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
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
Amnesic syndrome and severe ataxia following the recreational use of 3,4-methylene-dioxymethamphetamine (MDMA, 'ecstasy') and other substances.	2001	11744784
Biotechnology and genetics of ergot alkaloids.	2001 Dec	11778866
Lysophosphatidylcholine and reactive oxygen species mediate the synergistic effect of mildly oxidized LDL with serotonin on vascular smooth muscle cell proliferation.	2001 Mar 13	11245650
Hydrolysis of lysergamide to lysergic acid by Rhodococcus equi A4.	2001 Nov 17	11035188
Potent antagonism of 5-HT(3) and 5-HT(6) receptors by olanzapine.	2001 Nov 2	11711053
Lysergic acid diethylamide-induced Fos expression in rat brain: role of serotonin-2A receptors.	2002	12220572
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	11809861
Experiments towards the synthesis of the ergot alkaloids and related structures. Part 8. The total synthesis of 4-methyl-2,3,4,4a,5,6-hexahydrobenzo[f]quinoline-2-carbonitrile hydrochloride hemihydrate, an immediate precursor of the despyrrole analogues of lysergic acid and its amides.	2002 Jun	12443040
The ergot alkaloids. II. The degradation of ergotinine with alkali. Lysergic acid. 1934.	2002 Sep 20	12231659
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
Substance abuse on the college campus.	2005 Feb	15748936
Identification of the cytochrome P450 monooxygenase that bridges the clavine and ergoline alkaloid pathways.	2006 Apr	16538694
Structural basis for the spectral difference in luciferase bioluminescence.	2006 Mar 16	16541080
Chemical biology: a pocketful of colour.	2006 Mar 16	16541055
Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach.	2007	17465016
Physiological and digestive effects of Neotyphodium coenophialum-infected tall fescue fed to lambs.	2007 May	17296774
Indolealkylamines: biotransformations and potential drug-drug interactions.	2008 Jun	18454322
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
Bioaccumulation of ergovaline in bovine lateral saphenous veins in vitro.	2009 Jul	19286813
Experiences of drug use and ageing: health, quality of life, relationship and service implications.	2010 Sep	20626477

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

Download

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