Survey with prize
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Record Information
Version1.0
Creation Date2016-09-30 22:19:14 UTC
Update Date2020-05-21 16:28:47 UTC
BMDB IDBMDB0000068
Secondary Accession Numbers
  • BMDB00068
Metabolite Identification
Common NameEpinephrine
DescriptionEpinephrinee, also known as epinephrinee or epinephrine, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Epinephrinee exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Epinephrinee exists in all living organisms, ranging from bacteria to humans. Epinephrinee participates in a number of enzymatic reactions, within cattle. In particular, S-Adenosylhomocysteine and epinephrinee can be biosynthesized from S-adenosylmethionine and norepinephrinee through its interaction with the enzyme phenylethanolamine N-methyltransferase. In addition, Epinephrinee can be converted into 3,4-dihydroxymandelaldehyde and methylamine; which is catalyzed by the enzyme amine oxidase [flavin-containing] a. In cattle, epinephrinee is involved in the metabolic pathway called the tyrosine metabolism pathway.
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 Molecular Weight183.2044
Monoisotopic Molecular Weight183.089543287
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number51-43-4
SMILESNot Available
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
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Myelin sheath
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 & LEO,AJ (1985)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Myelin sheath
Biospecimen Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Epidermis
  • Eye Lens
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Mammary Gland
  • Neuron
  • Ovary
  • Pancreas
  • Placenta
  • Platelet
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal CortexExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Adrenal MedullaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BladderExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Eye LensExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
OvaryExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PancreasExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000068
DrugBank IDDB00668
Phenol Explorer Compound IDNot Available
FooDB IDFDB021889
KNApSAcK IDC00029643
Chemspider ID5611
KEGG Compound IDC00788
BioCyc IDL-EPINEPHRINE
BiGG ID35997
Wikipedia LinkEpinephrine
METLIN ID5127
PubChem Compound5816
PDB IDNot Available
ChEBI ID28918
References
Synthesis ReferenceSinger, Robert A.; Carreira, Erick M. An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine. Tetrahedron Letters (1997), 38(6), 927-930.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in the biosynthesis of adrenal corticoids. Catalyzes the hydroxylation of carbon hydrogen bond at 11-beta position of 11-deoxycortisol and 11-deoxycorticosterone/21-hydroxyprogesterone yielding cortisol or corticosterone, respectively. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin).
Gene Name:
CYP11B1
Uniprot ID:
P15150
Molecular weight:
57847.0
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the side-chain hydroxylation and cleavage of cholesterol to pregnenolone, the precursor of most steroid hormones (PubMed:11412116). Catalyzes three sequential oxidation reactions of cholesterol, namely the hydroxylation at C22 followed with the hydroxylation at C20 to yield 20R,22R-hydroxycholesterol that is further cleaved between C20 and C22 to yield the C21-steroid pregnenolone and 4-methylpentanal (PubMed:11412116). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11412116).
Gene Name:
CYP11A1
Uniprot ID:
P00189
Molecular weight:
60333.0
General function:
Involved in phenylethanolamine N-methyltransferase acti
Specific function:
Converts noradrenaline to adrenaline.
Gene Name:
PNMT
Uniprot ID:
P10938
Molecular weight:
30918.0
Reactions
S-Adenosylmethionine + Norepinephrine → S-Adenosylhomocysteine + Epinephrinedetails
General function:
Involved in catechol O-methyltransferase activity
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol (By similarity).
Gene Name:
COMT
Uniprot ID:
A7MBI7
Molecular weight:
30485.0
Reactions
Epinephrine + Guaiacol → Metanephrine + Pyrocatecholdetails
General function:
Amino acid transport and metabolism
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21398
Molecular weight:
59758.0
Reactions
Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxidedetails
General function:
Involved in prostaglandin E receptor activity
Specific function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. Has a relaxing effect on smooth muscle. May play an important role in regulating renal hemodynamics, intestinal epithelial transport, adrenal aldosterone secretion, and uterine function (By similarity).
Gene Name:
PTGER4
Uniprot ID:
Q8MJ08
Molecular weight:
53298.0
General function:
Involved in vasoactive intestinal polypeptide receptor
Specific function:
This is a receptor for PACAP-27 and PACAP-38. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase. May regulate the release of adrenocorticotropin, luteinizing hormone, growth hormone, prolactin, epinephrine, and catecholamine. May play a role in spermatogenesis and sperm motility. Causes smooth muscle relaxation and secretion in the gastrointestinal tract (By similarity).
Gene Name:
ADCYAP1R1
Uniprot ID:
Q29627
Molecular weight:
58785.0
General function:
Involved in beta2-adrenergic receptor activity
Specific function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine (By similarity).
Gene Name:
ADRB2
Uniprot ID:
Q28044
Molecular weight:
47136.0
General function:
Not Available
Specific function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling (By similarity). Involved in the regulation of sleep/wake behaviors (By similarity).
Gene Name:
ADRB1
Uniprot ID:
Q9TT96
Molecular weight:
50137.0
General function:
Cell cycle control, cell division, chromosome partitioning
Specific function:
Transcriptional activator. Seems to be essential for sexual differentiation and formation of the primary steroidogenic tissues. Binds to the Ad4 site found in the promoter region of steroidogenic P450 genes such as CYP11A, CYP11B and CYP21B. Also regulates the AMH/Muellerian inhibiting substance gene as well as the AHCH and STAR genes. 5'-YCAAGGYC-3' and 5'-RRAGGTCA-3' are the consensus sequences for the recognition by NR5A1. The SFPQ-NONO-NR5A1 complex binds to the CYP17 promoter and regulates basal and cAMP-dependent transcriptional activity. Binds phospholipids with a phosphatidylinositol (PI) headgroup, in particular PI(3,4)P2 and PI(3,4,5)P3. Activated by the phosphorylation of NR5A1 by HIPK3 leading to increased steroidogenic gene expression upon cAMP signaling pathway stimulation (By similarity).
Gene Name:
NR5A1
Uniprot ID:
Q04752
Molecular weight:
51613.0