloxy)-2-propanol 
• 525-66-6 (R)-propranolol 
• 23031-25-6 terbutaline 
• 37394-31-3 (-)-Terbutaline 

Relevant articles and documents

Preparation method of terbutaline sulfate and B crystal form thereof

The invention relates to a preparation method of terbutaline sulfate and a B crystal form thereof, which comprises the following steps: sequentially carrying out bromination, reduction reaction and substitution reaction to obtain 1-[3, 5-bis (benzyloxy) phenyl]-2-(tert-butylamino) ethanol; reacting 1-[3, 5-di (benzyloxy) phenyl]-2-(tert-butylamino) ethanol with a reducing agent and a catalyst, performing salifying with sulfuric acid to obtain a terbutaline sulfate crude product, and crystallizing the terbutaline sulfate crude product under a heating reflux condition to obtain the terbutaline sulfate medicinal B crystal form. Raw materials and auxiliary materials used in the method are cheap and easy to obtain, highly toxic and explosive reagents are avoided in the reaction process, the whole reaction route is short, operation is easy and convenient, reaction conditions are mild and safe, the yield of the obtained finished product terbutaline sulfate and the medicinal B crystal form thereof is high, the yield of terbutaline sulfate is 83% or above, and the yield of the medicinal B crystal form is 70% or above, and industrialized production can be achieved easily.

Preparation method of terbutaline sulfate

The invention relates to the field of preparation of chemicals, in particular to a preparation method of terbutaline sulfate. The invention provides a preparation method of terbutaline sulfate. With simple and low-cost acetophenone as an initial raw material, the terbutaline is prepared through five-step reaction; then the terbutaline is subjected to salifying and purification to obtain terbutaline sulfate. According to the method disclosed by the invention, the total synthesis route of terbutaline is effectively shortened, so that the method is simple in intermediate purification, single in reaction solvent, simple in process, mild in reaction condition, easy to operate, high in total yield and more suitable for industrial production; the burden of workshop waste liquid treatment and purification is relieved, the three wastes and reaction energy consumption are reduced, the whole route is combined, research and control of raw material medicine impurities are better facilitated, and working hours are shortened technically and the three wastes and reaction energy consumption are reduced technically.

Preparation method of terbutaline sulfate

The invention discloses a preparation method of terbutaline sulfate, wherein the method comprises the following steps: carrying out a bromination reaction on 3,5-dihydroxyacetophenone as a raw material by using a bromination reagent without hydroxyl protection, carrying out reduction and ring closing, carrying out a ring-opening reaction with tert-butylamine, and finally forming a salt with sulfuric acid to obtain terbutaline sulfate. According to the method, the defects of requirement of deprotection after hydroxyl protection, use of various high-risk highly toxic reagents, long reaction stepand low yield in the prior art are overcome.