Epinephrine (CED0000785)

Record Information
Version1.0
Creation Date2016-05-19 01:30:30 UTC
Update Date2026-05-14 16:45:33 UTC
Accession NumberCHEM003955
Identification
Common NameEpinephrine
ClassSmall Molecule
Description
Epinephrine (C9H13NO3) is an organic compound with an average molecular weight of 183.20 g/mol. Epinephrine belongs to the benzenediols, a subclass of phenols within the organic compounds. Biologically, it serves as a neurotransmitter (PMC11721280, PMC12293634, PMC2783905). It acts as an agonist/agonist or antagonist/antagonist for several protein targets, including the Alpha-1A adrenergic receptor (ADRA1A), Beta-1 adrenergic receptor (ADRB1), Beta-2 adrenergic receptor (ADRB2), Alpha-1B adrenergic receptor (ADRA1B), and four other proteins. The compound is released from or found in 43 recorded sources across multiple sectors. These include healthcare, pharmaceuticals & veterinary products (such as nasal preparations, cardiac stimulants excl. cardiac glycosides, drugs for obstructive airway diseases, stomatological preparations, and Vitamin k and other hemostatics); food, food processing & cookware (including food preservation, fermentation processes for beer, and the preparation of malt, vinegar, wine or sparkling wine); household cleaning & consumer products (such as bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites); electrical & electronic equipment (including amplifiers, antennas, coils, conductors or conductive bodies characterised by the conductive materials, and electric hearing aids); building & construction (tents or canopies, ladders, and ceilings); and indoor air. Recorded exposure routes include oral, intravenous, intramuscular, subcutaneous, inhalation, nasal, topical, sublingual, endotracheal, epidural, infiltration, intracardiac, intracaudal, intraocular, intraspinal, iontophoresis, ophthalmic, parenteral, perineural, periodontal, respiratory, retrobulbar, and submucosal. Epinephrine is used as a treatment for asthma (PMC11459094), shock (PMC10169116), hypotension (PMC7287907), and food allergy (PMC11037442). It has a therapeutic effect on bleeding (PMC7388630). Health associations include hypoglycemia (PMC6066785), tachycardia (PMC12193306), hypertension (PMC12193306, PMC8669078), an increase in blood pressure (PMC8983065), and an increase in fatigue (PMC11955606). Additionally, epinephrine is detected in urine in cases of pheochromocytoma (PMC1492602) and is decreased in blood in hypertension (PMC6720215).
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0a4i-3749000000-5e04477d54e6f4a1c444Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-014i-0900000000-092882ec13a2a213417eNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-014i-0900000000-02df1fed2290a4a8b149Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-1739000000-c4c544645b1cc7d3f564Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9300000000-d26f1ff13388b2105e30Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-007x-7019000000-286cfeb22dc15e202453Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-d7db96395ba5098c1b5cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-272a764c388aec241fafNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-1bbda1c632bd0ca4edbdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-0900000000-92937e3a48622f40baedNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0900000000-b00275b1e8611c273f02Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0k9l-7900000000-065763dae156017492c9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-45c50917c3f404f38e71Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-1900000000-713b357534dc0f81ae97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-5900000000-c6b1d16c9e7e36805557Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0900000000-12d3e633dd2bc4dd7070Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ri-2900000000-b797bd5890264522228dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ul4-9400000000-dfc3790bcb74b691d79eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-5901acff97ce4c2c0a86Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00ei-0900000000-84dd0413e6ecd127f640Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-059f-9800000000-dcfed53f641ae95f4779Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
216.0Log mg/kg[120:380]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
hypertensionassociated_withNot AvailablePMC12193306 , PMC8669078
hypertensiondecreased_in_blood_inNot AvailablePMC6720215
blood pressureassociated_withincreasePMC8983065
fatigueassociated_withincreasePMC11955606
asthmais_treatment_forNot AvailablePMC11459094
bleedinghas_therapeutic_effect_onNot AvailablePMC7388630
pheochromocytomadetected_in_urine_inNot AvailablePMC1492602
hypoglycemiaassociated_withNot AvailablePMC6066785
Food allergyis_treatment_forNot AvailablePMC11037442
hypotensionis_treatment_forNot AvailablePMC7287907
shockis_treatment_forNot AvailablePMC10169116
tachycardiaassociated_withNot AvailablePMC12193306
chronic asthmais_treatment_forNot AvailablePMC11037442
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
233BrushesPersonal care & cosmeticsNot Available
241Stomatological preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
275Vitamin k and other hemostaticsHealthcare, pharmaceuticals & veterinary productsNot Available
286Cardiac stimulants excl. cardiac glycosidesHealthcare, pharmaceuticals & veterinary productsNot Available
389Nasal preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
391Drugs for obstructive airway diseasesHealthcare, pharmaceuticals & veterinary productsNot Available
398Antiglaucoma preparations and mioticsHealthcare, pharmaceuticals & veterinary productsNot Available
495CeilingsBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
573Key RingsHousehold itemsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
624Merry Go RoundsRecreation & sports surfacesNot Available
629SwingsRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
655Slide FastenersTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
34 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Beta-2 adrenergic receptor structureClick to view 3D structureBeta-2 adrenergic receptorP07550HumansPredicted (SEA)0.155698
Click to view 3D structureBeta-1 adrenergic receptorB0FL73Cavia porcellusPredicted (SEA)0.389246
Click to view 3D structureTaste receptor type 2 member 50P59544HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 45P59539HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 42Q7RTR8HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 41P59536HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 7Q9NYW3HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 30P59541HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 60P59551HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 19P59542HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 20P59543HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 1Q9NYW7HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 40P59535HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 3Q9NYW6HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 13Q9NYV9HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 39P59534HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 5Q9NYW4HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 9Q9NYW1HumansPredicted (SEA)0.0778492
Click to view 3D structureTaste receptor type 2 member 43P59537HumansPredicted (SEA)0.0778492
Click to view 3D structureBeta-2 adrenergic receptorQ8K4Z4Cavia porcellusPredicted (SEA)0.155698
Beta-3 adrenergic receptor structureClick to view 3D structureBeta-3 adrenergic receptorP13945HumansPredicted (SEA)0.389246
Beta-1 adrenergic receptor structureClick to view 3D structureBeta-1 adrenergic receptorP08588HumansPredicted (SEA)0.622794
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)2.80257
Click to view 3D structureBeta-1 adrenergic receptorP18090Rattus norvegicusPredicted (SEA)0.467095
Click to view 3D structureBeta-2 adrenergic receptorP54833Canis lupus familiarisPredicted (SEA)0.0778492
Concentrations
Not Available
External Links
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