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Epinephrine (CHEM003955)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 01:30:30 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003955
Identification
Common NameEpinephrine
ClassSmall Molecule
DescriptionA catecholamine in which the aminoethyl side-chain is hydroxy-substituted at C-1 and methylated on nitrogen.
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-AdrenalineChEBI
(+-)-EpinephrineChEBI
2-(Methylamino)-1-(3,4-dihydroxyphenyl)ethanolChEBI
DL-AdrenalineChEBI
Epinephrine racemicChEBI
RacepinefrinaChEBI
RacepinefrineChEBI
RacepinefrinumChEBI
Epinephrine, racemic mixtureHMDB
Hydrochloride, racepinephrineHMDB
Mixture epinephrine, racemicHMDB
Adrenaline, racemic mixtureHMDB
MicronefrinHMDB
Mixture adrenaline, racemicHMDB
Racemic mixture adrenalineHMDB
RacepinephrineHMDB
VaponefrinHMDB
Adrenaline, racemicHMDB
Bird brand OF racepinefrine hydrochlorideHMDB
Epinephrine hydrochloride, racemic mixtureHMDB
Racemic adrenalineHMDB
Racemic mixture epinephrineHMDB
Adrenaline hydrochloride, racemic mixtureHMDB
Epinephrine, racemicHMDB
MicronephrineHMDB
Racemic epinephrineHMDB
Racepinephrine hydrochlorideHMDB
Chemical FormulaC9H13NO3
Average Molecular Mass183.204 g/mol
Monoisotopic Mass183.090 g/mol
CAS Registry Number51-43-4
IUPAC Name4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
Traditional Name(+-)-adrenaline
SMILESCNCC(O)C1=CC(O)=C(O)C=C1
InChI IdentifierInChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3
InChI KeyUCTWMZQNUQWSLP-UHFFFAOYSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Polarizability18.89 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4i-3749000000-5e04477d54e6f4a1c444View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-014i-0900000000-092882ec13a2a213417eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014i-0900000000-02df1fed2290a4a8b149View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0a4i-1739000000-c4c544645b1cc7d3f564View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0006-9300000000-d26f1ff13388b2105e30View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS)splash10-007x-7019000000-286cfeb22dc15e202453View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2)Not Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3)Not Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-d7db96395ba5098c1b5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0900000000-272a764c388aec241fafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-1bbda1c632bd0ca4edbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0900000000-92937e3a48622f40baedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-b00275b1e8611c273f02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k9l-7900000000-065763dae156017492c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-45c50917c3f404f38e71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01q9-1900000000-713b357534dc0f81ae97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-c6b1d16c9e7e36805557View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0900000000-12d3e633dd2bc4dd7070View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00ri-2900000000-b797bd5890264522228dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ul4-9400000000-dfc3790bcb74b691d79eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-5901acff97ce4c2c0a86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ei-0900000000-84dd0413e6ecd127f640View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059f-9800000000-dcfed53f641ae95f4779View in MoNA
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0062515
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEpinephrine
Chemspider ID815
ChEBI ID33568
PubChem Compound ID838
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10052027
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24252294
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24719616