(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Names and Identifiers
Name | (R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride
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Synonyms | Aerolone Aerotrol proternol Proternol Isoproterenol HCl Isoprenaline chloride norisodrinehydrochloride Isoetharine Hydrochloride dl-Isadrine hydrochloride Isoprenaline hydrochloride ISOPROTERENOL HYDROCHLORIDE Isoproterenol Hydrochloride (+-)-Isoprenaline hydrochloride (+-)-Isoproterenol hydrochloride (+-)-sopropylnoradrenaline hydrochloride N-ISOPROPYL-DL-NORADRENALINE HYDROCHLORIDE alpha-(isopropylaminomethyl)-3,4-dihydroxybenzylalcoholhydrochloride 3,4-dihydroxy-alpha-((isopropylamino)methyl)-benzylalcohohydrochloride 2-benzenediol,4-(1-hydroxy-2-((1-methylethyl)amino)ethyl)-hydrochloride 3,4-Dihydroxy-alpha-((isopropylamino)methyl)benzyl alcohol hydrochloride ,2-Benzenediol, 4-(1-hydroxy-2-((1-methylethyl)amino)ethyl)-, hydrochloride (R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride
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CAS | 51-30-9 2576-92-3 50-96-4
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EINECS | 200-089-8 |
InChI | InChI=1/C11H17NO3.ClH/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8;/h3-5,7,11-15H,6H2,1-2H3;1H/p-1 |
InChIKey | IROWCYIEJAOFOW-UHFFFAOYSA-N |
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Physico-chemical Properties
Molecular Formula | C11H18ClNO3
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Molar Mass | 247.72 |
Density | 1.2296 (rough estimate) |
Melting Point | 165-175°C (dec.)(lit.) |
Boling Point | 192°C (rough estimate) |
Water Solubility | Soluble |
Solubility | DMSO 50 mg/mL Water 50 mg/mL Ethanol <1 mg/mL |
Appearance | White crystalline powder |
Color | White to Off-White |
BRN | 3917363 |
Storage Condition | 2-8°C |
Stability | Stable, but may be air and light sensitive. Incompatible with strong oxidizing agents. |
Sensitive | Air and light sensitivity |
Refractive Index | 1.6000 (estimate) |
MDL | MFCD00012603 |
Use | Suitable for the treatment of bronchial asthma attacks, but also for chronic emphysema |
In vitro study | In intact rat adipocytes, Isoprenaline(300 nM,3 min) increased granule cGMP-and cilostamide-inhibition, low-Km cAMP phosphodiesterase (PDE of cAMP) activity by about 100%. Isoprenaline inhibits insulin-stimulated glucose transport activity in rat adipocytes. Isoprenaline promotes a time-dependent decrease in the accessibility (t1/2 approximately 2 min) of insulin-stimulated cell surface GLUT4 by> 50% in the absence of adenosine, this directly correlates with the observed inhibition of transport activity. Isoprenaline(5 nM and 10 mM) increases the level of cyclic AMP, and Cilostamide(10 mM), a specific PDE (phosphodiesterase 4) inhibitor of cyclic AMP rolipram(10 mM) and ring GMP lifters (50 nM ANF or 30 nMSNP plus 100 nM DMPPO) to enhance this effect. Isoprenaline increased the transcriptional activity of the GIα-2 gene by 140 compared with the control, while the Gsα gene-specific hybridization remained unchanged. Isoprenaline(20 nM) increases the amplitude of total iK and causes a negative shift of the activation curve of IK by about 10 mV, blocking the L-type calcium current regardless of the presence or absence of 300 nM nisoldipine. In rabbit ex vivo pacemaker cells, Isoprenaline(20 nM) increased the spontaneous pacemaker rate in sinoatrial node pacemaker cells by 16%. |
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Risk and Safety
Hazard Symbols | Xi - Irritant
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Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin.
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Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36 - Wear suitable protective clothing.
