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Merck
CN

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

Key Documents

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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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B S Lee et al.
Bioorganic & medicinal chemistry letters, 10(14), 1559-1562 (2000-07-29)
6-Nitroquipazine has been known as one of the most potent and selective inhibitors of serotonin transporter in vitro and in vivo. Nine derivatives of 6-nitroquipazine were synthesized and tested for their potential abilities to displace [3H]citalopram binding to the rat
E Schlicker et al.
Naunyn-Schmiedeberg's archives of pharmacology, 342(5), 497-501 (1990-11-01)
Discs of pig retina were preincubated with 3H-noradrenaline, 3H-dopamine or 3H-serotonin and then superfused. Electrical field stimulation increased the outflow of tritium from discs preincubated with 3H-noradrenaline or 3H-dopamine, but no from discs preincubated with 3H-serotonin. The tritium content at
K Hashimoto et al.
European journal of pharmacology, 187(3), 295-302 (1990-10-23)
The characteristics of the binding [3H]6-nitroquipazine, a very potent and selective inhibitor of 5-hydroxytryptamine (5-HT; serotonin) uptake, to human platelet membranes were studied at a physiological temperature of 37 degrees C. The presence of a single saturable high-affinity binding component
Jae Hak Lee et al.
Bioorganic & medicinal chemistry, 15(10), 3499-3504 (2007-03-23)
Five C2'-substituted 6-nitroquipazine (6-NQ) derivatives were prepared and evaluated in terms of their biological abilities (K(i)) to displace [(3)H]citalopram binding to serotonin transporter. The relationship between their structure and biological activities revealed that shorter alkyl groups tend to possess higher
Byoung Se Lee et al.
Bioorganic & medicinal chemistry, 11(23), 4949-4958 (2003-11-08)
3-(3-[18F]Fluoropropyl)-6-nitroquipazine ([18F]FPNQ) as a 5-HT transporter imaging agents was designed, synthesized, and evaluated. FPNQ was selected due to its potent in vitro biological activity (K(i)=0.32 nM) in rat brain cortical membranes. The 18F-labeled FPNQ was prepared by reaction of the
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