Nitidine chloride

Names

[ Name ]:
Nitidine chloride

[Synonym ]:
2,3-Dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium chloride
[1,3]Benzodioxolo[5,6-c]phenanthridinium, 2,3-dimethoxy-12-methyl-, chloride (1:1)
2,3-Dimethoxy-12-methyl[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium chloride
Nitidine chloride
2,3-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridin-12-ium,chloride

Biological Activity

[Description]:

Nitidine chloride, a potential anti-malarial lead compound derived from Zanthoxylum nitidum (Roxb) DC, exerts potent anticancer activity through diverse pathways, including inducing apoptosis, inhibiting STAT3 signaling cascade, DNA topoisomerase 1 and 2A, ERK and c-Src/FAK associated signaling pathway. Nitidine chloride inhibits LPS-induced inflammatory cytokines production via MAPK and NF-kB pathway[1][2][3][4][5][6].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Signaling Pathways >> Stem Cell/Wnt >> STAT

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase

Signaling Pathways >> JAK/STAT Signaling >> STAT

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> FAK

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Research Areas >> Inflammation/Immunology

Signaling Pathways >> MAPK/ERK Pathway >> ERK

Signaling Pathways >> Stem Cell/Wnt >> ERK

[References]

[1]. Chen J, et al. Inhibition of STAT3 signaling pathway by nitidine chloride suppressed the angiogenesis and growth of human gastric cancer. Mol Cancer Ther. 2012 Feb;11(2):277-87.

[2]. Wang Z, et al. Nitidine chloride inhibits LPS-induced inflammatory cytokines production via MAPK and NF-kappaB pathway in RAW 264.7 cells. J Ethnopharmacol. 2012 Oct 31;144(1):145-50.

[3]. Pan X, et al. Nitidine Chloride inhibits breast cancer cells migration and invasion by suppressing c-Src/FAK associated signaling pathway. Cancer Lett. 2011 Dec 27;313(2):181-91.

[4]. Fang Z, et al. Nitidine chloride induces apoptosis and inhibits tumor cell proliferation via suppressing ERK signaling pathway in renal cancer. Food Chem Toxicol. 2014 Apr;66:210-6.

[5]. Liu LM, et al. DNA topoisomerase 1 and 2A function as oncogenes in liver cancer and may be direct targets of nitidine chloride. Int J Oncol. 2018 Nov;53(5):1897-1912.

[6]. Bouquet J, et al. Biological activities of nitidine, a potential anti-malarial lead compound. Malar J. 2012 Mar 9;11:67.

Chemical & Physical Properties

[ Density]:
1.35g/cm3

[ Boiling Point ]:
619ºC at 760 mmHg

[ Melting Point ]:
281-282ºC

[ Molecular Formula ]:
C₂₁H₁₈ClNO₄

[ Molecular Weight ]:
383.825

[ Flash Point ]:
189.4ºC

[ Exact Mass ]:
383.092438

[ PSA ]:
40.80000

[ LogP ]:
3.71660

[ Appearance of Characters ]:
white to beige

[ Vapour Pressure ]:
3.01E-15mmHg at 25°C

[ Index of Refraction ]:
1.696

[ Storage condition ]:
?20°C

[ Water Solubility ]:
DMSO: soluble1mg/mL, clear (warmed)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DF4935500

CHEMICAL NAME :: (1,3)-Benzodioxolo(5,6-c)phenanthridinium, 2,3-dimethoxy-12-methyl-, chloride

CAS REGISTRY NUMBER :: 13063-04-2

LAST UPDATED :: 199410

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C21-H18-N-O4.Cl

MOLECULAR WEIGHT :: 383.85

WISWESSER LINE NOTATION :: T G5 E6 B666 HO JO OK IHJ O1 SO1 TO1 &G

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 98980 ug/kg

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

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 40 ug/plate

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 66,1781,1977

Safety Information

[ Safety Phrases ]:
24/25

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DF4935500

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Nitidine chloride inhibits hepatocellular carcinoma cell growth in vivo through the suppression of the JAK1/STAT3 signaling pathway.

Int. J. Mol. Med. 32(1) , 79-84, (2013)

Signal transducer and activator of transcription 3 (STAT3) is persistently activated in cancer cells and contributes to malignant progression in various types of cancer. The Janus-activated kinase (JA...

Alkaloids, amides and antispasmodic activity of Zanthoxylum hyemale.

Planta Med. 68(6) , 534-8, (2002)

Two quinoline alkaloids, (-)-R-geilbalansine (1) and hyemaline (2), as well as aromatic amide, N-[2-(3,4-dimethoxyphenyl)-2-methoxyethyl)-2-methoxyethyl]benzamide (O-methylbalsamide) (3), were isolate...

The role of the iminium bond in the inhibition of reverse transcriptase by quaternary benzophenanthridines.

J. Pharm. Pharmacol. 50(11) , 1307-15, (1998)

The quaternary benzo[c]phenanthridines fagaronine, nitidine and O-methylfagaronine have been reviewed as potential antitumour and antiviral agents. Their mode of action has not been established, but t...

Related Compounds

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