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WGK Germany | 2 |
RTECS | DO1925000 |
FLUKA BRAND F CODES | 3-8-10 |
HS Code | 29225090 |
Toxicity | LD50 oral in rabbit: 3070mg/kg |
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Reference
Reference Show more | 1. Jia Chenglin, Cui, jingangwang, Peiwei et al. Effect of Apocynin on prevention of isoproterenol-induced paroxysmal atrial fibrillation in mice [J]. Journal of Integrated Traditional Chinese and Western medicine, cardiovascular and cerebrovascular diseases 2019 17(06):842-846. 2. Qian Zhili Deng Lin red Ouyang star. Effects of type Ⅰ collagen and isoproterenol on the formation of branching structure of rat airway smooth muscle cells in three-dimensional culture [J]. Biomedical engineering research 2019. 3. Jia Chenglin, Chen Yu, Zhang Teng. Mechanism of Panax notoginseng saponins in prevention of isoproterenol-induced paroxysmal atrial fibrillation in mice [J]. Journal of Integrated Traditional Chinese and Western medicine, cardiovascular and cerebrovascular diseases, 2018, 16(003):291-295. 4. He Tianzhu, Xin Yu, Song Yan, et al. Protective effect of Salvia miltiorrhiza-sandalwood extract on myocardial ischemia injury induced by isoproterenol in mice [J]. Journal of Jilin Agricultural University, 2019, 41(02):70-76. 5. Qin, Yan, Yang, Shan, Zhang, Nan, et al. Protective effect of Salvia miltiorrhiza extract on tumor complicated with myocardial ischemia injury [J]. Journal of Hebei Medical University 40(6). 6. Yao, Hong, et al. "A strategy for integrated pharmacokinetic study of cardiovascular herbal medicines based on chemiluminescence and HPLC-MS/MS assays: a case using Danshen injection." RSC advances 7.22 (2017): 13570-13583. 7. [IF=3.361] Hong Yao et al."A strategy for integrated pharmacokinetic study of cardiovascular herbal medicines based on chemiluminescence and HPLC-MS/MS assays: a case using Danshen injection."Rsc Adv. 2017 Feb;7(22):13570-13583 8. [IF=5.81] Lihong Zhang et al."An Integrative Pharmacology-Based Strategy to Uncover the Mechanism of Xiong-Pi-Fang in Treating Coronary Heart Disease with Depression."Front Pharmacol. 2021; 12: 590602 9. [IF=4.451] Yue Liu et al."Polyphenol-rich fraction from Thymus quinquelostatus Celak attenuates the myocardial ischemia injury in mice induced by isoproterenol through inhibiting apoptosis, antioxidation and activating PI3K/AKT pathway."J Funct Foods. 2021 Dec;87:10 10. [IF=3.361] Jianyong Huang et al."An integrated pharmacokinetic study of Dengzhanxixin injection in rats by combination of multicomponent pharmacokinetics and anti-myocardial ischemic assay."Rsc Adv. 2019 Aug;9(44):25309-25317 |
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Standard
Authoritative Data Verified Data
This product is 4-[(2-isopropylamino-1-hydroxy) ethyl]-1, 2-benzenediol hydrochloride. The content of C11H17N03 • HC1 shall not be less than 98.5% calculated on a dry basis.
Last Update:2024-01-02 23:10:35
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Trait
Authoritative Data Verified Data
- This product is white or white crystalline powder; Odorless; Light and air in the situation of gradual color change, in alkaline solution easier to change color.
- This product is soluble in water, slightly soluble in ethanol, insoluble in chloroform or ether.
melting point
The melting point of this product (General rule 0612) is 165.5~170°C, and it is decomposed at the same time during melting.
Last Update:2022-01-01 15:04:25
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Differential diagnosis
Authoritative Data Verified Data
- take about 20mg of this product, add 2ml of water to dissolve, add 2 drops of ferric chloride test solution, that is dark green; Drop the new 5% sodium bicarbonate solution, that is, turn blue, then turn red.
- take about 10 mg of this product, Add 10ml of water to dissolve, take 2ml of solution, add hydrochloric acid titration solution (0.lmol/L)0.1, plus 0.1 mol/L iodine solution 1ml, 5 minutes, add 0.lmol/L sodium thiosulfate solution 4ml, that is light red.
- take this product, add water to make a solution containing about 50ug per lml, according to UV-visible spectrophotometry (General 0401), there is maximum absorption at the wavelength of 280nm, the absorbance was about 0.50.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 349).
- the aqueous solution of this product was chloride identification (1) of the reaction (General 0301).
Last Update:2022-01-01 15:04:25
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Exam
Authoritative Data Verified Data
acidity
take 0.10g of this product, Add 10ml of water to dissolve, and measure according to law (General rule 0631). The pH value should be 4.5~5.5.
Related substances
take this product, add mobile phase to dissolve and dilute to make a solution containing about 5mg per lml as a test solution; Take 1ml for precision measurement and put it in a 200ml measuring flask, dilute to the scale with the mobile phase, shake, and serve as a control solution. Separately, the appropriate amounts of the reference substance and the isoprenaline hydrochloride were dissolved and diluted with the mobile phase to prepare a mixed solution containing about 1.25ug in each 1 ml, which was used as the system applicable solution. According to the test of high performance liquid chromatography (General rule 0512), silica gel bonded with eighteen alkyl silane was used as filler; Phosphoric acid solution (11.5g of phosphoric acid was taken, dissolved in water and diluted to ML)-methanol (95:5) as mobile phase; The detection wavelength was 280mn. Take the system applicable solution 20 u1 and inject it into the liquid chromatograph. The resolution between the peak of isoprenaline and the peak of isoprenaline should be greater than 3.0, and the signal-to-noise ratio of the peak of isoprenaline should be greater than 3. 20ul of the test solution and the control solution were respectively injected into the liquid chromatograph, and the chromatogram was recorded to 7 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.5%), the sum of each impurity peak area shall not be greater than 2 times (1.0%) of the main peak area of the control solution.
loss on drying
take this product, dry to constant weight at 80°C, weight loss shall not exceed 0.5% (General rule 0831).
ignition residue
not more than 0.1% (General rule 0841).
