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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:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Kui Zhai et al.
PloS one, 7(10), e47826-e47826 (2012-10-25)
We investigated the role of cyclic nucleotide phosphodiesterases (PDEs) in the spatiotemporal control of intracellular cAMP concentrations in rat aortic smooth muscle cells (RASMCs). The rank order of PDE families contributing to global cAMP-PDE activity was PDE4> PDE3  =  PDE1.
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
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De Koster J, et al.
Journal of Dairy Science, 99(3), 2319-2328 (2016)
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