4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol hydrochloride

• ChemBase ID: 73107
• Molecular Formular: C11H18ClNO3
• Molecular Mass: 247.71852
• Monoisotopic Mass: 247.09752112
• SMILES: c1c(c(cc(c1)C(O)CNC(C)C)O)O.Cl
• Canonical SMILES: CC(NCC(c1ccc(c(c1)O)O)O)C.Cl
• InChI: InChI=1S/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
• InChIKey: IROWCYIEJAOFOW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,2-diol hydrochloride
• IUPAC Traditional name: (+-)-isoproterenol hydrochloride; isoproterenol hydrochloride
• Synonyms: Isuprel; Isadrine; Euspiran; Proternol; NSC 37745; NSC 89747; Isoprenaline hydrochloride; 4-(1-hydroxy-2-(isopropylamino)ethyl)benzene-1,2-diol hydrochloride; (±)-Isoproterenol hydrochloride; 1-(3′,4′-Dihydroxyphenyl)-2-isopropylaminoethanol hydrochloride; Isoprenaline hydrochloride; Isopropylarterenol hydrochloride; Isoprenaline hydrochloride; N-Isopropyl-DL-noradrenaline hydrochloride; 1-(3',4'-Dihydroxyphenyl)-2-isopropylaminoethanol hydrochloride; DL-ISOPROTERENOL; DL-Isoprenaline hydrochloride; 4-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,2-benzenediol Hydrochloride; Isovon; Mistarel; Saventrine; Suscardia; Vapo-Iso; dl-Isadrine Hydrochloride; dl-Isoprenaline Hydrochloride; dl-Isopropylnoradrenaline Hydrochloride; dl-Isopropylnorepinephrine Hydrochloride; α-(Isopropylaminomethyl)-3,4-dihydroxybenzyl alcohol Hydrochloride; 1-(3,4-Dihydroxyphenyl)-2-(isopropylamino)ethanol Hydrochloride; Isoproterenol Hydrochloride; 4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol hydrochloride

Database IDs

• CAS Number: 51-30-9
• EC Number: 200-089-8
• MDL Number: MFCD00012603
• Beilstein Number: 3917363
• PubChem SID: 162038027; 24277780
• PubChem CID: 5807

CALCULATED PROPERTIES

• Acid pKa: 9.814519
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.1009066
• LogD (pH = 7.4): -0.9903411
• Log P: 0.24020568
• Molar Refractivity: 58.3977 cm^3
• Polarizability: 22.887892 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 164-165°C; 165-175 °C (dec.)(lit.); 166-168°C
• Density: 1.018 g/ml
• Hydrophobicity(logP): 0.153

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: DO1925000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: adrenergic receptor
• Gene Information: human ... ADRB1(153), ADRB2(154), ADRB3(155)

Product Information

• Purity: ≥98.0% (AT); 95%; 98%
• Salt Data: HCl; hydrochloride
• Empirical Formula (Hill Notation): C11H17NO3 · HCl
• Classification: Rare Derivatives of Natural Compounds

DETAILS

MP Biomedicals - 02151368

Hydrochloride
Crystalline
A Bronchodilator

MP Biomedicals - 05214068

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S2566

Biological Activity:
Isoprenaline hydrochloride is a beta-adrenergic agonist. Isoprenaline hydrochloride has a powerful stimulant action on the heart, increasing cardiac output and heart rate. Isoprenaline hydrochloride also increases blood flow to the limbs and extremities. Isoprenaline hydrochloride is a sympathomimetic medicine that dilates the small air passages in the lungs and improves the transmission of electrical signals in the heart. [1]

Sigma Aldrich - I5627

Biochem/physiol Actions
β-adrenoceptor agonist; increases cytosolic cAMP.
包装
5, 25, 100 g in poly bottle

Sigma Aldrich - I27902

Biochem/physiol Actions
β-adrenoceptor agonist; increases cytosolic cAMP.
Packaging
25 g in poly bottle

Sigma Aldrich - 59650

Biochem/physiol Actions
β-adrenoceptor agonist; increases cytosolic cAMP.

Toronto Research Chemicals - I874200

Isoproterenol is a non-selective beta-adrenergic agonist. Isoproterenol is used in the treatment of bradycardia; bronchodilator.

REFERENCES

• http://en.wikipedia.org/wiki/Isoprenaline
• Kikkawa, H. et al.: Biol. Pharmac. Bull., 17, 1047 (1994)
• Kral, P. et al.: Psychopharmacologia, 26, 79 (1994)
• Giles, R.E. et al.: J. Pharmacol. Exp. Ther., 186, 472 (1994)