Last Update:2022-01-01 15:04:26
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Content determination
Authoritative Data Verified Data
take about 0.15g of this product, precision weighing, add 30ml of glacial acetic acid, slightly warm to dissolve, cool, add 5ml of Mercury acetate test solution and 1 drop of crystal violet indicator solution, with perchloric acid titration solution (0.1 mol/L) titration to a blue color of the solution, and the results of the titration were corrected by a blank test. Each l of perchloric acid titrant (0.1 mol/L) corresponds to 24.77mg of C11H17NO3. HCI.
Last Update:2022-01-01 15:04:27
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Category
Authoritative Data Verified Data
Last Update:2022-01-01 15:04:27
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Storage
Authoritative Data Verified Data
light-shielded, sealed, and stored in a dry place.
Last Update:2022-01-01 15:04:27
(R,*)-()-4-[1-hydroxy-2-[(1-methylethyl)amino]butyl]pyrocatechol hydrochloride - Isoprenaline Hydrochloride Injection
Authoritative Data Verified Data
This product is a sterile aqueous solution of isoprenaline hydrochloride. Containing isoprenaline hydrochloride (C11H17N03 • HC1) shall be between 85.0% and 110.0% of the labeled amount.
trait
This product is a clear colorless liquid.
identification
- take 2ml of this product, add 2 drops of ferric chloride test solution, which is dark green; Add a new 5% sodium bicarbonate solution, which turns blue; Then turn red.
- take this product and isoprenaline hydrochloride reference, respectively, plus 80% methanol to make a solution containing about 0.2mg of isoprenaline hydrochloride per 1 ml. According to the thin layer chromatography (General 0502) test, absorb the above two solutions of each L01, respectively, on the same silica gel thin layer plate, with ethyl acetate-isopropanol-water-concentrated ammonia solution (50:30:16:4) for the development of the solvent, expand, dry, placed in saturated diethylamine vapor for a few minutes, sprayed with diazonium p-nitroaniline test solution, the position and color of the main spot displayed by the test article should be the same as the main spot of the control article.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
examination
- the pH value should be 2.5 to 4.5 (General 0631).
- Related substances take this product as a test solution; Take 1ml for precision measurement, put it in a 0.1% volumetric flask, dilute it to the mark with sodium metabisulfite solution, shake well, and use it as a control solution. According to the chromatographic conditions under the content determination item, respectively inject the sample solution and the control solution respectively into the liquid chromatograph, record the chromatogram to 2 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution (excluding the peak of the auxiliary material and the peak of the solvent before the relative retention time is 0.07), the maximum chromatographic peak adjacent to the auxiliary peak shall not be greater than 10 times (10.0%) the area of the main peak of the control solution; Other single impurity peaks shall not be greater than 0.5 times (0.5%) the area of the main peak of the control solution; the sum of the peak areas of other impurities shall not be greater than the main peak area of the control solution (1.0%).
- bacterial endotoxin take this product, check according to law (General rule 1143), each 1 mg of isoproterenol hydrochloride containing endotoxin amount should be less than 300EU.
- others should comply with the relevant provisions under injection (General 0102).
Content determination
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; With heptane sulfonate sodium solution (take heptane sulfonate sodium 1.76g, add water to dissolve)-methanol (80:20), the pH value was adjusted to 3.0 with lmol/L phosphoric acid solution as the mobile phase, and the detection wavelength was 280nm. Take an appropriate amount of adrenaline bitartrate reference, dissolve and dilute the mobile phase containing 1% sodium metabisulfite to make a solution containing 0.2mg per 1 ml as solution (1), and take an appropriate amount of isoprenaline hydrochloride reference, add 0.1% sodium metabisulfite solution to dissolve and dilute to prepare a solution containing mg per 1 ml as solution (2), take 1 ml of solution (1) and 18ml of solution (2), mix well, as the system applicable solution, take 20ul injection liquid chromatograph, the number of theoretical plate according to isoproterenol peak calculation is not less than 2000, epinephrine peak and isoproterenol peak separation degree should be greater than 3.5.
- determination of precision take this product 2ml, put 50ml flask, with 0. 1% sodium metabisulfite solution was diluted to the scale, and then shaken well. As the test solution, 20ul was accurately measured, same method determination. According to the external standard method to calculate the peak area, that is.
category
with isoprenaline hydrochloride.
specification
2ml:lmg
storage
It was sealed and kept in a cool place.
Last Update:2022-01-01 15:04:28