Canmetcon
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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
DescriptionPHYSICAL DESCRIPTION: Odorless light brown or nearly white crystals. (NTP, 1992)
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
(+-)-AdrenalineChEBI
(+-)-EpinephrineChEBI
2-(methylamino)-1-(3,4-Dihydroxyphenyl)ethanolChEBI
DL-AdrenalineChEBI
Epinephrine racemicChEBI
RacepinefrinaChEBI
RacepinefrineChEBI
RacepinefrinumChEBI
Epinephrine, racemic mixtureMeSH
Hydrochloride, racepinephrineMeSH
Mixture epinephrine, racemicMeSH
Adrenaline, racemic mixtureMeSH
MicronefrinMeSH
Mixture adrenaline, racemicMeSH
Racemic mixture adrenalineMeSH
RacepinephrineMeSH
VaponefrinMeSH
Adrenaline, racemicMeSH
Bird brand OF racepinefrine hydrochlorideMeSH
Epinephrine hydrochloride, racemic mixtureMeSH
Racemic adrenalineMeSH
Racemic mixture epinephrineMeSH
Adrenaline hydrochloride, racemic mixtureMeSH
Epinephrine, racemicMeSH
MicronephrineMeSH
Racemic epinephrineMeSH
Racepinephrine hydrochlorideMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as catechols. These are compounds containing a 1,2-benzenediol moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
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 mg/mLALOGPS
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
Polarizability18.89 Å3ChemAxon
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
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot 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 IDNot Available
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 IDNot Available
ChEBI ID33568
PubChem Compound ID838
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. http://www.ncbi.nlm.nih.gov/pubmed/?term=10052027
2. http://www.ncbi.nlm.nih.gov/pubmed/?term=24252294
3. http://www.ncbi.nlm.nih.gov/pubmed/?term=24719616