CHEBI:28918 - (R)-adrenaline

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (R)-adrenaline
ChEBI ID CHEBI:28918
ChEBI ASCII Name (R)-adrenaline
Definition The R-enantiomer of adrenaline. It is a hormone secreted by the adrenal glands resulting in the 'fight-or-flight' response.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:1942, CHEBI:23928
Supplier Information ChemicalBook:CB5853720, ChemicalBook:CB82551184, eMolecules:532436, Selleckchem:l-thyroxine, ZINC000003830993
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Levothyroxine, also known as L-thyroxine, is a synthetic form of the thyroid hormone thyroxine (T4). It is used to treat thyroid hormone deficiency (hypothyroidism), including a severe form known as myxedema coma. It may also be used to treat and prevent certain types of thyroid tumors. It is not indicated for weight loss. Levothyroxine is taken orally (by mouth) or given by intravenous injection. Levothyroxine has a half-life of 7.5 days when taken daily, so about six weeks is required for it to reach a steady level in the blood. Side effects from excessive doses include weight loss, trouble tolerating heat, sweating, anxiety, trouble sleeping, tremor, and fast heart rate. Use is not recommended in people who have had a recent heart attack. Use during pregnancy has been found to be safe. Dosing should be based on regular measurements of thyroid-stimulating hormone (TSH) and T4 levels in the blood. Much of the effect of levothyroxine is following its conversion to triiodothyronine (T3). Levothyroxine was first made in 1927. It is on the World Health Organization's List of Essential Medicines. Levothyroxine is available as a generic medication. In 2022, it was the fourth most commonly prescribed medication in the United States, with more than 82 million prescriptions.
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Formula C9H13NO3
Net Charge 0
Average Mass 183.20440
Monoisotopic Mass 183.08954
InChI 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
InChIKey UCTWMZQNUQWSLP-VIFPVBQESA-N
SMILES CNC[C@H](O)c1ccc(O)c(O)c1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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).
alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
beta-adrenergic agonist
An agent that selectively binds to and activates beta-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.
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.
molecular messenger

(via monoamine molecular messenger )
Application(s): adrenergic agonist
An agent that selectively binds to and activates adrenergic receptors.
vasodilator agent
A drug used to cause dilation of the blood vessels.
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.
bronchodilator agent
An agent that causes an increase in the expansion of a bronchus or bronchial tubes.
alpha-adrenergic agonist
An agent that selectively binds to and activates alpha-adrenergic receptors.
vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
beta-adrenergic agonist
An agent that selectively binds to and activates beta-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.
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ChEBI Ontology
Outgoing (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) has role adrenergic agonist (CHEBI:37886)
(R)-adrenaline (CHEBI:28918) has role bronchodilator agent (CHEBI:35523)
(R)-adrenaline (CHEBI:28918) has role hormone (CHEBI:24621)
(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 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) 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 (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 Sources
epinefrina ChemIDplus
epinephrine ChemIDplus
épinéphrine ChEBI
epinephrinum ChemIDplus
Synonyms Sources
(−)-(R)-epinephrine ChemIDplus
(−)-3,4-dihydroxy-α-((methylamino)methyl)benzyl alcohol NIST Chemistry WebBook
(−)-adrenaline IUPHAR
(R)-(−)-adrenaline ChEBI
(R)-(-)-Adnephrine KEGG COMPOUND
(R)-(-)-Adrenaline KEGG COMPOUND
(R)-(-)-Epinephrine KEGG COMPOUND
(R)-(-)-Epirenamine KEGG COMPOUND
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol KEGG COMPOUND
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol KEGG COMPOUND
Adrenalin NIST Chemistry WebBook
adrénaline ChEBI
adrenaline NIST Chemistry WebBook
Epinephrin ChEBI
L-Adrenaline KEGG COMPOUND
levoepinephrine IUPHAR
Brand Names Sources
Adrenalin KEGG DRUG
Epipen DrugBank
Epipen KEGG DRUG
Epipen JR DrugBank
Primatene DrugBank
Manual Xrefs Databases
1028 DrugCentral
C00029643 KNApSAcK
C00788 KEGG COMPOUND
D00095 KEGG DRUG
DB00668 DrugBank
Epinephrine Wikipedia
HMDB0000068 HMDB
L-EPINEPHRINE MetaCyc
View more database links
Registry Numbers Types Sources
2368277 Reaxys Registry Number Reaxys
51-43-4 CAS Registry Number KEGG COMPOUND
51-43-4 CAS Registry Number ChemIDplus
51-43-4 CAS Registry Number NIST Chemistry WebBook
Citations Types Sources
18325983 PubMed citation Europe PMC
21963816 PubMed citation Europe PMC
22115931 PubMed citation Europe PMC
22405854 PubMed citation Europe PMC
22425731 PubMed citation Europe PMC
22429969 PubMed citation Europe PMC
22569014 PubMed citation Europe PMC
22623754 PubMed citation Europe PMC
22826982 PubMed citation Europe PMC
22895980 PubMed citation Europe PMC
22898765 PubMed citation Europe PMC
22905594 PubMed citation Europe PMC
22940899 PubMed citation Europe PMC
23066296 PubMed citation Europe PMC
23130169 PubMed citation Europe PMC
23164182 PubMed citation Europe PMC
23185846 PubMed citation Europe PMC
29438107 PubMed citation Europe PMC
Last Modified
05 April 2023