Quipazine

Names

[ Name ]:
Quipazine

[Synonym ]:
Quinoline, 2-(1-piperazinyl)-
2-(piperazin-1-yl)quinoline
Quipazine
MFCD00242605
2-(1-Piperazinyl)quinoline
2-piperazin-1-yl-quinoline

Biological Activity

[Description]:

Quipazine is a 5-HT agonist with a Ki value of 1.4 nM for displaces [3H]GR65630 from 5-HT3R in rat. Quipazine shows antiviral activity against SARS-CoV-2 with an EC50 of 31.64 μM. Quipazine behaves as a 5-HT3R agonist in peripheral models. Quipazine can be used for neurological disease research[1][2][3][4].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> SARS-CoV

Research Areas >> Neurological Disease

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

[In Vitro]

Quipazine 对 5-HT1 和 5-HT2 具有结合效能，Ki 值均为 230 nM[3]。 Quipazine 取代大鼠内皮层中 5-HT3R 的 [3H]GR65630，Ki 值为 1.4 nM[3]。 Quipazine 对大鼠迷走神经具有拮抗作用，对 5-HT2，5-HT1 以及抑制 5-HT 释放的 pIC50 值分别为 6.1，6.49 和 6.17[4]。

[In Vivo]

Quipazine (2.5，5 和 7.5 mg/kg，每个剂量各一次；腹腔注射) 影响雄性和雌性大鼠对不同宏量营养素饮食的膳食自我选择[1]。

[References]

[1]. Mok E, et al. Effect of quipazine, a selective 5-HT3 agonist, on dietary self-selection of different macronutrient diets in male and female rats. Appetite. 2000 Jun;34(3):313-25.

[2]. Günther S, et al. X-ray screening identifies active site and allosteric inhibitors of SARS-CoV-2 main protease. Science. 2021 May 7;372(6542):642-646.

[3]. Glennon RA, et al. 5-HT1 and 5-HT2 binding characteristics of some quipazine analogues. J Med Chem. 1986 Nov;29(11):2375-80.

[4]. Ireland SJ, Tyers MB. Pharmacological characterization of 5-hydroxytryptamine-induced depolarization of the rat isolated vagus nerve. Br J Pharmacol. 1987 Jan;90(1):229-38.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
403.7±25.0 °C at 760 mmHg

[ Melting Point ]:
120-122 °C(lit.)

[ Molecular Formula ]:
C₂₁H₂₃N₃O₈

[ Molecular Weight ]:
213.278

[ Flash Point ]:
198.0±23.2 °C

[ Exact Mass ]:
213.126602

[ PSA ]:
177.36000

[ LogP ]:
1.59

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.629

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VC2513500

CHEMICAL NAME :: Quinoline, 2-(1-piperazinyl)-

CAS REGISTRY NUMBER :: 4774-24-7

BEILSTEIN REFERENCE NO. :: 0196945

LAST UPDATED :: 199712

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C13-H15-N3

MOLECULAR WEIGHT :: 213.31

WISWESSER LINE NOTATION :: T66 BNJ C- AT6N DNTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 296 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DDREDK Drug Development Research. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1981- Volume(issue)/page/year: 3,357,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 135 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 28,1394,1985

Safety Information

[ RTECS ]:
VC2513500

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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