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Safety Information

Q109

Sigma-Aldrich

6-Nitroquipazine maleate salt

solid

Synonym(s):

6-Nitro-2-(1-piperazinyl)quinoline maleate salt, Du 24565

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About This Item

Empirical Formula (Hill Notation):
C13H14N4O2 · C4H4O4
CAS Number:
77372-73-7
Molecular Weight:
374.35
MDL number:
MFCD00153868
UNSPSC Code:
12352202
PubChem Substance ID:
24278116
NACRES:
NA.77

form

solid

color

yellow

solubility

0.1 M HCl: 16 mg/mL
H2O: 5 mg/mL
methanol: 6 mg/mL
0.1 M NaOH: insoluble

storage temp.

2-8°C

SMILES string

[H]\C(=C(/[H])C(O)=O)C(O)=O.[O-][N+](=O)c1ccc2nc(ccc2c1)N3CCNCC3

InChI

1S/C13H14N4O2.C4H4O4/c18-17(19)11-2-3-12-10(9-11)1-4-13(15-12)16-7-5-14-6-8-16;5-3(6)1-2-4(7)8/h1-4,9,14H,5-8H2;1-2H,(H,5,6)(H,7,8)/b;2-1-

InChI key

LXOHMGALVZOYRF-BTJKTKAUSA-N

Gene Information

human ... HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , HTR3A(3359) , HTR3B(9177) , HTR3C(170572) , HTR3D(200909) , HTR3E(285242) , HTR4(3360) , HTR5A(3361) , HTR5B(645694) , HTR6(3362) , HTR7(3363)

Biochem/physiol Actions

Potent and selective serotonin transport blocker.

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
011M4708V
028H4639

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Mylène Karramkam et al.
Bioorganic & medicinal chemistry, 10(8), 2611-2623 (2002-06-12)
Considerable efforts have been engaged in the design, synthesis and pharmacological characterization of radioligands for imaging the serotonin transporter, based on its implication in several neuropsychiatric diseases, such as depression, anxiety and schizophrenia. In the 5-halo-6-nitroquipazine series, the fluoro derivative
Byoung Se Lee et al.
Bioorganic & medicinal chemistry letters, 12(5), 811-815 (2002-02-23)
Eleven 4-substituted derivatives of 6-nitroquipazine were synthesized and evaluated for their abilities to displace [3H]citalopram binding to the rat cortical synaptic membranes. Among them, 4-chloro-6-nitroquipazine was shown to possess the highest binding affinity (K(i=)0.03 nM) which was approximately 6 times
M Angeles Vicente-Torres et al.
Hearing research, 182(1-2), 43-47 (2003-09-02)
Cochlear serotonergic innervation is constituted by efferent fibers projecting both to the area below the inner and the outer hair cells. Previous detection of serotonin (5-HT) metabolites and 5-HT receptor mRNAs suggests the existence of serotonergic synaptic activity in the
K Fink et al.
European journal of pharmacology, 300(1-2), 79-82 (1996-04-04)
Guinea-pig cerebral cortical slices preincubated with [3H]5-hydroxytryptamine ([3H]5-HT) were superfused with Mg(2+)-free Krebs' solution. N-Methyl-D-aspartate (NMDA) stimulated tritium overflow in a concentration-dependent manner. The NMDA-evoked overflow was abolished by omission of CA2+ or presence of 1.2 mM Mg2+, but only
K Hashimoto et al.
The Journal of pharmacology and experimental therapeutics, 255(1), 146-153 (1990-10-01)
6-Nitroquipazine (DU 24565; 6-nitro 2-piperazinylquinoline) is a very potent 5-hydroxytryptamine (5-HT; serotonin) uptake inhibitor. It has been demonstrated very recently that [3H]-6-nitroquipazine is a suitable radioligand for studying 5-HT uptake sites. The present study evaluates [3H]6-nitroquipazine as a radioligand for
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