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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:51 UTC
HMDB IDHMDB00068
Secondary Accession Numbers
  • HMDB00615
Metabolite Identification
Common NameEpinephrine
DescriptionEpinephrine 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.
Structure
Thumb
Synonyms
  1. (-)-(R)-Epinephrine
  2. (-)-3,4-dihydroxy-a-[(methylamino)methyl]-Benzyl alcohol
  3. (-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol
  4. (-)-3,4-dihydroxy-alpha-[(methylamino)methyl]-Benzyl alcohol
  5. (-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol
  6. (-)-Adrenaline
  7. (-)-Epinephrine
  8. (R)-4-[1-hydroxy-2-(methylamino)ethyl]-1,2-Benzenediol
  9. (R)-Adrenaline
  10. (R)-Epinephrine
  11. 4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-Benzenediol
  12. Adnephrine
  13. Adrenal
  14. Adrenalin
  15. Adrenaline
  16. Adrenine
  17. Adrin
  18. Ana-Kit
  19. Bosmin
  20. Bronkaid Mist
  21. Chelafrin
  22. Epifrin
  23. Epiglaufrin
  24. Epinefrina
  25. Epinephran
  26. Epinephrine
  27. Epipen
  28. Epirenan
  29. Eppy
  30. Exadrin
  31. Glauposine
  32. Hemisine
  33. Hemostasin
  34. Hemostatin
  35. Hypernephrin
  36. Isoptoepinal
  37. L-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
  38. L-Adrenaline
  39. L-Epinephrine
  40. L-Epirenamine
  41. L-Methylaminoethanolcatechol
  42. Levoepinephrine
  43. Levorenen
  44. Levorenin
  45. Levorenine
  46. Levoreninum
  47. Lyodrin
  48. Methylarterenol
  49. Mucidrina
  50. Nephridine
  51. Nieraline
  52. Paranephrin
  53. Primatene Mist
  54. R-(-)-Epinephrine
  55. Renaglandin
  56. Renaleptine
  57. Renalina
  58. Renoform
  59. Renostypticin
  60. Renostyptin
  61. Scurenaline
  62. Simplene
  63. Styptirenal
  64. Supracapsulin
  65. Supranephrane
  66. Suprarenaline
  67. Suprarenin
  68. Surrenine
  69. Sus-phrine
  70. Takamina
  71. Vasoconstrictine
  72. Vasotonin
Chemical FormulaC9H13NO3
Average Molecular Weight183.2044
Monoisotopic Molecular Weight183.089543287
IUPAC Name4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
Traditional Nameepinephrine
CAS Registry Number51-43-4
SMILES
CNC[C@H](O)C1=CC=C(O)C(O)=C1
InChI Identifier
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
InChI KeyUCTWMZQNUQWSLP-VIFPVBQESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassPhenols and Derivatives
Sub ClassBenzenediols
Other Descriptors
  • Adrenalines(KEGG)
  • Aromatic Homomonocyclic Compounds
  • Biogenic amines(KEGG)
  • adrenaline(ChEBI)
Substituents
  • 1,2 Aminoalcohol
  • 1,2 Diphenol
  • Benzyl Alcohol Derivative
  • Phenethylamine
  • Secondary Alcohol
  • Secondary Aliphatic Amine (Dialkylamine)
Direct ParentCatecholamines and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point211.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.18 mg/mLNot Available
LogP-1.37HANSCH,C & LEO,AJ (1985)
Predicted Properties
PropertyValueSource
Water Solubility18.6ALOGPS
logP-0.82ALOGPS
logP-0.43ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)9.69ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.23 m3·mol-1ChemAxon
Polarizability19.18 Å3ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Gonads
  • Gut
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Myelin
  • Nerve Cells
  • Nervous Tissues
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012map00350
Tyrosine MetabolismSMP00006map00350
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00164 +/- 0.00012 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00029 +/- 0.000021 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.00072 (0.00049-0.0013) uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified0.0003 +/- 0.00003 uMAdult (>18 years old)MaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0(0.0-0.00022) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000235 +/- 3.277e-05 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.034 (0.0063-0.062) uMAdult (>18 years old)FemaleNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00024 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified0.0057 +/- 0.00092 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.002 +/- 0.00099 umol/mmol creatinineChildren (1-13 years old)BothNormal details
UrineDetected and Quantified0.0052 (0.00043-0.0099) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0021 (0.00098-0.0052) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00241 +/- 0.00057 uMAdult (>18 years old)BothHead trauma details
BloodDetected and Quantified0.000077 +/- 0.000025 uMAdult (>18 years old)FemaleAddison's disease details
BloodDetected and Quantified0.001 +/- 0.00036 uMAdult (>18 years old)BothSubarachnoid haemorrhage details
