CHEBI:4562 - dihydroergotamine

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ChEBI Name dihydroergotamine
ChEBI ID CHEBI:4562
Definition Ergotamine in which a single bond replaces the double bond between positions 9 and 10. A semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine, it is used (as the methanesulfonic or tartaric acid salts) for the treatment of migraine and orthostatic hypotension.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:4826, CHEBI:658566
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Formula C33H37N5O5
Net Charge 0
Average Mass 583.67740
Monoisotopic Mass 583.279
InChI InChI=1S/C33H37N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1
InChIKey LUZRJRNZXALNLM-JGRZULCMSA-N
SMILES [H][C@@]12Cc3c[nH]c4cccc(c34)[C@@]1([H])C[C@H](CN2C)C(=O)N[C@]1(C)O[C@]2(O)N([C@@H](Cc3ccccc3)C(=O)N3CCC[C@@]23[H])C1=O
Roles Classification
Biological Role(s): serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
dopamine agonist
A drug that binds to and activates dopamine receptors.
sympatholytic agent
Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): serotonergic agonist
An agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
dopamine agonist
A drug that binds to and activates dopamine receptors.
sympatholytic agent
Any compound which inhibits the postganglionic functioning of the sympathetic nervous system (SNS).
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ChEBI Ontology
Outgoing dihydroergotamine (CHEBI:4562) has role dopamine agonist (CHEBI:51065)
dihydroergotamine (CHEBI:4562) has role non-narcotic analgesic (CHEBI:35481)
dihydroergotamine (CHEBI:4562) has role serotonergic agonist (CHEBI:35941)
dihydroergotamine (CHEBI:4562) has role sympatholytic agent (CHEBI:66991)
dihydroergotamine (CHEBI:4562) has role vasoconstrictor agent (CHEBI:50514)
dihydroergotamine (CHEBI:4562) is a ergot alkaloid (CHEBI:23943)
dihydroergotamine (CHEBI:4562) is a semisynthetic derivative (CHEBI:72588)
Incoming dihydroergotamine mesylate (CHEBI:59756) has part dihydroergotamine (CHEBI:4562)
dihydroergotamine tartrate (CHEBI:59757) has part dihydroergotamine (CHEBI:4562)
IUPAC Name
(10αH)-5'α-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
INNs Sources
dihidroergotamina ChemIDplus
dihydroergotamine KEGG DRUG
dihydroergotaminum ChemIDplus
Synonyms Sources
5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman NIST Chemistry WebBook
9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione NIST Chemistry WebBook
9,10-dihydroergotamine ChemIDplus
Dihydroergotamine KEGG COMPOUND
Database Links Databases
888 DrugCentral
C00001724 KNApSAcK
C07798 KEGG COMPOUND
D07837 KEGG DRUG
DB00320 DrugBank
Dihydroergotamine Wikipedia
LSM-3619 LINCS
View more database links
Registry Numbers Types Sources
511-12-6 CAS Registry Number KEGG COMPOUND
511-12-6 CAS Registry Number ChemIDplus
511-12-6 CAS Registry Number NIST Chemistry WebBook
78887 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10954953 PubMed citation Europe PMC
20132337 PubMed citation Europe PMC
8145914 PubMed citation Europe PMC
Last Modified
22 February 2017