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Sigma-Aldrich

8-Aminoquinoline

98%

Synonym(s):

8-Quinolinamine

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About This Item

Empirical Formula (Hill Notation):
C9H8N2
CAS Number:
578-66-5
Molecular Weight:
144.17
Beilstein:
114474
EC Number:
209-427-9
MDL number:
MFCD00006809
UNSPSC Code:
12352100
PubChem Substance ID:
24855768
NACRES:
NA.22

Assay

98%

form

solid

reaction suitability

reaction type: C-H Activation
reagent type: catalyst

bp

174 °C/26 mmHg (lit.)

mp

60-65 °C (lit.)

SMILES string

Nc1cccc2cccnc12

InChI

1S/C9H8N2/c10-8-5-1-3-7-4-2-6-11-9(7)8/h1-6H,10H2

InChI key

WREVVZMUNPAPOV-UHFFFAOYSA-N

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General description

8-Aminoquinoline fluoresce moderately to weakly in low dielectric media but not in strongly hydrogen-bonding or acidic aqueous media. The reaction of 8-aminoquinoline with chromium (III), manganese (II), iron (II) and (III), cobalt (II), nickel (II), copper (II), zinc (II), cadmium (II) and platinum (II) salts has been studied.

Application

8-Aminoquinoline has been used in:
  • preparation of base-stabilized terminal borylene complex of osmium
  • spectrophotometric determination of bivalent palladium

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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José M Pérez-Victoria et al.
Antimicrobial agents and chemotherapy, 55(8), 3838-3844 (2011-06-08)
Although oral miltefosine represented an important therapeutic advance in the treatment of leishmaniasis, the appearance of resistance remains a serious threat. LMDR1/LABCB4, a P-glycoprotein-like transporter included in the Leishmania ABC (ATP-binding cassette) family, was the first molecule shown to be
Sílvia Vale-Costa et al.
Antimicrobial agents and chemotherapy, 56(11), 5774-5781 (2012-08-29)
The current treatment of visceral leishmaniasis is made difficult by the low efficacy, elevated costs, low bioavailability, and high toxicity of many of the available drugs. Primaquine, an antimalarial 8-aminoquinoline, displays activity against Leishmania spp., and several of its derivatives
Luis Carvalho et al.
Antimicrobial agents and chemotherapy, 55(9), 4204-4210 (2011-06-15)
The 8-aminoquinoline analogue sitamaquine (SQ) is an oral antileishmanial drug currently undergoing phase 2b clinical trials for the treatment of visceral leishmaniasis. In the present study, we investigated the mechanism of action of this drug in Leishmania donovani promastigotes. SQ
Some transition metal complexes of 8-aminoquinoline.
Fanning JC and Taylor LT.
J. Inorg. Nucl. Chem., 27(10), 2217-2223 (1965)
Hla Y Myint et al.
The American journal of tropical medicine and hygiene, 85(6), 1010-1014 (2011-12-07)
Because 8-aminoquinolines affect critical survival stages of Plasmodium parasites, treatment and control of malaria could be markedly improved by more widespread use of these drugs; however, hemolytic toxicity, which is widely prevalent in G6PD-deficient patients, severely constrains this use. Primaquine
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