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P6126

Sigma-Aldrich

(R)-(−)-Phenylephrine hydrochloride

powder

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Synonym(s):
(R)-(−)-1-(3-Hydroxyphenyl)-2-methylaminoethanol hydrochloride, (R)-(−)-3-Hydroxy-α-(methylaminomethyl)benzyl alcohol hydrochloride
Linear Formula:
HOC6H4CH(CH2NHCH3)OH·HCl
CAS Number:
61-76-7
Molecular Weight:
203.67
Beilstein:
4158948
EC Number:
200-517-3
MDL number:
MFCD00012605
UNSPSC Code:
12352200
PubChem Substance ID:
57654535
NACRES:
NA.77

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

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1B

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

新产品

Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

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    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. Is (R)-(-)-Phenylephrine hydrochloride the same as L-Phenylephrine hydrochloride?

    (R)-(-)-Phenylephrine hydrochloride is also named l-Phenylephrine hydrochloride (lower case el) or Levophenylephrine hydrochloride.

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    Ask a Scientist here.

Kruppel-like factor 4 regulates pressure-induced cardiac hypertrophy
Liao X, et al.
Journal of Molecular and Cellular Cardiology, 49(2), 334-338 (2010)
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)
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)
View All Related Papers

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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