Adrenaline

Epinephrine

Clinical data
Trade names	EpiPen, Adrenaclick, others
AHFS/Drugs.com	Monograph
MedlinePlus	a603002
License data	US FDA: epinephrine
Pregnancy category	US: C (Risk not ruled out)
Addiction liability	None
Routes of administration	IV, IM, endotracheal, IC, nasal, eye drop
ATC code	A01AD01 (WHO) B02BC09 (WHO) C01CA24 (WHO) R01AA14 (WHO) R03AA01 (WHO) S01EA01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: Prescription only/OTC
Pharmacokinetic data
Metabolism	adrenergic synapse (MAO and COMT)
Onset of action	Rapid
Biological half-life	2 minutes
Duration of action	Few minutes
Excretion	Urine
Identifiers
IUPAC name (R)-4-(1-Hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
CAS Number	51-43-4 Y
PubChem (CID)	5816
IUPHAR/BPS	479
DrugBank	DB00668 Y
ChemSpider	5611 Y
UNII	YKH834O4BH Y
KEGG	D00095 Y
ChEBI	CHEBI:28918 Y
ChEMBL	CHEMBL679 Y
PDB ligand ID	ALE (PDBe, RCSB PDB)
ECHA InfoCard	100.000.090
Chemical and physical data
Formula	C9H13NO3
Molar mass	183.204 g/mol
3D model (Jmol)	Interactive image
Density	1.283±0.06 g/cm3 @ 20 °C, 760 Torr
SMILES Oc1ccc(cc1O)[C@@H](O)CNC
InChI 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

Epinephrine, also known as adrenalin or adrenaline, is a hormone, neurotransmitter and medication. Epinephrine is normally produced by both the adrenal glands and certain neurons. It plays an important role in the fight-or-flight response by increasing blood flow to muscles, output of the heart, pupil dilation, and blood sugar. Epinephrine does this by its effects on alpha and beta receptors. It is found in many animals and some one cell organisms.Jokichi Takamine first isolated epinephrine in 1901.

As a medication it is used to treat a number of conditions, including anaphylaxis, cardiac arrest, 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. 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.

The adrenal medulla is a minor contributor to total circulating catecholamines (L-DOPA is at a higher concentration in the plasma), though it contributes over 90% of circulating epinephrine. Little epinephrine is found in other tissues, mostly in scattered chromaffin cells. Following adrenalectomy, epinephrine disappears below the detection limit in the blood stream.