ChemicalBook > CAS DataBase List > Nitidine chloride

Nitidine chloride

Nitidine chloride Structure
Nitidine chloride
  • CAS No.13063-04-2
  • Chemical Name:Nitidine chloride
  • CBNumber:CB4341347
  • Molecular Formula:C21H18NO4+
  • Formula Weight:348.37
  • MOL File:13063-04-2.mol
Nitidine chloride Property
  • Melting point 283-286 °C
  • storage temp. -20°C
  • solubility DMSO: soluble1mg/mL, clear (warmed)
  • form powder
  • color white to beige
  • InChIKey QLDAACVSUMUMOR-UHFFFAOYSA-M
  • FDA UNII XO8WQL69T8
  • UNSPSC Code 12352200
  • NACRES NA.77
Safety
  • Safety Statements  :24/25
  • WGK Germany  :3
  • RTECS  :DF4935500
  • HS Code  :29399990
  • Toxicity :mouse,LD50,intraperitoneal,98980ug/kg (98.98mg/kg),National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
  • NFPA 704:
    0
    4 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H300
  • Precautionary statements P264-P270-P301+P310-P321-P330-P405-P501

Nitidine chloride Chemical Properties,Usage,Production

  • Description This quaternary alkaloid occurs primarily in Zanthoxylum nitidum (Lam.) DC but has also been found in several species of Fagara. It is normally isolated as the chloride which forms bright yellow needles when recrystallized from EtOH-HCl. The crystals decompose on heating to 240°C yielding a product having m.p. 285-6°C. The iodide also forms yellow needles and undergoes a similar trans_x0002_formation at the same temperature to yield a product with the same melting point, possibly identical to that obtained from the chloride. The crystalline acetate, m.p. 255-260°C and the pseudocyanide, m.p. 215-6°C and decomposing completely at 234°C in vacuo have also been prepared. A periodide, which fonns chocolate-brown needles when crystallized from Me2CO, m.p. 300-1 °c (dec.) is useful for characterizing the base.
  • Uses Nitidine Chloride shows the ability to inhibit hepatic cancer growth through modulation of signaling pathways.
  • Preparation A solution of 1555 (0.102 g, 0.278 mmol) and triphosgene (0.179 g, 0.602 mmol) in acetonitrile (2.5 mL) was stirred at 60 C° (bath temperature) for 0.5 h. After the addition of ice/water, a yellow precipitate was collected by filtration and recrystallized from ethanol/diethyl ether to directly afford nitidine chloride (0.098 g, 91%); mp 285–292 C°.
    13063-04-2 synthesis
    An isocyano group can serve as both a protecting group for the amino function, and, due to its electronic effect, as an activating group as well. These two functionalities are employed in a synthetic route whereby an amino function has to be protected and a condensation reaction is performed at the a-carbon atom, for which activation is required.
    3,4-Fused tryptophan analogues 1563 and 1564 contain a ring that bridges the a-carbon and the 4-position of the indole ring, thus limiting the conformational flexibility of the side chain. The synthesis proceeds from N-formylated 40-bromotryptophan 1558 via isocyanide 1559, 2-propenoate 1560, and Pd-catalyzed cyclization of the a-2-propenyl dl-tryptophan derivatives 1561 and 1562 to give both the seven- and eight-membered constrained ring analogues 1564 and 1563. Dehydration of the formamide 1558 with triphosgene affords the isocyanide 1559 in 75% (87%) yield.
  • Biochem/physiol Actions Nitidine chloride is a natural product with anti-cancer activity. Its mechanism of action likely involves several pathways. Nitidine chloride has been found to inhibit topoisomerase I and topoisomerase II, induce cell apoptosis by activation of the caspase-dependent pathway, suppress c-Src/FAK associated signaling pathways and suppress Janus kinase 2/STAT3 signaling and the expression of STAT3-dependent target genes, including cyclin D1, Bcl-xL, and VEGF. Nitidine chloride has also been found to have anti-malaria activity.
  • in vivo

    Nitidine chloride (5 mg/kg, intraperitoneal injection, once daily, 5 weeks) inhibits tumor growth in mice and induces apoptosis in renal cancer cells in vivo[1].
    Nitidine chloride (0.375-10 mg/kg, intraperitoneal injection, once daily, 3 weeks) downregulates hypertrophy in mouse myocardium through AGT4B-mediated autophagy[3].
    Nitidine chloride (5-10 mg/kg, intraperitoneal injection, single dose) exerts anti-inflammatory effects in endotoxin-treated mice through Akt-mediated IL-10 production[4].

