Quinacrine dihydrochloride - ≥98% , CAS No.69-05-6

CAS: 69-05-6 Cat. No.: Q113496 Peso molecular: 472.88 Beilstein Registry Number: 4834013 Número EC: 200-700-8 PubChem CID: 6239

GRADE & PURITY ≥98%

Synonyms

N4-(6-chloro-2-methoxyacridin-9-yl)-N1,N1-diethylpentane-1,4-diamine dihydrochloride | 4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine;dihydrochloride | Q0056 | UDKVBVICMUEIKS-UHFFFAOYSA-N | EINECS 200-700-8 | MEPACRINE HYDROCHLORI

Storage

Protected from light,Room temperature

Shipped In

Normal

Descripción general

Quinacrine dihydrochloride is a non-specific PLA2 (phospholipase A2) inhibitor. Quinacrine, Dihydrochloride acts as an AChR (acetylcholine receptor) antagonist. Quinacrine dihydrochloride suppresses glibenclamide-sensitive K+-currents (IC50 = 4.4 μM). This compound also inhibits MAO (monoamine oxidase). Quinacrine, Dihydrochloride is an inhibitor of cPLA2, MAO-A and MAO-B.
A non-specific PLA2 inhibitor. and acetylcholine receptor antagonist

Application：

Quinacrine dihydrochloride has been used:

in its uptake and accumulation studies in mouse lung slices using fluorescence microscope

in the staining of ATP vesicles in mesenchymal stem cells (MSCs)

in uptake-release assay for characterization of dense granule functionality of platelets

Specifications

Sinónimos

N4-(6-chloro-2-methoxyacridin-9-yl)-N1, N1-diethylpentane-1, 4-diamine dihydrochloride | 4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N, 1-N-diethylpentane-1, 4-diamine;dihydrochloride | Q0056 | UDKVBVICMUEIKS-UHFFFAOYSA-N | EINECS 200-700-8 | MEPACRINE HYDROCHLORI

Especificaciones y pureza

≥98%

Mecanismos bioquímicos y fisiológicos

It can be used for female sterilization. For the treatment of systemic lupus erythematosus and rheumatic diseases. Apart from malaria, it is effective for the treatment of Giardia and Taenia infection. Besides inhibiting monoamine oxidase, it can also inh

Condiciones de almacenamiento de almacenamiento

Protected from light, Room temperature

Enviado en

Normal

Nota

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 488180027
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488180027
• Sonrisas canónicas: CCN(CC)CCCC(C)NC1=C2C=C(C=CC2=NC3=C1C=CC(=C3)Cl)OC.Cl.Cl
• IUPAC Name: 4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine;dihydrochloride
• InChIKey: UDKVBVICMUEIKS-UHFFFAOYSA-N
• INCHI: 1S/C23H30ClN3O.2ClH/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23;;/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26);2*1H
• Isómeros SMILES: CCN(CC)CCCC(C)NC1=C2C=C(C=CC2=NC3=C1C=CC(=C3)Cl)OC.Cl.Cl
• WGK Alemania: 3
• RTECS: AR7875000
• PubChem CID: 6239
• Peso molecular: 472.88
• Beilstein: 4834013
• Reaxy-Rn: 4834013

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Quinolines and derivatives
      • Subclass Benzoquinolines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Quinolines and derivatives
• Subclass: Benzoquinolines
• Intermediate Tree Nodes: Not available
• Direct Parent: Acridines
• Alternative Parents: Chloroquinolines 4-aminoquinolines Anisoles Secondary alkylarylamines Aminopyridines and derivatives Alkyl aryl ethers Aryl chlorides Heteroaromatic compounds Trialkylamines Azacyclic compounds Organopnictogen compounds Organochlorides Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Acridine - 4-aminoquinoline - Haloquinoline - Aminoquinoline - Chloroquinoline - Anisole - Alkyl aryl ether - Aminopyridine - Secondary aliphatic/aromatic amine - Aryl chloride - Aryl halide - Pyridine - Benzenoid - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Secondary amine - Azacycle - Ether - Hydrochloride - Organohalogen compound - Organochloride - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Hydrocarbon derivative - Organooxygen compound - Amine - Organopnictogen compound - Aromatic heteropolycyclic compound
• Descripción: This compound belongs to the class of organic compounds known as acridines. These are organic compounds containing the acridine moiety, a linear tricyclic heterocycle which consists of two benzene rings joined by a pyridine ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

VDR Tclin Vitamin D receptor (26531 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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POLB Tchem DNA polymerase beta (23632 Activities)

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TRPV1 Tclin Vanilloid receptor (8273 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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HBB Tbio Hemoglobin beta chain (329 Activities)

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CASP1 Tchem Caspase-1 (6235 Activities)

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ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

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CASP7 Tchem Caspase-7 (3146 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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MT4 (17854 Activities)

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HEK293 (82097 Activities)

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HepG2 (196354 Activities)

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HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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POLH Tchem DNA polymerase eta (21678 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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ORM2 Tbio Alpha-1-acid glycoprotein 2 (1 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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TRPM7 Tchem Transient receptor potential cation channel subfamily M member 7 (19 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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USP2 Tbio Ubiquitin carboxyl-terminal hydrolase 2 (8818 Activities)

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SMN1 Tchem Survival motor neuron protein (34246 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)

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GMNN Tbio Geminin (128009 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 Activities)

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MBNL1 Tbio Muscleblind-like protein 1 (34431 Activities)

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MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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Objetivos asociados (no humanos)

Plasmodium falciparum (966862 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Calf thymus DNA (4845 Activities)

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GCN5 Histone acetyltransferase GCN5 (89 Activities)

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Npsr1 Neuropeptide S receptor (260 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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FTL Ferritin light chain (43324 Activities)

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nfo Endonuclease 4 (425 Activities)

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NS1 Nonstructural protein 1 (33327 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in water (50 mg/ml with heat, yielding a clear solution), and ethanol (slightly). Insoluble in alcohol, benzene, chloroform, and ether.
• Sensibilidad: Light sensitive
• Punto de fusión (°C): 257℃
• Peso molecular: 472.900 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 471.161 Da
• Monoisotopic Mass: 471.161 Da
• Topological Polar Surface Area: 37.400 Ų
• Heavy Atom Count: 30
• Formal Charge: 0
• Complexity: 461.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3

Referencias

1. Siyuan Lu, Jing Chen, Junyuan Wang, Donghui Wu, Hongfeng Bian, Haibo Jiang, Lianxi Sheng, Chunguang He.  (2022)  Toxicological effects and transcriptome mechanisms of rice (Oryza sativa L.) under stress of quinclorac and polystyrene nanoplastics.  ECOTOXICOLOGY AND ENVIRONMENTAL SAFETY,      [PMID:36508812] [10.1016/j.ecoenv.2022.114380]

2. Xiaofei Ma, Jing Cao, Juan Yu, Liangliang Cai.  (2022)  Evaluation of an ionic liquid chiral selector based on sulfobutylether-β-cyclodextrin in capillary electrophoresis.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2022.119782]

3. Ruirui Qi, Yang Su, Leilei Pan, Yuqi Mao, Lu Liang, Zhiqiang Dai, Junqin Wang, Yiling Cai.  (2018)  Anti-cholinergics mecamylamine and scopolamine alleviate motion sickness-induced gastrointestinal symptoms through both peripheral and central actions.  NEUROPHARMACOLOGY,      [PMID:30543811] [10.1016/j.neuropharm.2018.12.006]

4. Zhuo Li, Boguang Yang, Zhengmeng Yang, Xian Xie, Zhengnan Guo, Jianyang Zhao, Ruinan Wang, Hao Fu, Pengchao Zhao, Xin Zhao, Guosong Chen, Gang Li, Fuxin Wei, Liming Bian.  (2024)  Supramolecular Hydrogel with Ultra-Rapid Cell-Mediated Network Adaptation for Enhancing Cellular Metabolic Energetics and Tissue Regeneration.  ADVANCED MATERIALS,      [PMID:38295393] [10.1002/adma.202307176]