CHEBI:28918 - (R)-adrenaline

ChEBI IDCHEBI:28918
ChEBI Name(R)-adrenaline
Stars
ASCII Name(R)-adrenaline
DefinitionThe R-enantiomer of adrenaline. It is a hormone secreted by the adrenal glands resulting in the 'fight-or-flight' response.
Secondary ChEBI IDsCHEBI:1942, CHEBI:23928
Last Modified5 April 2023
DownloadsMolfile
FormulaC9H13NO3
Net Charge0
Average Mass183.207
Monoisotopic Mass183.08954
SMILESCNC[C@H](O)c1ccc(O)c(O)c1
InChIInChI=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
InChIKeyUCTWMZQNUQWSLP-VIFPVBQESA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Mus musculus (ncbitaxon:10090) - PubMed (19425150) Source: BioModels - MODEL1507180067
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
hormone  Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
beta-adrenergic agonist  An agent that selectively binds to and activates β-adrenergic receptors.
alpha-adrenergic agonist  An agent that selectively binds to and activates α-adrenergic receptors.
sympathomimetic agent  A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
adrenergic agonist  An agent that selectively binds to and activates adrenergic receptors.
mouse metabolite  Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
Applications:
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
vasodilator agent  A drug used to cause dilation of the blood vessels.
bronchodilator agent  An agent that causes an increase in the expansion of a bronchus or bronchial tubes.
beta-adrenergic agonist  An agent that selectively binds to and activates β-adrenergic receptors.
vulnerary  A drug used in treating and healing of wounds.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
alpha-adrenergic agonist  An agent that selectively binds to and activates α-adrenergic receptors.
sympathomimetic agent  A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.
anti-allergic agent  A drug used to treat allergic reactions.
hypoglycemic agent  A drug which lowers the blood glucose level.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
vasoconstrictor agent  Drug used to cause constriction of the blood vessels.
adrenergic agonist  An agent that selectively binds to and activates adrenergic receptors.
antispasmodic drug  A drug that suppresses spasms. These are usually caused by smooth muscle contraction, especially in tubular organs. The effect is to prevent spasms of the stomach, intestine or urinary bladder.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
nasal decongestant  A drug used to relieve nasal congestion in the upper respiratory tract.
mydriatic agent  Agent that dilates the pupil. Used in eye diseases and to facilitate eye examination. It may be either a sympathomimetic or parasympatholytic. The latter cause cycloplegia or paralysis of accommodation at high doses and may precipitate glaucoma.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
anti-asthmatic agent  Any compound that has anti-asthmatic effects.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
antiglaucoma drug  Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
anti-arrhythmia drug  A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
ChEBI Ontology
Outgoing Relation(s)
(R)-adrenaline (CHEBI:28918) has role adrenergic agonist (CHEBI:37886)
(R)-adrenaline (CHEBI:28918) has role analgesic (CHEBI:35480)
(R)-adrenaline (CHEBI:28918) has role anti-allergic agent (CHEBI:50857)
(R)-adrenaline (CHEBI:28918) has role anti-arrhythmia drug (CHEBI:38070)
(R)-adrenaline (CHEBI:28918) has role anti-asthmatic agent (CHEBI:65023)
(R)-adrenaline (CHEBI:28918) has role anti-inflammatory agent (CHEBI:67079)
(R)-adrenaline (CHEBI:28918) has role antidepressant (CHEBI:35469)
(R)-adrenaline (CHEBI:28918) has role antiglaucoma drug (CHEBI:39456)
(R)-adrenaline (CHEBI:28918) has role antiinfective agent (CHEBI:35441)
(R)-adrenaline (CHEBI:28918) has role antineoplastic agent (CHEBI:35610)
(R)-adrenaline (CHEBI:28918) has role antispasmodic drug (CHEBI:53784)
(R)-adrenaline (CHEBI:28918) has role bronchodilator agent (CHEBI:35523)
(R)-adrenaline (CHEBI:28918) has role cardiovascular drug (CHEBI:35554)
(R)-adrenaline (CHEBI:28918) has role hormone (CHEBI:24621)
(R)-adrenaline (CHEBI:28918) has role hypoglycemic agent (CHEBI:35526)
(R)-adrenaline (CHEBI:28918) has role mouse metabolite (CHEBI:75771)
(R)-adrenaline (CHEBI:28918) has role mydriatic agent (CHEBI:50513)
(R)-adrenaline (CHEBI:28918) has role nasal decongestant (CHEBI:77715)
(R)-adrenaline (CHEBI:28918) has role sympathomimetic agent (CHEBI:35524)
(R)-adrenaline (CHEBI:28918) has role vasoconstrictor agent (CHEBI:50514)
(R)-adrenaline (CHEBI:28918) has role vasodilator agent (CHEBI:35620)
(R)-adrenaline (CHEBI:28918) has role vulnerary (CHEBI:73336)
(R)-adrenaline (CHEBI:28918) has role α-adrenergic agonist (CHEBI:35569)
(R)-adrenaline (CHEBI:28918) has role β-adrenergic agonist (CHEBI:35522)
(R)-adrenaline (CHEBI:28918) is a 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol (CHEBI:194548)
(R)-adrenaline (CHEBI:28918) is conjugate base of (R)-adrenaline(1+) (CHEBI:71406)
(R)-adrenaline (CHEBI:28918) is enantiomer of (S)-adrenaline (CHEBI:40751)
Incoming Relation(s)
(R)-adrenaline hydrochloride (CHEBI:6213) has part (R)-adrenaline (CHEBI:28918)
adrenaline (CHEBI:33568) has part (R)-adrenaline (CHEBI:28918)
(R)-adrenaline(1+) (CHEBI:71406) is conjugate acid of (R)-adrenaline (CHEBI:28918)
(S)-adrenaline (CHEBI:40751) is enantiomer of (R)-adrenaline (CHEBI:28918)
IUPAC Name 
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
INNs  Source
epinefrinaChemIDplus
epinephrineChemIDplus
épinéphrineChEBI
epinephrinumChemIDplus
Synonyms  Source
(−)-3,4-dihydroxy-α-((methylamino)methyl)benzyl alcoholNIST Chemistry WebBook
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediolKEGG COMPOUND
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediolKEGG COMPOUND
AdrenalinNIST Chemistry WebBook
(−)-adrenalineIUPHAR
adrenalineNIST Chemistry WebBook
Brand Names  Source
AdrenaclickChEMBL
AdrenalinKEGG DRUG
Adren coChEMBL
Ana-guardChEMBL
AnapenChEMBL
Anaphylactic shock drug kitChEMBL
Manual XrefsDatabases
1028DrugCentral
C00029643KNApSAcK
C00788KEGG COMPOUND
D00095KEGG DRUG
DB00668DrugBank
EpinephrineWikipedia
HMDB0000068HMDB
L-EPINEPHRINEMetaCyc
Registry NumbersSources
Reaxys:2368277Reaxys
CAS:51-43-4KEGG COMPOUND
CAS:51-43-4ChemIDplus
CAS:51-43-4NIST Chemistry WebBook
Citations