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

[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

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
Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization.	1995 Dec 27	8549774
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	8967979
A new synthesis of lysergic acid.	2004 Jan 8	14703336
The dopamine D1 receptor agonist and D2 receptor antagonist LEK-8829 attenuates reinstatement of cocaine-seeking in rats.	2004 Jun	15138661
Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.	2004 Nov	15470699
Enantioefficient synthesis of alpha-ergocryptine: first direct synthesis of (+)-lysergic acid.	2004 Sep 3	15373483
Valerian extract and valerenic acid are partial agonists of the 5-HT5a receptor in vitro.	2005 Aug 18	15921820
Sequential aminodiene Diels-Alder approach to the ergoline skeleton.	2005 Aug 19	16095303
Substance abuse on the college campus.	2005 Feb	15748936
Dextromethorphan abuse in Thai adolescents: A report of two cases and review of literature.	2005 Nov	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 Nov	16278935
Structural analysis of a peptide synthetase gene required for ergopeptine production in the endophytic fungus Neotyphodium lolii.	2005 Oct	16243728
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
Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways.	2006 Apr	16538694
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 Aug	16915339
Detection of lysergic acid in ruminal fluid, urine, and in endophyte-infected tall fescue using high-performance liquid chromatography.	2006 Jul	16921876
Structural basis for the spectral difference in luciferase bioluminescence.	2006 Mar 16	16541080
Chemical biology: a pocketful of colour.	2006 Mar 16	16541055
Assessment of vasoconstrictive potential of D-lysergic acid using an isolated bovine lateral saphenous vein bioassay.	2006 Nov	17032812
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.	2007	17465016
Nitrite inhalant use among young gay and bisexual men in Vancouver during a period of increasing HIV incidence.	2007 Mar 15	17362516
Physiological and digestive effects of Neotyphodium coenophialum-infected tall fescue fed to lambs.	2007 May	17296774
Neurocognitive function in current and ex-users of ecstasy in comparison to both matched polydrug-using controls and drug-naïve controls.	2007 Oct	17605005
Lysergic acid amide-induced posterior reversible encephalopathy syndrome with status epilepticus.	2008	18446448
Acute neuropsychological effects of MDMA and ethanol (co-)administration in healthy volunteers.	2008 Apr	18305926
Effects of selected combinations of tall fescue alkaloids on the vasoconstrictive capacity of fescue-naive bovine lateral saphenous veins.	2008 Apr	18192563
The Frizzled 3 gene is associated with methamphetamine psychosis in the Japanese population.	2008 Aug 15	18702828
Recognition properties and competitive assays of a dual dopamine/serotonin selective molecularly imprinted polymer.	2008 Dec	19330079
Mourning and melancholia revisited: correspondences between principles of Freudian metapsychology and empirical findings in neuropsychiatry.	2008 Jul 24	18652673
Indolealkylamines: biotransformations and potential drug-drug interactions.	2008 Jun	18454322
The NARCONON drug education curriculum for high school students: a non-randomized, controlled prevention trial.	2008 Mar 19	18348735
History of methysergide in migraine.	2008 Nov	18644039
Total synthesis of (+/-)-lysergic acid, lysergol, and isolysergol by palladium-catalyzed domino cyclization of amino allenes bearing a bromoindolyl group.	2008 Nov 20	18956869
Development and validation of an LC-MS method for quantitation of ergot alkaloids in lateral saphenous vein tissue.	2009 Aug 26	19642695
An overview of conventional and emerging analytical methods for the determination of mycotoxins.	2009 Jan	19333436
Bioaccumulation of ergovaline in bovine lateral saphenous veins in vitro.	2009 Jul	19286813
Phylogenetic analyses reveal monophyletic origin of the ergot alkaloid gene dmaW in fungi.	2009 Jun 4	19812724
Combinatorial assembly of simple and complex D-lysergic acid alkaloid peptide classes in the ergot fungus Claviceps purpurea.	2009 Mar 13	19139103
Methyl-ergometrine maleate from synchrotron powder diffraction data.	2009 Nov 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 Oct 9	19818114
Determining the subjective effects of TFMPP in human males.	2010 Aug	20552171
Successful drug development despite adverse preclinical findings part 2: examples.	2010 Dec	22272032
LSD but not lisuride disrupts prepulse inhibition in rats by activating the 5-HT(2A) receptor.	2010 Feb	19937319
Contractile response of fescue-naive bovine lateral saphenous veins to increasing concentrations of tall fescue alkaloids.	2010 Jan	19783700
Quantification of ergovaline using HPLC and mass spectrometry in Iranian Neotyphodium infected tall fescue.	2010 Jul	22049272
Chemical warfare agents.	2010 Jul	21829312
Experiences of drug use and ageing: health, quality of life, relationship and service implications.	2010 Sep	20626477
Structural features for functional selectivity at serotonin receptors.	2013 May 3	23519215

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:07:12 UTC 2023` Edited by `admin` on `Fri Dec 15 15:07:12 UTC 2023`
Record UNII	ITO20DAO7J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LYSERGIC ACID

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