BloodDetected and Quantified0.00014 +/- 0.000036 uMAdult (>18 years old)MaleAddison's disease details
BloodDetected and Quantified0.00029 (0.00005-0.00054) uMAdult (>18 years old)Both
Pheochromocytoma
details
BloodDetected and Quantified0.0025 (0.0002-0.0048) uMAdult (>18 years old)Both
Pheochromocytoma
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000453 +/- 4.916e-05 uMAdult (>18 years old)Not Specifiedborderline hypertensives details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000147 +/- 0.000109 uMAdult (>18 years old)Not SpecifiedCerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000109 uMAdult (>18 years old)Not SpecifiedCerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value but renal insufficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000251 uMAdult (>18 years old)Not SpecifiedHaemorrhagic infraction details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000300 uMAdult (>18 years old)Not SpecifiedBacterial meningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000481 uMAdult (>18 years old)Not SpecifiedLeucemic meningiosa details
Cerebrospinal Fluid (CSF)Detected and Quantified0.000153 uMAdult (>18 years old)Not SpecifiedEncephalitis details
UrineDetected and Quantified0.011 +/- 0.0022 umol/mmol creatinineAdult (>18 years old)BothExercise details
Associated Disorders and Diseases
Disease References
Addison's Disease
  1. Bornstein SR, Breidert M, Ehrhart-Bornstein M, Kloos B, Scherbaum WA: Plasma catecholamines in patients with Addison's disease. Clin Endocrinol (Oxf). 1995 Feb;42(2):215-8. Pubmed: 7704967
Subarachnoid hemorrhage
  1. Lambert G, Naredi S, Eden E, Rydenhag B, Friberg P: Monoamine metabolism and sympathetic nervous activation following subarachnoid haemorrhage: influence of gender and hydrocephalus. Brain Res Bull. 2002 May;58(1):77-82. Pubmed: 12121816
Head injury
  1. Lambert G, Naredi S, Eden E, Rydenhag B, Friberg P: Monoamine metabolism and sympathetic nervous activation following subarachnoid haemorrhage: influence of gender and hydrocephalus. Brain Res Bull. 2002 May;58(1):77-82. Pubmed: 12121816
Pheochromocytoma
  1. Eisenhofer G, Keiser H, Friberg P, Mezey E, Huynh TT, Hiremagalur B, Ellingson T, Duddempudi S, Eijsbouts A, Lenders JW: Plasma metanephrines are markers of pheochromocytoma produced by catechol-O-methyltransferase within tumors. J Clin Endocrinol Metab. 1998 Jun;83(6):2175-85. Pubmed: 9626157
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021889
KNApSAcK IDNot Available
Chemspider ID5611
KEGG Compound IDC00788
BioCyc IDL-EPINEPHRINE
BiGG ID35997
Wikipedia LinkEpinephrine
NuGOwiki LinkHMDB00068
Metagene LinkHMDB00068
METLIN ID5127
PubChem Compound5816
PDB IDNot Available
ChEBI ID28918
References
Synthesis ReferenceSinger, Robert A.; Carreira, Erick M. An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine. Tetrahedron Letters (1997), 38(6), 927-930.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Blagitko N, Schulz U, Schinzel AA, Ropers HH, Kalscheuer VM: gamma2-COP, a novel imprinted gene on chromosome 7q32, defines a new imprinting cluster in the human genome. Hum Mol Genet. 1999 Dec;8(13):2387-96. Pubmed: 10556286
  2. Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. Pubmed: 12649306
  3. Kurtis JD, Friedman JF, Leenstra T, Langdon GC, Wu HW, Manalo DL, Su L, Jiz M, Jarilla B, Pablo AO, McGarvey ST, Olveda RM, Acosta LP: Pubertal development predicts resistance to infection and reinfection with Schistosoma japonicum. Clin Infect Dis. 2006 Jun 15;42(12):1692-8. Epub 2006 May 12. Pubmed: 16705573
  4. Eisenhofer G, Keiser H, Friberg P, Mezey E, Huynh TT, Hiremagalur B, Ellingson T, Duddempudi S, Eijsbouts A, Lenders JW: Plasma metanephrines are markers of pheochromocytoma produced by catechol-O-methyltransferase within tumors. J Clin Endocrinol Metab. 1998 Jun;83(6):2175-85. Pubmed: 9626157
  5. Igdoura SA, Gafuik C, Mertineit C, Saberi F, Pshezhetsky AV, Potier M, Trasler JM, Gravel RA: Cloning of the cDNA and gene encoding mouse lysosomal sialidase and correction of sialidase deficiency in human sialidosis and mouse SM/J fibroblasts. Hum Mol Genet. 1998 Jan;7(1):115-21. Pubmed: 9384611
  6. Kaufer D, Ogle WO, Pincus ZS, Clark KL, Nicholas AC, Dinkel KM, Dumas TC, Ferguson D, Lee AL, Winters MA, Sapolsky RM: Restructuring the neuronal stress response with anti-glucocorticoid gene delivery. Nat Neurosci. 2004 Sep;7(9):947-53. Epub 2004 Aug 8. Pubmed: 15300253
  7. Yasuda G, Umemura S, Ishii M: Characterization of bunazosin-sensitive alpha1-adrenoceptors in human renal medulla. J Cardiovasc Pharmacol. 1997 Aug;30(2):163-8. Pubmed: 9269942
  8. Gear AR, Camerini D: Platelet chemokines and chemokine receptors: linking hemostasis, inflammation, and host defense. Microcirculation. 2003 Jun;10(3-4):335-50. Pubmed: 12851650
  9. Wilson BS, Petrella E, Lowe SR, Lien K, Mackensen DG, Gridley DS, Stickney DR: Radiolocalization of human small cell lung cancer and antigen-positive normal tissues using monoclonal antibody LS2D617. Cancer Res. 1990 May 15;50(10):3124-30. Pubmed: 2159374
  10. Blakely RD, Apparsundaram S: Structural diversity in the catecholamine transporter gene family: molecular cloning and characterization of an L-epinephrine transporter from bullfrog sympathetic ganglia. Adv Pharmacol. 1998;42:206-10. Pubmed: 9327880
  11. Belloni AS, Albertin G, Forneris ML, Nussdorfer GG: Proadrenomedullin-derived peptides as autocrine-paracrine regulators of cell growth. Histol Histopathol. 2001 Oct;16(4):1263-74. Pubmed: 11642745
  12. Contreras LN, Arregger AL, Persi GG, Gonzalez NS, Cardoso EM: A new less-invasive and more informative low-dose ACTH test: salivary steroids in response to intramuscular corticotrophin. Clin Endocrinol (Oxf). 2004 Dec;61(6):675-82. Pubmed: 15579180
  13. Kushnir MM, Rockwood AL, Roberts WL, Pattison EG, Owen WE, Bunker AM, Meikle AW: Development and performance evaluation of a tandem mass spectrometry assay for 4 adrenal steroids. Clin Chem. 2006 Aug;52(8):1559-67. Epub 2006 Jun 15. Pubmed: 16777916
  14. Krohn K, Uibo R, Aavik E, Peterson P, Savilahti K: Identification by molecular cloning of an autoantigen associated with Addison's disease as steroid 17 alpha-hydroxylase. Lancet. 1992 Mar 28;339(8796):770-3. Pubmed: 1347802
  15. Bornstein SR, Breidert M, Ehrhart-Bornstein M, Kloos B, Scherbaum WA: Plasma catecholamines in patients with Addison's disease. Clin Endocrinol (Oxf). 1995 Feb;42(2):215-8. Pubmed: 7704967
  16. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
  17. Hiroi N, Yanagisawa R, Yoshida-Hiroi M, Endo T, Kawase T, Tsuchida Y, Toyama K, Shibuya K, Nakata K, Yoshino G: Retroperitoneal hemorrhage due to bilateral adrenal metastases from lung adenocarcinoma. J Endocrinol Invest. 2006 Jun;29(6):551-4. Pubmed: 16840834
  18. Kennedy B, Bigby TD, Ziegler MG: Nonadrenal epinephrine-forming enzymes in humans. Characteristics, distribution, regulation, and relationship to epinephrine levels. J Clin Invest. 1995 Jun;95(6):2896-902. Pubmed: 7769131
  19. Panholzer TJ, Beyer J, Lichtwald K: Coupled-column liquid chromatographic analysis of catecholamines, serotonin, and metabolites in human urine. Clin Chem. 1999 Feb;45(2):262-8. Pubmed: 9931050
  20. De Bellis MD, Baum AS, Birmaher B, Keshavan MS, Eccard CH, Boring AM, Jenkins FJ, Ryan ND: A.E. Bennett Research Award. Developmental traumatology. Part I: Biological stress systems. Biol Psychiatry. 1999 May 15;45(10):1259-70. Pubmed: 10349032

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
Reactions
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
Reactions
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
S-Adenosylmethionine + Epinephrine → S-Adenosylhomocysteine + Metanephrinedetails
General function:
Involved in amino acid binding
Specific function:
Not Available
Gene Name:
PAH
Uniprot ID:
P00439
Molecular weight:
51861.565
General function:
Involved in methyltransferase activity
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P11086
Molecular weight:
30854.745
Reactions
S-Adenosylmethionine + Norepinephrine → S-Adenosylhomocysteine + Epinephrinedetails
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:
ADRB1
Uniprot ID:
P08588
Molecular weight:
51322.1
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:
ADRB2
Uniprot ID:
P07550
Molecular weight:
46458.3
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for trace amines, including beta- phenylethylamine (b-PEA), p-tyramine (p-TYR), octopamine and tryptamine, with highest affinity for b-PEA and p-TYR. Unresponsive to classical biogenic amines, such as epinephrine and histamine and only partially activated by dopamine and serotonine. Trace amines are biogenic amines present in very low levels in mammalian tissues. Although some trace amines have clearly defined roles as neurotransmitters in invertebrates, the extent to which they function as true neurotransmitters in vertebrates has remained speculative. Trace amines are likely to be involved in a variety of physiological functions that have yet to be fully understood. The signal transduced by this receptor is mediated by the G(s)-class of G-proteins which activate adenylate cyclase
Gene Name:
TAAR1
Uniprot ID:
Q96RJ0
Molecular weight:
39091.3