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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 Classen et al.
Naunyn-Schmiedeberg's archives of pharmacology, 326(3), 198-202 (1984-06-01)
Rat brain cortex slices were prepared in order to study the influence of DU 24565 (6-nitroquipazine) and quipazine on the accumulation of tritium, and to investigate the effects of DU 24565 on the electrically evoked (3 Hz) tritium overflow from
M Okada et al.
The European journal of neuroscience, 11(1), 1-9 (1999-02-13)
To clarify the effects of adenosine receptor subtypes (A1, A2 and A3) on hippocampal serotonin (5-HT) release and 5-HT reuptake activity, hippocampal extracellular 5-HT levels were determined in vivo by microdialysis in freely moving rats. Selective 5-HT reuptake inhibitor (SSRI)
S Rutz et al.
Neuroscience, 146(2), 643-658 (2007-03-27)
5-HT released from serotonergic axon terminals in the septal nuclei modulates the activity of septal output neurons (e.g. septohippocampal cholinergic neurons) bearing somatodendritic 5-HT receptors. Therefore, we studied the mechanisms involved in the presynaptic modulation of 5-HT release in the
Byung Seok Moon et al.
Bioorganic & medicinal chemistry, 13(16), 4952-4959 (2005-07-05)
On the basis of the structure-activity relationship (SAR) of 4-chloro-6-nitroquipazine (Ki = 0.03 nM) and 3-fluoropropyl-6-nitroquipazine (Ki = 0.32 nM), 3-alkyl-4-halo-6-nitroquipazines were synthesized and tested for their potential abilities in vitro to displace [3H]citalopram binding to the rat cortical membranes.
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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