Adrenaline

Epinephrine
	Skeletal formula of adrenaline
	Ball-and-stick model of the zwitterionic form of adrenaline found in the crystal structure
Clinical data
Trade names	Epipen, Adrenaclick, others
Other names	Epinephrine, adrenaline, adrenalin; 3,4,β-Trihydroxy-N-methylphenethylamine
AHFS/Drugs.com	Monograph
MedlinePlus	a603002
License data	US DailyMed: Epinephrine;
Pregnancy; category	AU: A; ;
Routes of; administration	Intravenous, intramuscular, endotracheal, intracardiac, intranasal, ophthalmic
Drug class	Adrenergic receptor agonist; Sympathomimetic
ATC code	A01AD01 (WHO) B02BC09 (WHO) C01CA24 (WHO) R01AA14 (WHO) R03AA01 (WHO) S01EA01 (WHO);
Physiological data
Receptors	Adrenergic receptors
Metabolism	Adrenergic synapse (MAO and COMT)
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	Oral: negligible; Intravenous: c. 99%; Subcutaneous: high;
Protein binding	15–20%
Metabolism	Adrenergic synapse (MAO and COMT)
Metabolites	Metanephrine
Onset of action	Rapid
Elimination half-life	2–3 minutes in plasma
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 ;
PubChem CID	5816;
IUPHAR/BPS	479;
DrugBank	DB00668 ;
ChemSpider	5611 ;
UNII	YKH834O4BH;
KEGG	D00095 ;
ChEBI	CHEBI:28918 ;
ChEMBL	ChEMBL679 ;
PDB ligand	ALE (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID5022986 ;
ECHA InfoCard	100.000.090
Chemical and physical data
Formula	C9H13NO3
Molar mass	183.207 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.283±0.06 g/cm3 @ 20 °C, 760 Torr
	SMILES CNC[C@H](O)c1ccc(O)c(O)c1;
	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 ; Key:UCTWMZQNUQWSLP-VIFPVBQESA-N ;

Adrenaline, also known as epinephrine and alternatively spelled adrenalin, 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.