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Nitidine chloride

Product Name
Nitidine chloride
CAS No.
13063-04-2
Chemical Name
Nitidine chloride
Synonyms
NITIDINE;Angolinine;Nitidine chloride;NITIDINE CHLORIDE (RG);ShinyleafPricklyashRoot;dimethoxy-12-methyl-,chloride;Nitidine, chloride (6CI, 7CI, 8CI);[1,3]Dioxolo[4,5]benzo[1,2-c]phenanthridinium, 2,3-;Nitidine chloride, 98%, from Zanthoxylum nitidum (Roxb.) DC.;2,3-Dimethoxy-12-methyl-(1,3)-benzodioxolo(5,6-c)phenanthridinium chloride
CBNumber
CB4341347
Molecular Formula
C21H18NO4+
Formula Weight
348.37
MOL File
13063-04-2.mol
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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
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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,
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H300Fatal if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
29223
Product name
Nitidine (chloride)
Packaging
10mg
Price
$107
Updated
2024/03/01
Cayman Chemical
Product number
29223
Product name
Nitidine (chloride)
Packaging
100mg
Price
$929
Updated
2024/03/01
Cayman Chemical
Product number
29223
Product name
Nitidine (chloride)
Packaging
5mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
29223
Product name
Nitidine (chloride)
Packaging
25mg
Price
$249
Updated
2024/03/01
TRC
Product number
N490110
Product name
Nitidine chloride
Packaging
25mg
Price
$295
Updated
2021/12/16
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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°.

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.

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

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Nitidine chloride Suppliers

China 202 Germany 1 India 2 United Kingdom 3 United States 18 Global 226
ALB Technology Limited
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View Lastest Price from Nitidine chloride manufacturers

Shaanxi Haibo Biotechnology Co., Ltd
Product
Nitidine chloride 13063-04-2
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
2000ton
Release date
2023-08-24
Shanghai Standard Technology Co., Ltd.
Product
Nitidine Chloride 13063-04-2
Price
US $0.00/mg
Min. Order
5mg
Purity
≥97%(HPLC)
Supply Ability
10 g
Release date
2019-09-24
Career Henan Chemical Co
Product
Nitidine chloride 13063-04-2
Price
US $1.00/kg
Min. Order
1g
Purity
99%
Supply Ability
100KG
Release date
2018-12-25

13063-04-2, Nitidine chlorideRelated Search:

Tribenuron methyl Thionyl chloride DIMETHYLPHOSPHINOTHIOIC CHLORIDE Sodium chloride Dimethoxymethane Potassium chloride Choline chloride Calcium chloride Ammonium chloride Methyl acetate Kresoxim-methyl 2,6-Dimethoxybenzaldehyde METSULFURON METHYL Methyl salicylate Thiophanate-methyl 2,2-Dimethoxypropane Polyvinyl chloride Dimethyldimethoxysilane

  • 2,3-Dimethoxy-12-methyl-(1,3)-benzodioxolo(5,6-c)phenanthridinium chloride
  • Nitidine chloride
  • [1,3]Dioxolo[4,5]benzo[1,2-c]phenanthridinium, 2,3-
  • dimethoxy-12-methyl-,chloride
  • NITIDINE
  • 2,3-DiMethoxy-12-Methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-12-iuM chloride
  • Angolinine
  • NITIDINE CHLORIDE (RG)
  • Nitidine chloride, 98%, from Zanthoxylum nitidum (Roxb.) DC.
  • ShinyleafPricklyashRoot
  • Nitidine, chloride (6CI, 7CI, 8CI)
  • 1,3]Benzodioxolo[5,6-c]phenanthridinium, 2,3-dimethoxy-12-methyl-, chloride (1:1)
  • 2,3-Dimethoxy-12-methyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-c]phenanthridin-12-ium chloride
  • 13063-04-2
  • 13113063-02-2
  • C21H17NO4HCl
  • Active Pharmaceutical Ingredients
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract