Adrenaline

Adrenaline, also known as epinephrine, is a hormone and medication which is involved in regulating visceral functions (e.g., respiration). It appears as a white microcrystalline granule. Adrenaline is normally produced by the adrenal glands and by a small number of neurons in the medulla oblongata. It plays an essential role in the fight-or-flight response by increasing blood flow to muscles, heart output by acting on the SA node, pupil dilation response, and blood sugar level. It does this by binding to alpha and beta receptors. It is found in many animals, including humans, and some single-celled organisms. It has also been isolated from the plant Scoparia dulcis found in Northern Vietnam.

This article is about the natural hormone. For this substance when used as a medication, see Epinephrine (medication). For other uses, see Adrenaline (disambiguation).

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
CompTox Dashboard (EPA)
ECHA InfoCard100.000.090
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
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