LYSERGIC ACID

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 Search

SMILES

CN1C[C@@H](C=C2[C@H]1CC3=CNC4=C3C2=CC=C4)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

Molecular Formula	C16H16N2O2
Molecular Weight	268.3104
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Structural features for functional selectivity at serotonin receptors.	2013-05-03	23519215
Successful drug development despite adverse preclinical findings part 2: examples.	2010-12	22272032
Experiences of drug use and ageing: health, quality of life, relationship and service implications.	2010-09	20626477
Determining the subjective effects of TFMPP in human males.	2010-08	20552171
Quantification of ergovaline using HPLC and mass spectrometry in Iranian Neotyphodium infected tall fescue.	2010-07	22049272
Chemical warfare agents.	2010-07	21829312
LSD but not lisuride disrupts prepulse inhibition in rats by activating the 5-HT(2A) receptor.	2010-02	19937319
Contractile response of fescue-naive bovine lateral saphenous veins to increasing concentrations of tall fescue alkaloids.	2010-01	19783700
Methyl-ergometrine maleate from synchrotron powder diffraction data.	2009-11-28	21578950
Self reported health status, and health service contact, of illicit drug users aged 50 and over: a qualitative interview study in Merseyside, United Kingdom.	2009-10-09	19818114
Development and validation of an LC-MS method for quantitation of ergot alkaloids in lateral saphenous vein tissue.	2009-08-26	19642695
Bioaccumulation of ergovaline in bovine lateral saphenous veins in vitro.	2009-07	19286813
Phylogenetic analyses reveal monophyletic origin of the ergot alkaloid gene dmaW in fungi.	2009-06-04	19812724
Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea.	2009-03-13	19139103
An overview of conventional and emerging analytical methods for the determination of mycotoxins.	2009-01	19333436
Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer.	2008-12	19330079
Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group.	2008-11-20	18956869
History of methysergide in migraine.	2008-11	18644039
The Frizzled 3 gene is associated with methamphetamine psychosis in the Japanese population.	2008-08-15	18702828
Mourning and melancholia revisited: correspondences between principles of Freudian metapsychology and empirical findings in neuropsychiatry.	2008-07-24	18652673
Indolealkylamines: biotransformations and potential drug-drug interactions.	2008-06	18454322
Acute neuropsychological effects of MDMA and ethanol (co-)administration in healthy volunteers.	2008-04	18305926
Effects of selected combinations of tall fescue alkaloids on the vasoconstrictive capacity of fescue-naive bovine lateral saphenous veins.	2008-04	18192563
The NARCONON drug education curriculum for high school students: a non-randomized, controlled prevention trial.	2008-03-19	18348735
Lysergic acid amide-induced posterior reversible encephalopathy syndrome with status epilepticus.	2008	18446448
Neurocognitive function in current and ex-users of ecstasy in comparison to both matched polydrug-using controls and drug-naïve controls.	2007-10	17605005
Physiological and digestive effects of Neotyphodium coenophialum-infected tall fescue fed to lambs.	2007-05	17296774
Nitrite inhalant use among young gay and bisexual men in Vancouver during a period of increasing HIV incidence.	2007-03-15	17362516
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.	2007	17465016
Assessment of vasoconstrictive potential of D-lysergic acid using an isolated bovine lateral saphenous vein bioassay.	2006-11	17032812
Effects of initial and extended exposure to an endophyte-infected tall fescue seed diet on faecal and urinary excretion of ergovaline and lysergic acid in mature geldings.	2006-08	16915339
Detection of lysergic acid in ruminal fluid, urine, and in endophyte-infected tall fescue using high-performance liquid chromatography.	2006-07	16921876
Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways.	2006-04	16538694
Structural basis for the spectral difference in luciferase bioluminescence.	2006-03-16	16541080
Chemical biology: a pocketful of colour.	2006-03-16	16541055
Ergot alkaloids--biology and molecular biology.	2006	17133714
The role of serendipity in drug discovery.	2006	17117615
Mass spectral characterization of ergot alkaloids by electrospray ionization, hydrogen/deuterium exchange, and multiple stage mass spectrometry: Usefulness of precursor ion scan experiments.	2006	16941545
Dextromethorphan abuse in Thai adolescents: A report of two cases and review of literature.	2005-11	16856446
Electrospray[+] tandem quadrupole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds.	2005-11	16278935
Structural analysis of a peptide synthetase gene required for ergopeptine production in the endophytic fungus Neotyphodium lolii.	2005-10	16243728
Sequential aminodiene Diels-Alder approach to the ergoline skeleton.	2005-08-19	16095303
Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro.	2005-08-18	15921820
Substance abuse on the college campus.	2005-02	15748936
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.	2004-11	15470699
Enantioefficient synthesis of alpha-ergocryptine: first direct synthesis of (+)-lysergic acid.	2004-09-03	15373483
The dopamine D1 receptor agonist and D2 receptor antagonist LEK-8829 attenuates reinstatement of cocaine-seeking in rats.	2004-06	15138661
A new synthesis of lysergic acid.	2004-01-08	14703336
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.	1996-12	8967979
Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization.	1995-12-27	8549774

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:47:06 GMT 2025` Edited by `admin` on `Mon Mar 31 17:47:06 GMT 2025`
Record UNII	ITO20DAO7J
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

(+)-LYSERGIC ACID

Preferred 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

(8?)-6-methyl-9,10-didehydroergoline-8-carboxylic acid

Systematic Name

English

Classification Tree Code System Code

DEA NO.

7300