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Merck

E4642

(±)-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
NACRES:
NA.77
PubChem Substance ID:
24278422
UNSPSC Code:
12352200
EC Number:
206-346-0
MDL number:
MFCD00050562

Product Name

(±)-Epinephrine hydrochloride,

InChI key

ATADHKWKHYVBTJ-UHFFFAOYSA-N

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

SMILES string

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

solubility

H2O: 50 mg/mL

storage temp.

2-8°C

Quality Level

200

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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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

Adrenergic receptor agonist.
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.

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.

Other Notes

The ratio of +/- adrenaline is not determined.

pictograms

Skull and crossbones
GHS06

signalword

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

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX8585
MKCX4598
MKCW8265
MKCV8354
MKCT3686

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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)
Getting the adrenaline going: crystal structure of the adrenaline-synthesizing enzyme PNMT
Martin JL, et al.
Structure, 9(10), 977-985 (2001)
Advantages and disadvantages of adrenaline in regional anaesthesia
Niemi G
Best Practice & Research. Clinical Anaesthesiology, 19(2), 229-245 (2005)
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
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)
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