Epinephrine (medication)

Epinephrine, also known as adrenaline, is a medication and hormone. As a medication, it is used to treat several conditions, including anaphylaxis, cardiac arrest, asthma, and superficial bleeding. Inhaled epinephrine may be used to improve the symptoms of croup. It may also be used for asthma when other treatments are not effective. It is given intravenously, by injection into a muscle, by inhalation, or by injection just under the skin.

This article is about the medication. For this substance as a naturally occurring hormone, see Adrenaline.

Epinephrine
Skeletal formula of adrenaline
Ball-and-stick model of the zwitterionic form of adrenaline found in the crystal structure
Clinical data
Trade namesEpiPen, Adrenaclick, others
Other namesEpinephrine, adrenaline, adrenalin
AHFS/Drugs.comMonograph
MedlinePlusa603002
License data
Pregnancy
category
  • AU: A
Addiction
liability		None
Routes of
administration		Intravenous, intramuscular, endotracheal, intracardiac, nasal, eye drop
ATC code
Physiological data
ReceptorsAdrenergic receptors
MetabolismAdrenergic synapse (MAO and COMT)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Protein binding15–20%
MetabolismAdrenergic synapse (MAO and COMT)
MetabolitesMetanephrine
Onset of actionRapid
Elimination half-life2 minutes
Duration of actionFew minutes
ExcretionUrine
Identifiers
  • (R)-4-(1-Hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
Chemical and physical data
FormulaC9H13NO3
Molar mass183.207 g·mol−1
3D model (JSmol)
Density1.283±0.06 g/cm3 @ 20 °C, 760 Torr
SMILES
  • CNC[C@H](O)c1ccc(O)c(O)c1
  • InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1 Y
  • Key:UCTWMZQNUQWSLP-VIFPVBQESA-N Y

Common side effects include shakiness, anxiety, and sweating. A fast heart rate and high blood pressure may occur. Occasionally, it may result in an abnormal heart rhythm. While the safety of its use during pregnancy and breastfeeding is unclear, the benefits to the mother must be taken into account.

Epinephrine is normally produced by both the adrenal glands and a small number of neurons in the brain, where it acts as a neurotransmitter. It plays an essential role in the fight-or-flight response by increasing blood flow to muscles, heart output, pupil dilation, and blood sugar. Epinephrine does this through its effects on alpha and beta receptors. It is found in many animals and some single-celled organisms, but the medication is produced synthetically and is not harvested from animals.

Jōkichi Takamine first isolated epinephrine in 1901, and it came into medical use in 1905. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 221st most commonly prescribed medication in the United States, with more than 1 million prescriptions.

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