ChemFOnt: Showing chemical card for Epinephrine (CFc000000048)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:20 UTC

Chemfont ID

CFc000000048

Molecule Identification

Common Name

Epinephrine

Definition

Epinephrine 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-(R)-Epinephrine	ChEBI
(-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol	ChEBI
(-)-Adrenaline	ChEBI
(R)-(-)-Adrenaline	ChEBI
(R)-(-)-Adnephrine	ChEBI
(R)-(-)-Epinephrine	ChEBI
(R)-(-)-Epirenamine	ChEBI
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol	ChEBI
Adrenalin	ChEBI
Adrenaline	ChEBI
Epinefrina	ChEBI
Epinephrin	ChEBI
Epinephrinum	ChEBI
Epipen	ChEBI
Epipen JR	ChEBI
L-Adrenaline	ChEBI
Levoepinephrine	ChEBI
Primatene	ChEBI
Auvi-Q	Kegg
(-)-3,4-Dihydroxy-a-((methylamino)methyl)benzyl alcohol	Generator
(-)-3,4-Dihydroxy-α-((methylamino)methyl)benzyl alcohol	Generator
(-)-3,4-Dihydroxy-a-[(methylamino)methyl]-benzyl alcohol	HMDB
(-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol	HMDB
(-)-3,4-Dihydroxy-alpha-[(methylamino)methyl]-benzyl alcohol	HMDB
(-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol	HMDB
(-)-Epinephrine	HMDB
(R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol	HMDB
(R)-Adrenaline	HMDB
(R)-Epinephrine	HMDB
Adnephrine	HMDB
Adrenal	HMDB
Adrenine	HMDB
Adrin	HMDB
Ana-kit	HMDB
Bosmin	HMDB
Bronkaid mist	HMDB
Chelafrin	HMDB
Epifrin	HMDB
Epiglaufrin	HMDB
Epinephran	HMDB
Epirenan	HMDB
Eppy	HMDB
Exadrin	HMDB
Glauposine	HMDB
Hemisine	HMDB
Hemostasin	HMDB
Hemostatin	HMDB
Hypernephrin	HMDB
Isoptoepinal	HMDB
L-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol	HMDB
L-Epinephrine	HMDB
L-Epirenamine	HMDB
L-Methylaminoethanolcatechol	HMDB
Levorenen	HMDB
Levorenin	HMDB
Levorenine	HMDB
Levoreninum	HMDB
Lyodrin	HMDB
Methylarterenol	HMDB
Mucidrina	HMDB
Nephridine	HMDB
Nieraline	HMDB
Paranephrin	HMDB
Primatene mist	HMDB
R-(-)-Epinephrine	HMDB
Renaglandin	HMDB
Renaleptine	HMDB
Renalina	HMDB
Renoform	HMDB
Renostypticin	HMDB
Renostyptin	HMDB
Scurenaline	HMDB
Simplene	HMDB
Styptirenal	HMDB
Supracapsulin	HMDB
Supranephrane	HMDB
Suprarenaline	HMDB
Suprarenin	HMDB
Surrenine	HMDB
Sus-phrine	HMDB
Takamina	HMDB
Vasoconstrictine	HMDB
Vasotonin	HMDB
4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol	HMDB
Epinephrine bitartrate	HMDB
Epinephrine hydrogen tartrate	HMDB
Lyophrin	HMDB
Adrenaline bitartrate	HMDB
Adrenaline hydrochloride	HMDB
Epinephrine acetate	HMDB
Allergan brand OF adrenaline hydrochloride	HMDB
Epitrate	HMDB
Acetate, epinephrine	HMDB
Adrenaline acid tartrate	HMDB
Epinephrine hydrochloride	HMDB
Medihaler-epi	HMDB

Chemical Formula

C₉H₁₃NO₃

Average Molecular Weight

183.2044

Monoisotopic Molecular Weight

183.089543287

IUPAC Name

4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

Traditional Name

epinephrine

CAS Registry Number

51-43-4

SMILES

CNC[C@H](O)C1=CC(O)=C(O)C=C1

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 Key

UCTWMZQNUQWSLP-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

adrenaline (CHEBI:28918 )
Biogenic amines (C00788 )
Adrenalines (C00788 )

Functional Ontology

Physiological effect

Health effect

Circulatory system disorder

Blood and lymphatic system disorder

Hemorrhagic disorder

Subarachnoid hemorrhage (HMDB: HMDB0000068)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000068)

Traumatic brain injury (HMDB: HMDB0000068)

Endocrine system disorder

Adrenal disorder

Pheochromocytoma (HMDB: HMDB0000068)
Addison's Disease (HMDB: HMDB0000068)

Adipose tissue (HMDB: HMDB0000068)
Adipose tissue (HMDB: HMDB0000068)

Nervous tissue

Nervous tissue (HMDB: HMDB0000068)

Epithelium

Epidermis (HMDB: HMDB0000068)

Eye Lens (HMDB: HMDB0000068)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000068)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7704967)
Cerebrospinal Fluid (CSF) (PMID: 12834252)
Cerebrospinal fluid (HMDB: HMDB0000068)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000068)

Hematocyte

Platelet (HMDB: HMDB0000068)

Tissue substructure

Muscle (HMDB: HMDB0000068)

Organ substructure

Organ

Gland

Adrenal Gland (HMDB: HMDB0000068)
Adrenal Gland (HMDB: HMDB0000068)

Excreta

Biofluid or Excreta

Urine (PMID: 10349032)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0000068)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)

Endogenous

Endogenous (HMDB: HMDB0000068)

Microbe

Escherichia coli (HMDB: HMDB0000068)
Bacillus (HMDB: HMDB0000068)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0087328)
Catecholamine Biosynthesis (HMDB: HMDB0000068)
Catecholamine Biosynthesis (PathBank: SMP0063606)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Aromatic L-Aminoacid Decarboxylase Deficiency (PathBank: SMP0120457)
Tyrosine Hydroxylase Deficiency (PathBank: SMP0120562)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (HMDB: HMDB0000068)
Disulfiram Action Pathway (PathBank: SMP0000429)
Epinephrine Action Pathway (PathBank: SMP0000661)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000068)

Biomarker

Addison's Disease (MarkerDB: MDB00000035)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	18.6 g/L	ALOGPS
logP	-0.82	ALOGPS
logP	-0.43	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	9.69	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.23 m³·mol⁻¹	ChemAxon
Polarizability	19.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000068

DrugBank ID

DB00668

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28918

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Singer, 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.

Showing chemical card for Epinephrine (CFc000000048)

MOL for CFc000000048 (Epinephrine)

3D MOL for CFc000000048 (Epinephrine)

3D SDF for CFc000000048 (Epinephrine)

3D-SDF for CFc000000048 (Epinephrine)

PDB for CFc000000048 (Epinephrine)

3D PDB for CFc000000048 (Epinephrine)

SMILES for CFc000000048 (Epinephrine)

INCHI for CFc000000048 (Epinephrine)

Structure for CFc000000048 (Epinephrine)

3D Structure for CFc000000048 (Epinephrine)