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P6126

Sigma-Aldrich

(R)-(−)-Phenylephrine hydrochloride

≥99% (titration), powder, α₁-adrenoceptor agonist

Synonym(s):

(R)-(−)-1-(3-Hydroxyphenyl)-2-methylaminoethanol hydrochloride, (R)-(−)-3-Hydroxy-α-(methylaminomethyl)benzyl alcohol hydrochloride

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About This Item

Linear Formula:
HOC6H4CH(CH2NHCH3)OH·HCl
CAS Number:
61-76-7
Molecular Weight:
203.67
Beilstein/REAXYS Number:
4158948
EC Number:
200-517-3
MDL number:
MFCD00012605
UNSPSC Code:
12352200
PubChem Substance ID:
57654535
NACRES:
NA.77

product name

(R)-(−)-Phenylephrine hydrochloride, powder

form

powder

Quality Level

200

mp

143-145 °C (lit.)

originator

Johnson & Johnson

SMILES string

OC1=CC([C@H](CNC)O)=CC=C1.Cl

InChI

1S/C9H13NO2.ClH/c1-10-6-9(12)7-3-2-4-8(11)5-7;/h2-5,9-12H,6H2,1H3;1H/t9-;/m0./s1

InChI key

OCYSGIYOVXAGKQ-FVGYRXGTSA-N

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146)

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General description

(R)-(-)-Phenylephrine hydrochloride is an adrenergic agent, which functions as a β-receptor sympathomimetic drug.

Application

(R)-(-)-Phenylephrine hydrochloride has been used:
  • in the preparation and culturing of cardiocytes and fibroblasts
  • to stimulate myocardial strips to measure slice contraction
  • in primary cardiomyocyte culture to show the effect of Kruppel-like factors (KLF) on cardiac hypertrophy in vivo
  • to evaluate the pharmacological response of embryonic stem cell (ESC)-derived cardiomyocytes
  • to pharmacologically rescue GATA (erythroid transcription factor) binding protein 3 (GATA3) null embryo from early embryonic lethality

Biochem/physiol Actions

α1-adrenoceptor agonist.

Features and Benefits

This compound is featured on the α1-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1B

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, 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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Clenbuterol induces cardiac myocyte hypertrophy via paracrine signalling and fibroblast-derived IGF-1
Bhavsar PK, et al.
Journal of Cardiovascular Translational Research, 3(6), 688-695 (2010)
Enantioselective synthesis of (R)-phenylephrine hydrochloride
Pandey RK, et al.
Tetrahedron Letters, 44(33), 6245-6246 (2003)
Effect of basic fibroblast growth factor on cardiomyocyte differentiation from mouse embryonic stem cells.
Khezri S, et al.
Saudi Medical Journal, 28(2), 181-186 (2007)
A myocardial slice culture model reveals alpha-1A-adrenergic receptor signaling in the human heart
Thomas RC, et al.
JACC. Basic to translational science, 1(3), 155-167 (2016)
Proper development of the outer longitudinal smooth muscle of the mouse pylorus requires Nkx2-5 and Gata3
Udager AM, et al.
Gastroenterology, 146(1), 157-165 (2014)
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Articles

α1-Adrenoceptor Characteristics and Modulators

Review alpha 1 adrenoceptors as well as their agonists, antagonists, and tissue expression patterns. We suggest several modulators and alternatives for working with a-1 adrenoreceptors.

Chromatograms

application for HPLC

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