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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:
329-63-5
Molecular Weight:
219.67
EC Number:
206-346-0
MDL number:
MFCD00050562
UNSPSC Code:
12352200
PubChem Substance ID:
24278422
NACRES:
NA.77

product name

(±)-Epinephrine hydrochloride,

Quality Level

200

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

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152) , ADRB1(153) , ADRB2(154) , ADRB3(155)

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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
GHS06

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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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Effects of an epinephrine infusion on eye temperature and heart rate variability in bull calves
Stewart M, et al.
Journal of Dairy Science, 93(11), 5252-5257 (2010)
Adrenaline, cardiac arrest, and evidence based medicine.
Rainer TH and Robertson CE
Emergency Medicine Journal : EMJ, 13(4), 234-237 (1996)
Hao Lu et al.
Biology open, 9(5) (2020-05-16)
Reissner fibre (RF), discovered by the 19th-century German anatomist Ernst Reissner, is a filamentous structure present in cerebrospinal fluid (CSF). RF forms by aggregation of a glycoprotein called SCO-spondin (Sspo), but its function has remained enigmatic. Recent studies have shown
Advantages and disadvantages of adrenaline in regional anaesthesia
Niemi G
Best Practice & Research. Clinical Anaesthesiology, 19(2), 229-245 (2005)
Sympathetic predominance is associated with impaired endothelial progenitor cells and tunneling nanotubes in controlled-hypertensive patients
de Cavanagh EAMV, et al.
American Journal of Physiology. Heart and Circulatory Physiology, 307, H207?H215-H207?H215 (2014)
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