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6-Anilinoquinoline-5,8-quinone

Name: 6-Anilinoquinoline-5,8-quinone
Brand: SIGMA

≥95% (TLC), solid

Synonym(s):

6-(Phenylamino)-5,8-quinolinedione, LY-83,583, LY83583

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₁₀N₂O₂

CAS Number:

91300-60-6

Molecular Weight:

250.25

NACRES:

NA.77

PubChem Substance ID:

24891108

UNSPSC Code:

41106305

MDL number:

MFCD00210756

Assay:

≥95% (TLC)

Form:

solid

Quality level:

200

Pricing and availability is not currently available.

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Properties

Quality Level

200

assay

≥95% (TLC)

form

solid

color

violet

solubility

0.1 M HCl: 1 mg/mL, methanol: 11 mg/mL, ethanol: 8 mg/mL

storage temp.

2-8°C

SMILES string

O=C1C=C(Nc2ccccc2)C(=O)c3cccnc13

InChI

1S/C15H10N2O2/c18-13-9-12(17-10-5-2-1-3-6-10)15(19)11-7-4-8-16-14(11)13/h1-9,17H

InChI key

GXIJYWUWLNHKNW-UHFFFAOYSA-N

Description

Application

6-Anilinoquinoline-5,8-quinone inhibits soluble guanylate cyclase and cGMP production. 6-Anilinoquinoline-5,8-quinone also blocks the release of intracellular Ca²⁺ and antigen-induced leukotrienes.

Biochem/physiol Actions

Blocks cGMP production; inhibits intracellular Ca²⁺ release; blocks the effects of nitric oxide. Inhibits antigen-induced leukotriene release.

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This Item	N7537	SML1856	D3943
Sigma-Aldrich A6563 6-Anilinoquinoline-5,8-quinone	Sigma-Aldrich N7537 NSC 663284	Sigma-Aldrich SML1856 8-Aminoguanine	Sigma-Aldrich D3943 DAPH
form solid	form solid	form powder	form solid
assay ≥95% (TLC)	assay ≥98% (HPLC)	assay ≥95% (HPLC)	assay ≥98% (HPLC)
Quality Level 200	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility 0.1 M HCl: 1 mg/mL, ethanol: 8 mg/mL, methanol: 11 mg/mL	solubility DMSO: ≥10 mg/mL, H₂O: insoluble	solubility 0.1 M NaOH: 2 mg/mL, clear (warmed)	solubility DMSO: >20 mg/mL, H₂O: insoluble
color violet	color red	color white to beige	color orange

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Evidence that an L-arginine/nitric oxide dependent elevation of tissue cyclic GMP content is involved in depression of vascular reactivity by endotoxin.

I Fleming et al.

British journal of pharmacology, 103(1), 1047-1052 (1991-05-01)

1. The aim of this investigation was to study the relationship between contractile responsiveness, activation of the L-arginine pathway and tissue levels of guanosine 3':5'cyclic monophosphate (cylic GMP) in aortic rings removed from rats 4 h after intraperitoneal administration of

ATP and NO dually control migration of microglia to nerve lesions.

Yuanli Duan et al.

Developmental neurobiology, 69(1), 60-72 (2008-11-26)

Microglia migrate rapidly to lesions in the central nervous system (CNS), presumably in response to chemoattractants including ATP released directly or indirectly by the injury. Previous work on the leech has shown that nitric oxide (NO), generated at the lesion

In vivo and in vitro studies of a putative inhibitor of cyclic guanosine 3',5'-monophosphate production.

M A Brandt et al.

Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 196(1), 30-35 (1991-01-01)

Our main objective was to test the efficacy of 6-anilino-5,8-quinolinedione (LY83583) in vivo, a putative inhibitor of cyclic guanosine 3',5'-monophosphate (cGMP) production. If the drug proved capable of lowering plasma, vascular, and kidney levels of cGMP and of inhibiting the

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Global Trade Item Number

SKU	GTIN
A6563-5MG	04061832895642

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