6-Nitroquipazine

6-Nitroquipazine
Clinical data
ATC code	none;
Legal status
Legal status	In general: uncontrolled;
Identifiers
	IUPAC name 6-nitro-2-piperazin-1-yl-quinoline;
CAS Number	77372-73-7 ;
PubChem CID	5012;
ChemSpider	4837 ;
UNII	28M0X094BH;
ChEMBL	ChEMBL41140 ;
CompTox Dashboard (EPA)	DTXSID7044001 ;
Chemical and physical data
Formula	C13H14N4O2
Molar mass	258.281 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [O-][N+](=O)c3cc1c(nc(cc1)N2CCNCC2)cc3;
	InChI InChI=1S/C13H14N4O2/c18-17(19)11-2-3-12-10(9-11)1-4-13(15-12)16-7-5-14-6-8-16/h1-4,9,14H,5-8H2 ; Key:GGDBEAVVGFNWIA-UHFFFAOYSA-N ;
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6-Nitroquipazine (developmental code name DU-24,565) is a potent and selective serotonin reuptake inhibitor used in scientific research.^[1]^[2]

6-Nitroquipazine has been found to inhibit melanogenesis in-vitro,^[3] suggesting that it can be used for skin whitening.

References

^ Vaatstra WJ, Deiman-Van Aalst WM, Eigeman L (March 1981). "Du 24565, a quipazine derivative, a potent selective serotonin uptake inhibitor". European Journal of Pharmacology. 70 (2): 195–202. doi:10.1016/0014-2999(81)90214-4. PMID 6973481.
^ Classen K, Göthert M, Schlicker E (June 1984). "Effects of DU 24565 (6-nitroquipazine) on serotoninergic and noradrenergic neurones of the rat brain and comparison with the effects of quipazine". Naunyn-Schmiedeberg's Archives of Pharmacology. 326 (3): 198–202. doi:10.1007/bf00505318. PMID 6206407. S2CID 20858707.
^ McEwan M, Parsons PG (July 1987). "Inhibition of melanization in human melanoma cells by a serotonin uptake inhibitor". The Journal of Investigative Dermatology. 89 (1): 82–86. doi:10.1111/1523-1747.ep12580425. PMID 3110297. No-cost access but non-free license.

[pmid6973481-1] Vaatstra WJ, Deiman-Van Aalst WM, Eigeman L (March 1981). "Du 24565, a quipazine derivative, a potent selective serotonin uptake inhibitor". European Journal of Pharmacology. 70 (2): 195–202. doi:10.1016/0014-2999(81)90214-4. PMID 6973481.

[pmid6206407-2] Classen K, Göthert M, Schlicker E (June 1984). "Effects of DU 24565 (6-nitroquipazine) on serotoninergic and noradrenergic neurones of the rat brain and comparison with the effects of quipazine". Naunyn-Schmiedeberg's Archives of Pharmacology. 326 (3): 198–202. doi:10.1007/bf00505318. PMID 6206407. S2CID 20858707.

[3] McEwan M, Parsons PG (July 1987). "Inhibition of melanization in human melanoma cells by a serotonin uptake inhibitor". The Journal of Investigative Dermatology. 89 (1): 82–86. doi:10.1111/1523-1747.ep12580425. PMID 3110297. No-cost access but non-free license.

[1]

[2]

[3]

v t e Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	2C-B-PP 3,4-CFP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

Clinical data

ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name 6-nitro-2-piperazin-1-yl-quinoline
CAS Number	77372-73-7^N
PubChem CID	5012
ChemSpider	4837^Y
UNII	28M0X094BH
ChEMBL	ChEMBL41140^Y
CompTox Dashboard (EPA)	DTXSID7044001
Chemical and physical data
Formula	C₁₃H₁₄N₄O₂
Molar mass	258.281 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [O-][N+](=O)c3cc1c(nc(cc1)N2CCNCC2)cc3
InChI InChI=1S/C13H14N4O2/c18-17(19)11-2-3-12-10(9-11)1-4-13(15-12)16-7-5-14-6-8-16/h1-4,9,14H,5-8H2^Y Key:GGDBEAVVGFNWIA-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

6-Nitroquipazine

See also

References

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