CHEBI:6605 - lysergic acid diethylamide

ChEBI IDCHEBI:6605
ChEBI Namelysergic acid diethylamide
Stars
DefinitionAn ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.
Last Modified22 February 2017
DownloadsMolfile
FormulaC20H25N3O
Net Charge0
Average Mass323.440
Monoisotopic Mass323.19976
SMILES[H][C@@]12Cc3cnc4cccc(c34)C1=C[C@@H](C(=O)N(CC)CC)CN2C
InChIInChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1
InChIKeyVAYOSLLFUXYJDT-RDTXWAMCSA-N
Wikipedia
Roles Classification
Biological Roles:
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.
dopamine agonist  A drug that binds to and activates dopamine receptors.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
hallucinogen  Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.
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.
dopamine agonist  A drug that binds to and activates dopamine receptors.
ChEBI Ontology
Outgoing Relation(s)
lysergic acid diethylamide (CHEBI:6605) has functional parent lysergamide (CHEBI:4819)
lysergic acid diethylamide (CHEBI:6605) has role dopamine agonist (CHEBI:51065)
lysergic acid diethylamide (CHEBI:6605) has role hallucinogen (CHEBI:35499)
lysergic acid diethylamide (CHEBI:6605) has role serotonergic agonist (CHEBI:35941)
lysergic acid diethylamide (CHEBI:6605) is a ergoline alkaloid (CHEBI:60529)
lysergic acid diethylamide (CHEBI:6605) is a monocarboxylic acid amide (CHEBI:29347)
lysergic acid diethylamide (CHEBI:6605) is a organic heterotetracyclic compound (CHEBI:38163)
Incoming Relation(s)
LSD-d3 (CHEBI:194178) has functional parent lysergic acid diethylamide (CHEBI:6605)
IUPAC Name 
(8R)-9,10-didehydro-N,N-diethyl-6-methylergoline-8-carboxamide
Synonyms  Source
N,N-diethyl-(+)-lysergamideNIST Chemistry WebBook
N,N-diethyllysergamideNIST Chemistry WebBook
N,N-diethyl-D-lysergamideChemIDplus
(+)-LSDNIST Chemistry WebBook
LSDKEGG COMPOUND
LSD 25NIST Chemistry WebBook
Manual XrefsDatabases
1621DrugCentral
C07542KEGG COMPOUND
CPD-14458MetaCyc
Lysergic_acid_diethylamideWikipedia
US2736728Patent
US2774763Patent
US3141887Patent
Registry NumbersSources
Reaxys:94179Reaxys
CAS:50-37-3KEGG COMPOUND
CAS:50-37-3NIST Chemistry WebBook
CAS:50-37-3ChemIDplus
Citations