Record Information
Version1.0
Creation date2011-09-21 00:04:37 UTC
Update date2019-11-26 03:21:00 UTC
Primary IDFDB021889
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number51-43-4
Structure
Thumb
Synonyms
SynonymSource
(-)-(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
(-)-3,4-dihydroxy-a-[(methylamino)methyl]-Benzyl alcoholhmdb
(-)-3,4-dihydroxy-alpha-[(methylamino)methyl]-Benzyl alcoholhmdb
(R)-4-[1-hydroxy-2-(methylamino)ethyl]-1,2-Benzenediolhmdb
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-1,2-Benzenediolhmdb
Ana-Kithmdb
Bronkaid Misthmdb
Epinephrinehmdb
Epipen jrChEBI
l-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanolhmdb
l-Epinephrinehmdb
l-Epirenaminehmdb
Primatene Misthmdb
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
Chemical FormulaC9H13NO3
IUPAC name4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
InChI IdentifierInChI=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
Isomeric SMILESCNC[C@H](O)C1=CC(O)=C(O)C=C1
Average Molecular Weight183.2044
Monoisotopic Molecular Weight183.089543287
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSEpinephrine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-5ca773e378035e522e65Spectrum
GC-MSEpinephrine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-5ca773e378035e522e65Spectrum
Predicted GC-MSEpinephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9600000000-584d6e44f2be8cb4eeb1Spectrum
Predicted GC-MSEpinephrine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00si-7639000000-5bde61303f7506ecea58Spectrum
Predicted GC-MSEpinephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEpinephrine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0900000000-7718bec49c1a109083e52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-4900000000-ec5581e838e2a4a661392012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9200000000-4572448ba3dadff2d2a62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-001i-0900000000-9da12d9c8551de2507be2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-03di-0900000000-12dd42d00be1feb2ea6f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-0900000000-57c9bc614d9bbbfeed6b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00dj-0900000000-375b0df9797eb0a3db5f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0fdk-1900000000-04c230e802b08770ccd42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-014i-0900000000-b707acd2982b875d2b8a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-014i-0900000000-f35900548228729020322012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-1900000000-7d7916641e9f2b8c2a1d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0adi-8900000000-5bbc248c0ddc66e4fe402012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004i-9300000000-af8ce8ce2cdd535404e92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0159-0900000000-f2fafb87963f9f1c69602012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0uxr-2900000000-b54ca44315664cba912a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0udi-4900000000-881b25fed45874c66e132012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0ugi-9500000000-1fadd0dd0beb4816b39d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-004j-9000000000-61011b8f179c08d62b622012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0900000000-32c82b77af021d75c50c2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-92937e3a48622f40baed2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-b00275b1e8611c273f022017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9l-7900000000-065763dae156017492c92017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-45c50917c3f404f38e712017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-1900000000-713b357534dc0f81ae972017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-c6b1d16c9e7e368055572017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID5611
ChEMBL IDCHEMBL679
KEGG Compound IDC00788
Pubchem Compound ID5816
Pubchem Substance IDNot Available
ChEBI ID28918
Phenol-Explorer IDNot Available
DrugBank IDDB00668
HMDB IDHMDB00068
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35997
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDEpinephrine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Alpha-2A adrenergic receptorADRA2AP08913
Alpha-2B adrenergic receptorADRA2BP18089
Phenylalanine-4-hydroxylasePAHP00439
Beta-1 adrenergic receptorADRB1P08588
Beta-2 adrenergic receptorADRB2P07550
Pathways
NameSMPDB LinkKEGG Link
Catecholamine BiosynthesisSMP00012 map00350
Tyrosine MetabolismSMP00006 map00350
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference