QUINOLINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H7N
Molecular Weight	129.1586
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C1=CC2=CC=CN=C2C=C1

InChI

InChIKey=SMWDFEZZVXVKRB-UHFFFAOYSA-N

InChI=1S/C9H7N/c1-2-6-9-8(4-1)5-3-7-10-9/h1-7H

HIDE SMILES / InChI

Molecular Formula	C9H7N
Molecular Weight	129.1586
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26507702 | https://www.epa.gov/sites/production/files/2016-09/documents/quinoline.pdf

Quinoline, an alkaloid from various plant species, is a flavouring ingredient. It’s used mainly as an intermediate in the manufacture of other products. Quinoline is considered as one of the most toxic and carcinogenic compounds and is commonly found in industrial wastewaters, which require treatment before being discharged.

Approval Year

PubMed

Title	Date	PubMed
Inhibitory analogs of ubiquinol act anti-cooperatively on the Yeast cytochrome bc1 complex. Evidence for an alternating, half-of-the-sites mechanism of ubiquinol oxidation.	2002-01-11	11700316
Iron(III) spin-crossover compounds with a wide apparent thermal hysteresis around room temperature.	2001-11-28	11716720
Identification of the alkaloids of Galipea officinalis by gas chromatography-mass spectrometry.	2001-11-14	11705258
Cyclometalated complexes of Ru(II) with 2-aryl derivatives of quinoline and 1,10-phenanthroline.	2001-11-05	11681896
Isolation of mitochondria from Plasmodium falciparum showing dihydroorotate dependent respiration.	2001-11	11719114
Texture analysis of fluorescence lifetime images of AT- and GC-rich regions in nuclei.	2001-11	11668197
Synthesis of some new quinoline derivatives: new routes to synthesize polysubstituted 2(1H)-quinolone derivatives.	2001-10-30	11680080
The electric field generated by photosynthetic reaction center induces rapid reversed electron transfer in the bc1 complex.	2001-10-23	11601982
Quinoline, quinazoline and acridone alkaloids.	2001-10	11699885
Direct measurement of conformational changes on DNA molecule intercalating with a fluorescence dye in an electrophoretic buffer solution by means of atomic force microscopy.	2001-10	11669510
In vitro effect of alkaloids on bloodstream forms of Trypanosoma brucei and T. congolense.	2001-10	11582539
Interactions of the antimalarial drug mefloquine with the human cardiac potassium channels KvLQT1/minK and HERG.	2001-10	11561091
Characterization of three bioenergetically active respiratory terminal oxidases in the cyanobacterium Synechocystis sp. strain PCC 6803.	2001-09-25	11583851
Catalytic protein film voltammetry from a respiratory nitrate reductase provides evidence for complex electrochemical modulation of enzyme activity.	2001-09-25	11560477
Coordinatively unsaturated W(IV)-bis(pyridine) complexes, a reactive source of W(IV).	2001-09-24	11559063
Modulation of human mammary cell sensitivity to paclitaxel by new quinoline sulfonamides.	2001-09-17	11549446
Role of endocytosis in the transfection of L929 fibroblasts by polyethylenimine/DNA complexes.	2001-09-03	11513802
SK3 is an important component of K(+) channels mediating the afterhyperpolarization in cultured rat SCG neurones.	2001-09-01	11533126
Structural assignment of isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione mono- and disulfonic acids by liquid chromatography electrospray and atmospheric pressure chemical ionization tandem mass spectrometry.	2001-09	11599080
Quinoline alkaloids and other constituents of Melicope semecarpifolia with antiplatelet aggregation activity.	2001-09	11575945
Synthesis and fungicidal activity of a series of novel aryloxylepidines.	2001-09	11561412
Insights from the structure of the yeast cytochrome bc1 complex: crystallization of membrane proteins with antibody fragments.	2001-08-31	11532444
Synthesis and characterization of non-steroidal ligands for the glucocorticoid receptor: selective quinoline derivatives with prednisolone-equivalent functional activity.	2001-08-30	11520196
Photobleaching of asymmetric cyanines used for fluorescence imaging of single DNA molecules.	2001-08-22	11506554
Intercalating fluorescence dye YOYO-1 prevents the folding transition in giant duplex DNA.	2001-08-17	11500031
Primary kinetic isotope effects on hydride transfer from 1,3-dimethyl-2-phenylbenzimidazoline to NAD(+) analogues.	2001-08-08	11480968
Diffusion coefficient of DNA molecules during free solution electrophoresis.	2001-08	11519946
"One-pot" synthesis and antimalarial activity of formamidine derivatives of 4-anilinoquinoline.	2001-08	11515580
Biodegradation of quinoline by gel immobilized Burkholderia sp.	2001-08	11513389
Site-directed mutation of the highly conserved region near the Q-loop of the cytochrome bd quinol oxidase from Escherichia coli specifically perturbs heme b595.	2001-07-24	11456494
1,3-Biarylureas as selective non-peptide antagonists of the orexin-1 receptor.	2001-07-23	11459658
Preparative separation of isomeric 2-(2-quinolinyl)-1H-indene-1,3(2H)-dione monosulfonic acids of the color additive D&C Yellow No. 10 (quinoline yellow) by pH-zone-refining counter-current chromatography.	2001-07-20	11510564
Catalytic enantioselective Reissert-type reaction: development and application to the synthesis of a potent NMDA receptor antagonist (-)-L-689,560 using a solid-supported catalyst.	2001-07-18	11448184
Oxazole yellow homodimer YOYO-1-labeled DNA: a fluorescent complex that can be used to assess structural changes in DNA following formation and cellular delivery of cationic lipid DNA complexes.	2001-07-02	11420144
A new quinoline derivative MS-209 reverses multidrug resistance and inhibits multiorgan metastases by P-glycoprotein-expressing human small cell lung cancer cells.	2001-07	11473730
Stereochemistry of new nitrogen containing heterocyclic aldehyde. VI. Novel structural and properties models of uranyl with quinoline azodyes.	2001-07	11471721
Hydrogen bonding and dipolar interactions between quinolines and organic solvents. Nuclear magnetic resonance and ultraviolet-visible spectroscopic studies.	2001-07	11471706
A novel quinoline alkaloid possessing a 7-benzyl group from the centipede, Scolopendra subspinipes.	2001-07	11456108
Phototoxicity of azaarene isomers to the marine flagellate Dunaliella tertiolecta.	2001-07	11434296
Modification of voltage-dependent gating of potassium channels by free form of tryptophan side chain.	2001-07	11423398
Enhancing reductive cleavage of aromatic carboxamides.	2001-06-28	11418039
First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Alder reaction using chiral Ti(IV) complex.	2001-06-28	11418027
Comparison of chromatographic properties of cyanopropyl-, diol- and aminopropyl- polar-bonded stationary phases by the retention of model compounds in normal-phase liquid chromatography systems.	2001-06-01	11459310
Probing the ubiquinone reduction site in bovine mitochondrial complex I using a series of synthetic ubiquinones and inhibitors.	2001-06	11695832
Comparison of pharmacophore cinnoline and quinoline systems on the basis of computer calculation and pharmacological screening of their condensed systems.	2001-06	11446173
A new type-II NADH dehydrogenase from the archaeon Acidianus ambivalens: characterization and in vitro reconstitution of the respiratory chain.	2001-02	11460922
An old but simple and efficient method to elucidate the oxidation mechanism of NAD(P)H model 1-Aryl-1,4-dihydronicotinamides by cations 2-methyl-5-nitroisoquinolium, tropylium, and xanthylium in aqueous solution.	2001-01-26	11429802
Ribosomes in the squid giant axon.	2001	11719007
Crystal and molecular structure of a new cobalt complex of quinine.	2001	11693482
Nitrate reduction in the periplasm of gram-negative bacteria.	2001	11450112

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:53:25 GMT 2025` Edited by `admin` on `Mon Mar 31 18:53:25 GMT 2025`
Record UNII	E66400VT9R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUINOLINE

Systematic Name

English

FEMA NO. 3470

Preferred Name

English

QUINOLINE [HSDB]

Common Name

English

NSC-3396

Code

English

LEUKOL

Common Name

English

CHINOLEINE

Common Name

English

LEUCOL

Common Name

English

QUINOLINE [FHFI]

Common Name

English

2,3-BENZOPYRIDINE

Common Name

English

1-AZANAPHTHALENE

Systematic Name

English

1-BENZAZINE

Common Name

English

BENZO(B)PYRIDINE

Systematic Name

English

QUINOLINE [MI]

Common Name

English

QUINOLINE [IARC]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

468714