1.0 2011-09-21 00:04:37 UTC 2025-11-19 02:40:18 UTC FDB021889 Epinephrine Epinephrine is a catecholamine, a sympathomimetic monoamine derived from the amino acids phenylalanine and tyrosine. It is the active sympathomimetic hormone secreted from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics. Epinephrine also constricts arterioles in the skin and gut while dilating arterioles in leg muscles. It elevates the blood sugar level by increasing hydrolysis of glycogen to glucose in the liver, and at the same time begins the breakdown of lipids in adipocytes. Epinephrine has a suppressive effect on the immune system. [HMDB] (-)-(R)-Epinephrine (-)-3,4-Dihydroxy-a-((methylamino)methyl)benzyl alcohol (-)-3,4-dihydroxy-a-[(methylamino)methyl]-Benzyl alcohol (-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol (-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol (-)-3,4-dihydroxy-alpha-[(methylamino)methyl]-Benzyl alcohol (-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol (-)-3,4-Dihydroxy-α-((methylamino)methyl)benzyl alcohol (-)-Adrenaline (-)-Epinephrine (R)-(-)-Adnephrine (R)-(-)-Adrenaline (R)-(-)-Epinephrine (R)-(-)-Epirenamine (R)-4-[1-hydroxy-2-(methylamino)ethyl]-1,2-Benzenediol (R)-Adrenaline (R)-Epinephrine 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-1,2-Benzenediol Adnephrine Adrenal Adrenalin Adrenaline Adrenine Adrin Ana-Kit Bosmin Bronkaid Mist Chelafrin Epifrin Epiglaufrin Epinefrina Epinephran Epinephrin Epinephrine Epinephrinum Epipen Epipen jr Epirenan Eppy Exadrin Glauposine Hemisine Hemostasin Hemostatin Hypernephrin Isoptoepinal l-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol L-Adrenaline l-Epinephrine l-Epirenamine L-Methylaminoethanolcatechol Levoepinephrine Levorenen Levorenin Levorenine Levoreninum Lyodrin Methylarterenol Mucidrina Nephridine Nieraline Paranephrin Primatene Primatene Mist R-(-)-Epinephrine Renaglandin Renaleptine Renalina Renoform Renostypticin Renostyptin Scurenaline Simplene Styptirenal Supracapsulin Supranephrane Suprarenaline Suprarenin Surrenine Sus-phrine Takamina Vasoconstrictine Vasotonin C9H13NO3 183.2044 183.089543287 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol epinephrine 51-43-4 CNC[C@H](O)C1=CC(O)=C(O)C=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 UCTWMZQNUQWSLP-VIFPVBQESA-N belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Catechols Organic compounds Benzenoids Phenols Benzenediols Aromatic homomonocyclic compounds 1,2-aminoalcohols 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Aralkylamines Aromatic alcohols Benzene and substituted derivatives Dialkylamines Hydrocarbon derivatives Organopnictogen compounds Secondary alcohols 1,2-aminoalcohol 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid Alcohol Amine Aralkylamine Aromatic alcohol Aromatic homomonocyclic compound Catechol Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary alcohol Secondary aliphatic amine Secondary amine Adrenalines Biogenic amines adrenaline Solid logp -0.82 ALOGPS logs -0.99 ALOGPS solubility 1.86e+01 g/l ALOGPS logp -0.43 ChemAxon pka_strongest_acidic 9.69 ChemAxon pka_strongest_basic 8.91 ChemAxon iupac 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol ChemAxon average_mass 183.2044 ChemAxon mono_mass 183.089543287 ChemAxon smiles CNC[C@H](O)C1=CC(O)=C(O)C=C1 ChemAxon formula C9H13NO3 ChemAxon 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 ChemAxon inchikey UCTWMZQNUQWSLP-VIFPVBQESA-N ChemAxon polar_surface_area 72.72 ChemAxon refractivity 49.23 ChemAxon polarizability 19.04 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Catecholamine Biosynthesis SMP00012 map00350 Tyrosine Metabolism SMP00006 map00350 HMDB00068 28918 #<Reference:0x0000558b626c3098> #<Reference:0x0000558b626c2eb8> #<Reference:0x0000558b626c2cd8> #<Reference:0x0000558b626c2b20> #<Reference:0x0000558b626c2940> #<Reference:0x0000558b626c2760> #<Reference:0x0000558b626c2580> #<Reference:0x0000558b626c23a0> #<Reference:0x0000558b626c21c0> #<Reference:0x0000558b626c1fe0> #<Reference:0x0000558b626c1e00> #<Reference:0x0000558b626c1c20> #<Reference:0x0000558b626c1a40> #<Reference:0x0000558b626c1888> #<Reference:0x0000558b626c16a8> #<Reference:0x0000558b626c14c8> #<Reference:0x0000558b626c12c0> #<Reference:0x0000558b626c10b8> #<Reference:0x0000558b626c0e60> #<Reference:0x0000558b626c0c58> Anatidae Type 1 specific Anatidae 8830 Avocado Type 1 specific Persea americana 3435 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columba 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 Animal Capra aegagrus hircus 9925 Domestic pig Type 1 Animal Sus scrofa domesticus 9825 Eggplant Type 1 specific Solanum melongena 4111 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus cuniculus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus hemionus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Alpha-2A adrenergic receptor P08913 ADRA2A Alpha-2B adrenergic receptor P18089 ADRA2B Beta-1 adrenergic receptor P08588 ADRB1 Beta-2 adrenergic receptor P07550 ADRB2 Phenylalanine-4-hydroxylase P00439 PAH