5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol
- CAS No.
- 23031-25-6
- Chemical Name:
- 5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol
- Synonyms
- Terbutaline;Bambuterol EP Impurity A;C07129;Terbutaline-d3;Tibolone Impurity 19;CarButerol impurity A;Bambuterol impurity 1;Carbuterol Impurity 1;Terbutaline Impurity 29;Terbutaline Impurity 36
- CBNumber:
- CB02131227
- Molecular Formula:
- C12H19NO3
- Molecular Weight:
- 225.28
- MOL File:
- 23031-25-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/3/18 13:30:28
| Melting point | 119-122° |
|---|---|
| Boiling point | 366.8°C (rough estimate) |
| Density | 1.0951 (rough estimate) |
| refractive index | 1.4596 (estimate) |
| storage temp. | Refrigerator |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| form | Solid |
| pka | pKa 8.70(H2O t = 25 I = 0.01) (Uncertain);10.09(H2O t = 25 I = 0.01) (Uncertain) |
| color | White to Off-White |
| CAS DataBase Reference | 23031-25-6 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS08 |
|---|---|
| Signal word | Warning |
| Hazard statements | H373-H361 |
| Precautionary statements | P260-P314-P501-P201-P202-P281-P308+P313-P405-P501 |
5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol Chemical Properties,Uses,Production
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).
Uses
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.
Definition
ChEBI: A member of the class of phenylethanolamines that is catechol substuted at position 5 by a 2-(tert-butylamino)-1-hydroxyethyl group.
Mechanism of action
Terbutaline is a synthetic sympathomimetic amine. It is one of the most selective direct–acting stimulants of β2-adrenoreceptors. It stimulates smooth muscle β2-adrenoreceptors in the bronchi, relaxing them and relatively minutely acting on the β1—receptors of the heart.
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.
Side effects
Terbutaline is frequently used in the management of premature labor, although it has not been marketed for such use. Its effectiveness, side effects, precautions, and contraindications are similar to those of all β2-adrenergic agonists. Terbutaline can cause tachycardia, hypotension, hyperglycemia, and hypokalemia. It can be given orally in addition to subcutaneous or intravenous administration.
Environmental Fate
Terbutaline is administered as the sulfate. It is a white to graywhite,
crystalline powder; nearly odorless or with the faint odor
of acetic acid. Terbutaline has a slightly bitter taste. It has
a melting point of 247°C. Terbutaline sulfate is soluble at 1 g
per 1.5 ml water or 250 ml of ethanol. It is soluble in 0.1 N
hydrochloric acid, slightly soluble in methanol, and insoluble
in chloroform. While terbutaline is stable under normal
conditions as a solid, it is unstable in light. Terbutaline is
degraded through oxidative processes; this is enhanced in the
presence of trace levels of metals and in the presence of oxygen.
No information is currently available on breakdown in soil,
groundwater, or surface water.
5-(1-Hydroxy-2-tert-butylamino-ethyl)benzene-1,3-diol Preparation Products And Raw materials
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