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E4642

Sigma-Aldrich

(±)-Epinephrine hydrochloride

≥98% (TLC), powder, adrenergic receptor agonist

Synonym(s):

(±)-Adrenalin, 4-(1-Hydroxy-2-[methylamino]ethyl)-1,2-benzenediol hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C9H13NO3 · HCl
CAS Number:
Molecular Weight:
219.67
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

product name

(±)-Epinephrine hydrochloride,

Quality Level

solubility

H2O: 50 mg/mL

storage temp.

2-8°C

SMILES string

OC(CNC)C1=CC=C(O)C(O)=C1.Cl

InChI

1S/C9H13NO3.ClH/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;/h2-4,9-13H,5H2,1H3;1H

InChI key

ATADHKWKHYVBTJ-UHFFFAOYSA-N

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General description

Epinephrine (adrenalin) is synthesized from norepinephrine (noradrenalin) by the action of the enzyme phenylethanolamine N-methyltransferase. Epinephrine comprises 5%-10% of the total catecholamines in the central nervous system. It is a mixed α/β-adrenergic receptor agonist and stimulates these receptors. Their site of synthesis is adrenal medulla and it travels through the vascular systems. Its breakdown occurs in the central nervous system (CNS), liver and kidney.

Application

(±)-Epinephrine hydrochloride has been used:
  • in the induction of renalase expression in Human renal proximal tubular epithelial cells
  • in the infusion studies to test its effect on heart rate and eye temperature measurements in bull
  • as a medium supplement for the stimulation of endothelial progenitor cells

Biochem/physiol Actions

Epinephrine improves systemic pressure during cardiopulmonary resuscitation and is used post cardiac arrest. The levels of epinephrine increases during trauma, sepsis and hypoglycemia resulting in increased cardiac rate and contractility. It is used in the treatment of acute anaphylaxis. Use of epinephrine hydrochloride enables dilation of pupil during intraocular lens (IOL) implantation surgery.
Adrenergic receptor agonist.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

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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Getting the adrenaline going: crystal structure of the adrenaline-synthesizing enzyme PNMT
Martin JL, et al.
Structure, 9(10), 977-985 (2001)
M Stewart et al.
Journal of dairy science, 93(11), 5252-5257 (2010-10-23)
Changes in autonomic nervous system (ANS) activity are one of the first phases of a stress response, but they are rarely used to assess the welfare of farm animals. Eye temperature measured using infrared thermography (IRT) is proposed as an
Pupil dilation with intracameral epinephrine hydrochloride during phacoemulsification and intraocular lens implantation
Yu A, et al.
Journal of Ophthalmology, 2016 (2016)
Mhairi A Sutherland et al.
PloS one, 15(5), e0233558-e0233558 (2020-05-30)
Eye temperature measured using infrared thermography (IRT) can be used as a non-invasive measure of autonomic nervous system (ANS) activity in cattle. The objective of this study was to evaluate if changes in eye temperature (measured using IRT) can be
Epinephrine: the drug of choice for anaphylaxis-a statement of the World Allergy Organization
Kemp SF, et al.
The World Allergy Organization journal, 1(2), S18-S18 (2008)

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