CHEBI:6605 - lysergic acid diethylamide

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ChEBI Name lysergic acid diethylamide
ChEBI ID CHEBI:6605
Definition An ergoline alkaloid arising from formal condensation of lysergic acid with diethylamine.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H25N3O
Net Charge 0
Average Mass 323.43200
InChI InChI=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
InChIKey VAYOSLLFUXYJDT-RDTXWAMCSA-N
SMILES [H][C@@]12Cc3c[nH]c4cccc(C1=C[C@H](CN2C)C(=O)N(CC)CC)c34
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.
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.
(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.
dopamine agonist
A drug that binds to and activates dopamine receptors.
hallucinogen
Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations and other alterations of mood and thinking.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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)
IUPAC Name
(8R)-9,10-didehydro-N,N-diethyl-6-methylergoline-8-carboxamide
Synonyms Sources
(+)-LSD NIST Chemistry WebBook
D-lysergic acid diethylamide ChemIDplus
LSD KEGG COMPOUND
LSD 25 NIST Chemistry WebBook
Lysergic acid diethylamide KEGG COMPOUND
Lysergide KEGG COMPOUND
Lysergsäurediäthylamid ChEBI
Lysergsäurediethylamid ChEBI
N,N-diethyl-(+)-lysergamide NIST Chemistry WebBook
N,N-diethyl-D-lysergamide ChemIDplus
N,N-diethyllysergamide NIST Chemistry WebBook
Database Links Databases
C07542 KEGG COMPOUND
CPD-14458 MetaCyc
Lysergic_acid_diethylamide Wikipedia
US2736728 Patent
US2774763 Patent
US3141887 Patent
View more database links
Registry Numbers Types Sources
50-37-3 CAS Registry Number KEGG COMPOUND
50-37-3 CAS Registry Number ChemIDplus
50-37-3 CAS Registry Number NIST Chemistry WebBook
94179 Reaxys Registry Number Reaxys
94179 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11723224 PubMed citation CiteXplore
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8428600 PubMed citation CiteXplore
9698051 PubMed citation CiteXplore
Last Modified
28 July 2014
General Comment
2011-02-15 A semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an altered sense of time and spiritual experiences. It is used mainly as an entheogen, recreational drug, and as an agent in psychedelic therapy.