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I6504

Sigma-Aldrich

(−)-Isoproterenol hydrochloride

≥98% (TLC), powder, β-adrenoceptor agonist

Synonym(s):

(−)-Isoprenaline hydrochloride, (−)-N-Isopropyl-L-noradrenaline hydrochloride, (R)-3,4-Dihydroxy-α-(isopropylaminomethyl)benzyl alcohol hydrochloride

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About This Item

Linear Formula:
3,4-(HO)2C6H3CH(OH)CH2NHCH(CH3)2·HCl
CAS Number:
5984-95-2
Molecular Weight:
247.72
Beilstein/REAXYS Number:
6077193
MDL number:
MFCD00064548
UNSPSC Code:
12352200
PubChem Substance ID:
24278495
NACRES:
NA.77

product name

(−)-Isoproterenol hydrochloride,

mp

175 °C (dec.) (lit.)

solubility

soluble (50 mg/ml: H2O)

storage temp.

−20°C

SMILES string

Cl[H].CC(C)NC[C@H](O)c1ccc(O)c(O)c1

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/t11-;/m0./s1

InChI key

IROWCYIEJAOFOW-MERQFXBCSA-N

Gene Information

human ... ADRB2(154)

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Application

(−)-Isoproterenol hydrochloride has been used in in vitro explant culture. It has also been used in transcriptome analysis of heart.

Biochem/physiol Actions

Isoproterenol hydrochloride is useful in post transplantal organ recovery. It exhibits ionotropic and chronotropic effects. With respect to donor heart recovery, isoproterenol hydrochloride decreases peripheral and systemic vascular resistance. Isoproterenol also increases the heart rate.
β-adrenoceptor agonist; increases cytosolic cAMP.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Anne-Marie Schönegge et al.
Nature communications, 8(1), 2169-2169 (2017-12-20)
Functional selectivity of G-protein-coupled receptors is believed to originate from ligand-specific conformations that activate only subsets of signaling effectors. In this study, to identify molecular motifs playing important roles in transducing ligand binding into distinct signaling responses, we combined in
Acute Care Handbook for Physical Therapists, 414-414 (2008)
Michael H Lai et al.
American journal of physiology. Heart and circulatory physiology, 307(9), H1327-H1338 (2014-08-31)
Large-conductance Ca(2+)- and voltage-activated K(+) (BK) channels play prominent roles in shaping muscle and neuronal excitability. In the cardiovascular system, BK channels promote vascular relaxation and protect against ischemic injury. Recently, inhibition of BK channels has been shown to lower
Seon Jin Lee et al.
Stem cells international, 2018, 7453161-7453161 (2018-12-05)
Cross talks between the renin-angiotensin system (RAS), sympathetic nervous system, and vascular homeostasis are tightly coordinated in hypertension. Angiotensin II (Ang II), a key factor in RAS, when abnormally activated, affects the number and bioactivity of circulating human endothelial progenitor
Influence of adipocyte size and adipose depot on the in vitro lipolytic activity and insulin sensitivity of adipose tissue in dairy cows at the end of the dry period
De Koster J, et al.
Journal of Dairy Science, 99(3), 2319-2328 (2016)
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