lysergic acid diethylamide (CHEBI:6605)

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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

Average Mass

323.43200

Monoisotopic Mass

323.19976

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.

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)

Incoming	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	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

Last Modified

22 February 2017

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.