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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:38:54 UTC
NP-MRD IDNP0000300
Secondary Accession NumbersNone
Natural Product 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
ValueSource
(-)-(R)-EpinephrineChEBI
(-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcoholChEBI
(-)-AdrenalineChEBI
(R)-(-)-AdrenalineChEBI
(R)-(-)-AdnephrineChEBI
(R)-(-)-EpinephrineChEBI
(R)-(-)-EpirenamineChEBI
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediolChEBI
AdrenalinChEBI
AdrenalineChEBI
EpinefrinaChEBI
EpinephrinChEBI
EpinephrinumChEBI
EpipenChEBI
Epipen JRChEBI
L-AdrenalineChEBI
LevoepinephrineChEBI
PrimateneChEBI
Auvi-QKegg
(-)-3,4-Dihydroxy-a-((methylamino)methyl)benzyl alcoholGenerator
(-)-3,4-Dihydroxy-α-((methylamino)methyl)benzyl alcoholGenerator
(-)-3,4-Dihydroxy-a-[(methylamino)methyl]-benzyl alcoholHMDB
(-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcoholHMDB
(-)-3,4-Dihydroxy-alpha-[(methylamino)methyl]-benzyl alcoholHMDB
(-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcoholHMDB
(-)-EpinephrineHMDB
(R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediolHMDB
(R)-AdrenalineHMDB
(R)-EpinephrineHMDB
AdnephrineHMDB
AdrenalHMDB
AdrenineHMDB
AdrinHMDB
Ana-kitHMDB
BosminHMDB
Bronkaid mistHMDB
ChelafrinHMDB
EpifrinHMDB
EpiglaufrinHMDB
EpinephranHMDB
EpirenanHMDB
EppyHMDB
ExadrinHMDB
GlauposineHMDB
HemisineHMDB
HemostasinHMDB
HemostatinHMDB
HypernephrinHMDB
IsoptoepinalHMDB
L-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanolHMDB
L-EpinephrineHMDB
L-EpirenamineHMDB
L-MethylaminoethanolcatecholHMDB
LevorenenHMDB
LevoreninHMDB
LevorenineHMDB
LevoreninumHMDB
LyodrinHMDB
MethylarterenolHMDB
MucidrinaHMDB
NephridineHMDB
NieralineHMDB
ParanephrinHMDB
Primatene mistHMDB
R-(-)-EpinephrineHMDB
RenaglandinHMDB
RenaleptineHMDB
RenalinaHMDB
RenoformHMDB
RenostypticinHMDB
RenostyptinHMDB
ScurenalineHMDB
SimpleneHMDB
StyptirenalHMDB
SupracapsulinHMDB
SupranephraneHMDB
SuprarenalineHMDB
SuprareninHMDB
SurrenineHMDB
Sus-phrineHMDB
TakaminaHMDB
VasoconstrictineHMDB
VasotoninHMDB
4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediolHMDB
Epinephrine bitartrateHMDB
Epinephrine hydrogen tartrateHMDB
LyophrinHMDB
Adrenaline bitartrateHMDB
Adrenaline hydrochlorideHMDB
Epinephrine acetateHMDB
Allergan brand OF adrenaline hydrochlorideHMDB
EpitrateHMDB
Acetate, epinephrineHMDB
Adrenaline acid tartrateHMDB
Epinephrine hydrochlorideHMDB
Medihaler-epiHMDB
Chemical FormulaC9H13NO3
Average Mass183.2044 Da
Monoisotopic Mass183.08954 Da
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(O)=C(O)C=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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica olereaceaPlant
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
ColumbaFooDB
ColumbidaeFooDB
Crataegus rhipidophyllaLOTUS Database
Cytisus copariusPlant
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Hemidesmus indicusLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Persea americanaFooDB
    • F. W. Knapp. Some Characteristics of Eggplant and Avocado Poiyphenolases. J. Food Science. 30(6),...
Phaseolus vulgarisPlant
PhasianidaeFooDB
Phasianus colchicusFooDB
Pisum sativumPlant
Portulaca grandifloraPlant
Scoparia dulcisPlant
Solanum lycopersicumPlant
Solanum melanogenaPlant
Solanum melongenaFooDB
    • F. W. Knapp. Some Characteristics of Eggplant and Avocado Poiyphenolases. J. Food Science. 30(6),...
Spinacia oleraceaPlant
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vicia fabaPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Aromatic alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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. and Leo, A. Pomona College Medicinal Chemistry Project Claremont, CA Pomona College, July 1987. Log P Database, (C. Hansch and A. Leo), July 1987 edition.
Predicted Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.23 m³·mol⁻¹ChemAxon
Polarizability19.04 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000068
DrugBank IDDB00668
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021889
KNApSAcK IDC00029643
Chemspider ID5611
KEGG Compound IDC00788
BioCyc IDL-EPINEPHRINE
BiGG ID35997
Wikipedia LinkEpinephrine
METLIN ID5127
PubChem Compound5816
PDB IDNot Available
ChEBI ID28918
Good Scents IDNot Available
References
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 ]