Human Metabolome Database Version 3.5

Showing metabocard for Epinephrine (HMDB00068)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:51 -0700
HMDB ID HMDB00068
Secondary Accession Numbers
  • HMDB00615
Metabolite Identification
Common Name Epinephrine
Description 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.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H13NO3
Average Molecular Weight 183.2044
Monoisotopic Molecular Weight 183.089543287
IUPAC Name 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
Traditional IUPAC Name epinephrine
CAS Registry Number 51-43-4
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 Key UCTWMZQNUQWSLP-VIFPVBQESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Benzenediols
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 Parent Catecholamines and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 211.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.18 mg/mL Not Available
LogP -1.37 HANSCH,C & LEO,AJ (1985)
Predicted Properties
Property Value Source
Water Solubility 18.6 g/L ALOGPS
LogP -0.82 ALOGPS
LogP -0.43 ChemAxon
LogS -0.99 ALOGPS
pKa (strongest acidic) 9.69 ChemAxon
pKa (strongest basic) 8.91 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 72.72 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 49.23 ChemAxon
Polarizability 19.18 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Kidney
  • Liver
  • Epidermis
  • Myelin
  • Adrenal Gland
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Medulla
  • Nerve Cells
  • Platelet
  • Gonads
  • Gut
  • Eye Lens
  • Nervous Tissues
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
Catecholamine Biosynthesis SMP00012 map00350 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.00164 +/- 0.00012 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.00029 +/- 0.000021 uM Adult (>18 years old) Female Normal
Blood Detected and Quantified
0.00072 (0.00049-0.0013) uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
0.0003 +/- 0.00003 uM Adult (>18 years old) Male Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0(0.0-0.00022) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.000235 +/- 3.277e-05 uM Not Specified Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.034 (0.0063-0.062) uM Adult (>18 years old) Female Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.00024 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
0.0057 +/- 0.00092 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.002 +/- 0.00099 umol/mmol creatinine Children (1-13 year old) Both Normal
Urine Detected and Quantified
0.0052 (0.00043-0.0099) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.0021 (0.00098-0.0052) umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.00241 +/- 0.00057 uM Adult (>18 years old) Both Head trauma
Blood Detected and Quantified 0.000077 +/- 0.000025 uM Adult (>18 years old) Female Addison's disease
Blood Detected and Quantified 0.001 +/- 0.00036 uM Adult (>18 years old) Both Subarachnoid haemorrhage
Blood Detected and Quantified 0.00014 +/- 0.000036 uM Adult (>18 years old) Male Addison's disease
Blood Detected and Quantified 0.00029 (0.00005-0.00054) uM Adult (>18 years old) Both Comment Pheochromocytoma
Blood Detected and Quantified 0.0025 (0.0002-0.0048) uM Adult (>18 years old) Both Comment Pheochromocytoma
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000453 +/- 4.916e-05 uM Adult (>18 years old) Not Specified borderline hypertensives
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000147 +/- 0.000109 uM Adult (>18 years old) Not Specified Cerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000109 uM Adult (>18 years old) Not Specified Cerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value but renal insufficiency
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000251 uM Adult (>18 years old) Not Specified Haemorrhagic infraction
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000300 uM Adult (>18 years old) Not Specified Bacterial meningitis
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000481 uM Adult (>18 years old) Not Specified Leucemic meningiosa
Cerebrospinal Fluid (CSF) Detected and Quantified 0.000153 uM Adult (>18 years old) Not Specified Encephalitis
Urine Detected and Quantified 0.011 +/- 0.0022 umol/mmol creatinine Adult (>18 years old) Both Exercise
Associated Disorders and Diseases
Disease References
Addison's Disease
  • 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 Link_out
      Subarachnoid hemorrhage
      • 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 Link_out
          Pheochromocytoma
          • 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 Link_out
              Head injury
              • 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 Link_out
                  Associated OMIM IDs
                  DrugBank ID Not Available
                  DrugBank Metabolite ID Not Available
                  Phenol Explorer Compound ID Not Available
                  Phenol Explorer Metabolite ID Not Available
                  FoodDB ID FDB021889
                  KNApSAcK ID Not Available
                  Chemspider ID 5611 Link_out
                  KEGG Compound ID C00788 Link_out
                  BioCyc ID L-EPINEPHRINE Link_out
                  BiGG ID 35997 Link_out
                  Wikipedia Link Epinephrine Link_out
                  NuGOwiki Link HMDB00068 Link_out
                  Metagene Link HMDB00068 Link_out
                  METLIN ID 5127 Link_out
                  PubChem Compound 5816 Link_out
                  PDB ID Not Available
                  ChEBI ID 28918 Link_out
                  References
                  Synthesis Reference Singer, 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. 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 Link_out
                  2. 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 Link_out
                  3. 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 Link_out
                  4. 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 Link_out
                  5. 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 Link_out
                  6. 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 Link_out
                  7. 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 Link_out
                  8. 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 Link_out
                  9. 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 Link_out
                  10. 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 Link_out
                  11. 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 Link_out
                  12. 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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out
                  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 Link_out

                  Enzymes
                  Name: Amine oxidase [flavin-containing] B
                  Reactions:
                  Epinephrine + Water + Oxygen unknown 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxide details
                  Gene Name: MAOB
                  Uniprot ID: P27338 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Amine oxidase [flavin-containing] A
                  Reactions:
                  Epinephrine + Water + Oxygen unknown 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxide details
                  Gene Name: MAOA
                  Uniprot ID: P21397 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Catechol O-methyltransferase
                  Reactions:
                  S-Adenosylmethionine + Epinephrine unknown S-Adenosylhomocysteine + Metanephrine details
                  Gene Name: COMT
                  Uniprot ID: P21964 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Phenylalanine-4-hydroxylase
                  Reactions: Not Available
                  Gene Name: PAH
                  Uniprot ID: P00439 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Phenylethanolamine N-methyltransferase
                  Reactions:
                  S-Adenosylmethionine + Norepinephrine unknown S-Adenosylhomocysteine + Epinephrine details
                  Gene Name: PNMT
                  Uniprot ID: P11086 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Alpha-2A adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRA2A
                  Uniprot ID: P08913 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Alpha-2B adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRA2B
                  Uniprot ID: P18089 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Beta-1 adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRB1
                  Uniprot ID: P08588 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Beta-2 adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRB2
                  Uniprot ID: P07550 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Alpha-1A adrenergic receptor
                  Reactions: Not Available
                  Gene Name: ADRA1A
                  Uniprot ID: P35348 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Trace amine-associated receptor 1
                  Reactions: Not Available
                  Gene Name: TAAR1
                  Uniprot ID: Q96RJ0 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA