U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16N2O2
Molecular Weight 268.3104
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LYSERGIC ACID

SMILES

[H][C@@]12CC3=CNC4=C3C(=CC=C4)C1=C[C@H](CN2C)C(O)=O

InChI

InChIKey=ZAGRKAFMISFKIO-QMTHXVAHSA-N
InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization.
1995 Dec 27
Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan.
1996 Dec
Amnesic syndrome and severe ataxia following the recreational use of 3,4-methylene-dioxymethamphetamine (MDMA, 'ecstasy') and other substances.
2001
Ergot alkaloid transport across ruminant gastric tissues.
2001 Feb
Role of 5-HT(1A) and 5-HT(7) receptors in the facilitatory response induced by 8-OH-DPAT on learning consolidation.
2001 Jun
Lipid peroxidation product 4-hydroxy-2-nonenal acts synergistically with serotonin in inducing vascular smooth muscle cell proliferation.
2001 Mar
Lysophosphatidylcholine and reactive oxygen species mediate the synergistic effect of mildly oxidized LDL with serotonin on vascular smooth muscle cell proliferation.
2001 Mar 13
Hydrolysis of lysergamide to lysergic acid by Rhodococcus equi A4.
2001 Nov 17
Potent antagonism of 5-HT(3) and 5-HT(6) receptors by olanzapine.
2001 Nov 2
Modulation of neuroleptic activity of 9,10-didehydro-N-methyl-(2-propynyl)-6-methyl-8-aminomethylergoline bimaleinate (LEK-8829) by D1 intrinsic activity in hemi-parkinsonian rats.
2002 Feb
Case report: an ingestion of Hawaiian Baby Woodrose seeds associated with acute psychosis.
2003 Jun
Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro.
2005 Aug 18
Sequential aminodiene Diels-Alder approach to the ergoline skeleton.
2005 Aug 19
Structural analysis of a peptide synthetase gene required for ergopeptine production in the endophytic fungus Neotyphodium lolii.
2005 Oct
Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways.
2006 Apr
Detection of lysergic acid in ruminal fluid, urine, and in endophyte-infected tall fescue using high-performance liquid chromatography.
2006 Jul
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.
2007
Lysergic acid amide-induced posterior reversible encephalopathy syndrome with status epilepticus.
2008
Acute neuropsychological effects of MDMA and ethanol (co-)administration in healthy volunteers.
2008 Apr
Effects of selected combinations of tall fescue alkaloids on the vasoconstrictive capacity of fescue-naive bovine lateral saphenous veins.
2008 Apr
Mourning and melancholia revisited: correspondences between principles of Freudian metapsychology and empirical findings in neuropsychiatry.
2008 Jul 24
Indolealkylamines: biotransformations and potential drug-drug interactions.
2008 Jun
History of methysergide in migraine.
2008 Nov
Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group.
2008 Nov 20
Development and validation of an LC-MS method for quantitation of ergot alkaloids in lateral saphenous vein tissue.
2009 Aug 26
Bioaccumulation of ergovaline in bovine lateral saphenous veins in vitro.
2009 Jul
Methyl-ergometrine maleate from synchrotron powder diffraction data.
2009 Nov 28
Successful drug development despite adverse preclinical findings part 2: examples.
2010 Dec
Structural features for functional selectivity at serotonin receptors.
2013 May 3
Name Type Language
LYSERGIC ACID
MI  
Common Name English
(+)-LYSERGIC ACID
Common Name English
ERGOLINE-8-CARBOXYLIC ACID, 9,10-DIDEHYDRO-6-METHYL-, (8.BETA.)-
Common Name English
ERGOMETRINE MALEATE IMPURITY A [EP IMPURITY]
Common Name English
LYSERGIC ACID [MI]
Common Name English
(8.BETA.)-9,10-DIDEHYDRO-6-METHYLERGOLINE-8-CARBOXYLIC ACID
Systematic Name English
(8β)-6-methyl-9,10-didehydroergoline-8-carboxylic acid
Systematic Name English
Classification Tree Code System Code
DEA NO. 7300
Created by admin on Fri Dec 15 15:07:12 GMT 2023 , Edited by admin on Fri Dec 15 15:07:12 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID60904515
Created by admin on Fri Dec 15 15:07:12 GMT 2023 , Edited by admin on Fri Dec 15 15:07:12 GMT 2023
PRIMARY
MERCK INDEX
m6964
Created by admin on Fri Dec 15 15:07:12 GMT 2023 , Edited by admin on Fri Dec 15 15:07:12 GMT 2023
PRIMARY Merck Index
CHEBI
6604
Created by admin on Fri Dec 15 15:07:12 GMT 2023 , Edited by admin on Fri Dec 15 15:07:12 GMT 2023
PRIMARY
WIKIPEDIA
LYSERGIC ACID
Created by admin on Fri Dec 15 15:07:12 GMT 2023 , Edited by admin on Fri Dec 15 15:07:12 GMT 2023
PRIMARY
FDA UNII
ITO20DAO7J
Created by admin on Fri Dec 15 15:07:12 GMT 2023 , Edited by admin on Fri Dec 15 15:07:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-431-9
Created by admin on Fri Dec 15 15:07:12 GMT 2023 , Edited by admin on Fri Dec 15 15:07:12 GMT 2023
PRIMARY
CAS
82-58-6
Created by admin on Fri Dec 15 15:07:12 GMT 2023 , Edited by admin on Fri Dec 15 15:07:12 GMT 2023
PRIMARY
PUBCHEM
6717
Created by admin on Fri Dec 15 15:07:12 GMT 2023 , Edited by admin on Fri Dec 15 15:07:12 GMT 2023
PRIMARY