    Animal Model:A549 nude mouse xenograft model[1]
    Dosage:5 mg/kg; daily; 5 weeks
    Administration:Intraperitoneal injection (i.p.)
    Result:Showed non-toxic effects, reduced tumor growth, and induced apoptosis in renal cancer cells in vivo.
    Animal Model:Mice, beagles[3]
    Dosage:2.5, 5, 10 mg/kg; 0.375, 0.75, 1.5 mg/kg; daily; 4 weeks
    Administration:Intraperitoneal injection (i.p.)
    Result:Both induced dose-dependent cardiac hypertrophy and dysfunction, while medium and high doses led to death in beagle dogs. Cardiac autophagy levels in cardiomyocytes were reduced. Overexpression of ATG4B reversed cardiac hypertrophy and reduced autophagy levels.
    Animal Model:LPS induced endotoxemic mice[4]
    Dosage:5, 10 mg/kg; single dose
    Administration:Intraperitoneal injection (i.p.)
    Result:Increased IL-10 production, inhibited inflammatory response, reduced mortality, and enhanced Akt activation.
  • IC 50 Plasmodium
  • References Arthur, Hui, Ng., Chern. Ind., 1514 (1958)
    Arthur, Hui, Ng.,J. Chern. Soc., 1840 (1959)
    Kuck, Albonico, Deulofeu., Chern. Ind., 945 (1966)
Nitidine chloride Preparation Products And Raw materials
Raw materials
Preparation Products
Nitidine chloride Suppliers
Global(237)Suppliers
  • Supplier：
    career henan chemical co
  • Tel：+86-0371-86658258<br/>+8613203830695
  • Email：sales@coreychem.com
  • Country：China
  • ProdList：29859
  • Advantage：58
  • Supplier：
    BOC Sciences
  • Tel：+1-631-485-4226
  • Email：inquiry@bocsci.com
  • Country：United States
  • ProdList：19552
  • Advantage：58
Nitidine chloride Spectrum
13063-04-2, Nitidine chlorideRelated Search:
  • standardized herbal extract
  • reference standards from Chinese medicinal herbs (TCM).
  • phytochemical
  • pharmaceutical intermediate
  • chemical reagent
  • Active Pharmaceutical Ingredients
  • 生物碱类
  • 抑制剂
  • 试剂
  • 高端化学
  • 标准品，对照品
  • 标准品 -中药标准品
  • 分析试剂-对照品
  • 原料
  • 标准品-中药标准品
  • 原料药
  • 分析试剂标准品
  • 标准品-对照品
  • 植物提取物
  • 分析标准品
  • 对照品,标准品
  • 中药标准品
  • 植提标准品
  • 对照品
  • 标准品
  • 中药对照品
  • C21H17NO4HCl
  • 13113063-02-2
  • NITIDINE CHLORIDE(氯化两面针碱) |CAS 13063-04-2
  • 氯化两面针碱/生物碱类
  • 2,3-二甲氧基-12-甲基-[1,3]二氧杂环戊[4',5':4,5]苯并[1,2-C]菲啶-12-鎓氯化物
  • 标准品对照品】NITIDINE CHLORIDE
  • 氯化两面针碱(对照品)
  • 氯化两面针碱NITIDINE CHLORIDE
  • 氯化两面针碱, 来源于两面针
  • 2,3-二甲氧基-12-甲基-(1,3)-苯并二恶茂并(5,6-c)菲啶鎓氯化物
  • 氯化两面针碱
  • 2,3-二甲氧基-12-甲基-(1,3)-苯并二恶茂并(5,6-C)菲啶氯化物
  • 光叶花椒碱
  • 氯化两面针碱(标准品)
  • 6-C)菲啶鎓氯化物
  • 3-二甲氧基-12-甲基-(1
  • 3)-苯并二恶茂并(5
  • NITIDINE CHLORIDE 氯化两面针碱
  • 13063-04-2
  • 2,3-Dimethoxy-12-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium chloride
  • 1,3]Benzodioxolo[5,6-c]phenanthridinium, 2,3-dimethoxy-12-methyl-, chloride (1:1)
  • Nitidine, chloride (6CI, 7CI, 8CI)
  • ShinyleafPricklyashRoot
  • Nitidine chloride, 98%, from Zanthoxylum nitidum (Roxb.) DC.
  • NITIDINE CHLORIDE (RG)
  • Angolinine
  • NITIDINE
  • dimethoxy-12-methyl-,chloride
  • [1,3]Dioxolo[4,5]benzo[1,2-c]phenanthridinium, 2,3-
  • Nitidine chloride
  • 2,3-Dimethoxy-12-methyl-(1,3)-benzodioxolo(5,6-c)phenanthridinium chloride

Home

My