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About This Item
Empirical Formula (Hill Notation):
C13H14N4O2 · C4H4O4
CAS Number:
Molecular Weight:
374.35
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352202
MDL number:
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-
SMILES string
[H]\C(=C(/[H])C(O)=O)C(O)=O.[O-][N+](=O)c1ccc2nc(ccc2c1)N3CCNCC3
InChI key
LXOHMGALVZOYRF-BTJKTKAUSA-N
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
Gene Information
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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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
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
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
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
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