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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

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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
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
K Hashimoto et al.
European journal of pharmacology, 180(2-3), 273-281 (1990-05-16)
6-Nitroquipazine is a very potent and selective inhibitor of neuronal 5-hydroxytryptamine (5-HT; serotonin) uptake. We have characterized the specific binding of [3H]6-nitroquipazine to rat brain membranes at 22 degrees C. The present results indicate the presence of a single saturable
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
L Descarries et al.
Synapse (New York, N.Y.), 21(2), 131-139 (1995-10-01)
Direct counting of axon terminals (varicosities) labeled by uptake/storage of a tritiated monoamine provides a means to test radioligands of the corresponding membrane transporter as quantitative markers of regional monoamine innervation density in brain tissue. In autoradiographs from alternate rat
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