2,4-DINITROCHLOROBENZENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H3ClN2O4
Molecular Weight	202.552
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)C1=CC(=C(Cl)C=C1)[N+]([O-])=O

InChI

InChIKey=VYZAHLCBVHPDDF-UHFFFAOYSA-N

InChI=1S/C6H3ClN2O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H

HIDE SMILES / InChI

Molecular Formula	C6H3ClN2O4
Molecular Weight	202.552
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3977355 | https://www.ncbi.nlm.nih.gov/pubmed/31018627 | http://www.aidsinfonet.org/fact_sheets/view/725 | https://www.ncbi.nlm.nih.gov/pubmed/6084926 | https://my.clevelandclinic.org/health/articles/warts/warts-treatment | https://www.ncbi.nlm.nih.gov/pubmed/4830106

Dinitrochlorobenzene (DNCB) is a chemical used in color photography processing. Dinitrochlorobenzene has been successfully used to treat warts. It requires follow-up applications that might be done either in the office by the doctor or a nurse, or at home by the patient. The therapy was working immunologically to enable the body to recognize the foreign virus. The cure is associated with normalization of the cell-mediated immune response. Some researchers and community activists proposed that when DNCB is applied to the skin once a week, it stimulates the immune system to control HIV replication and delay opportunistic infections. Some research shows that DNCB leads to increases in CD8 (T-killer or T-8) cells. Dinitrochlorobenzene is not approved by the FDA, and is considered experimental. There are possible drawbacks to this treatment. The autoeczematization is not rare. Dinitrochlorobenzene is used to induce experimental dermatitis in rats. It is a potent contact allergen.

Approval Year

PubMed

Title	Date	PubMed
Mu-class glutathione transferase from Xenopus laevis: molecular cloning, expression and site-directed mutagenesis.	2002-08-01	11991804
Inhibition of glutathione S-transferase in rat hepatocytes by a glycine-tetrazole modified S-alkyl-GSH analogue.	2002-06-17	12039566
Reversible inactivation of the tumor suppressor PTEN by H2O2.	2002-06-07	11916965
Aromatic residues in the C-terminal region of glutathione transferase A1-1 influence rate-determining steps in the catalytic mechanism.	2002-05-20	12009415
Active-site residues governing high steroid isomerase activity in human glutathione transferase A3-3.	2002-05-10	11872752
Expression and characterisation of a Psoroptes ovis glutathione S-transferase.	2002-04-19	11879966
Fluorometric microplate assay to measure glutathione S-transferase activity in insects and mites using monochlorobimane.	2002-04-15	11950219
Glutamic acid-65 is an essential residue for catalysis in Proteus mirabilis glutathione S-transferase B1-1.	2002-04-01	11903062
Susceptibility and detoxifying enzyme activity in two spider mite species (Acari: Tetranychidae) after selection with three insecticides.	2002-04	12020020
Purification and characterisation of glutathione S-transferases from the freshwater clam Corbicula fluminea (Müller).	2002-04	11976063
Topical immunotherapy with contact sensitizers for viral warts.	2002-04	11966711
Expression and characterization of a novel class of glutathione S-transferase from Anopheles dirus.	2002-04	11886777
Cytokine profiling for chemical sensitizers: application of the ribonuclease protection assay and effect of dose.	2002-03-15	11906244
Ebselen has dehydroascorbate reductase and thioltransferase-like activities.	2002-03-01	11855823
Formation of murine macrophage-derived 5-oxo-7-glutathionyl-8,11,14-eicosatrienoic acid (FOG7) is catalyzed by leukotriene C4 synthase.	2002-03-01	11748223
The organochlorine pesticide residues and antioxidant enzyme activities in human breast tumors: is there any association?	2002-03	12038708
Isolation and characterization of glutathione-S-transferase isozyme Q3 from the northern quahog, Mercinaria mercinaria.	2002-03	12018616
Glutathione S-transferase isoenzymes in the two-spot ladybird, Adalia bipunctata (Coleoptera: Coccinellidae).	2002-03	11857676
Hybridization of alpha class subunits generating a functional glutathione transferase A1-4 heterodimer.	2002-02-15	11851347
Relationship between 2,4-dinitrochlorobenzene elicitation responses and individual irritant threshold.	2002-02	11918603
Comparative study of the purification and characterization of the cytosolic glutathione S-transferases from two salmonid species: Atlantic salmon (Salmo salar) and brown trout (Salmo trutta).	2002-02	11879788
Induced changes in total serum IgE concentration in the Brown Norway rat: potential for identification of chemical respiratory allergens.	2002-01-25	11807923
The toxicity of tri-substituted benzenes to the protozoan ciliate Spirostomum ambiguum.	2002-01	11827293
Role of the glutamyl alpha-carboxylate of the substrate glutathione in the catalytic mechanism of human glutathione transferase A1-1.	2001-12-25	11747461
Reactive oxygen species, antioxidants, and the mammalian thioredoxin system.	2001-12-01	11728801
GSH depletion, K-Cl cotransport, and regulatory volume decrease in high-K/high-GSH dog red blood cells.	2001-12	11698259
Characterisation of polymeric surfactants that are glutathione transferase mimics.	2001-11-30	11684322
Assessment of preferential Th1 or Th2 induction by low-molecular-weight compounds using a reverse transcription-polymerase chain reaction method: comparison of two mouse strains, C57BL/6 and BALB/c.	2001-11-15	11708898
Decreased glutathione S-transferase expression and activity and altered sex steroids in Lake Apopka brown bullheads (Ameiurus nebulosus).	2001-11-12	11595311
Detection and characterization of glutathione S-transferase activity in rice EF-1betabeta'gamma and EF-1gamma expressed in Escherichia coli.	2001-11-02	11676472
A new approach for dynamics of enzyme-catalyzed glutathione conjugation by electrospray quadrupole/time-of-flight mass spectrometry.	2001-11-01	11673899
Mammalian class Sigma glutathione S-transferases: catalytic properties and tissue-specific expression of human and rat GSH-dependent prostaglandin D2 synthases.	2001-11-01	11672424
Yeast cys3 and gsh1 mutant cells display overlapping but non-identical symptoms of oxidative stress with regard to subcellular protein localization and CDP-DAG metabolism.	2001-11	11713678
Role of multidrug resistance protein 2 (MRP2) in glutathione-bimane efflux from Caco-2 and rat renal proximal tubule cells.	2001-11	11682439
Hypochlorous acid is a potent inhibitor of GST P1-1.	2001-10-25	11640916
Requirement for GSH in recycling of ascorbic acid in endothelial cells.	2001-10-01	11543722
Topical immunomodulators--progress towards treating inflammation, infection, and cancer.	2001-10	11871495
Cytokine expression profiles during murine contact allergy: T helper 2 cytokines are expressed irrespective of the type of contact allergen.	2001-10	11757671
Proposed reductive metabolism of artemisinin by glutathione transferases in vitro.	2001-10	11697139
Effect of food reductones, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and hydroxyhydroquinone (HHQ), on lipid peroxidation and type IV and I allergy responses of mouse.	2001-10	11600049
Evaluation of skin sensitization potential of melatonin and nimesulide by murine local lymph node assay.	2001-10	11576826
Purification and characterization of a glutathione S-transferase from the fungus Cunninghamella elegans.	2001-09-25	11583857
Langerhans cells and immature dendritic cells as model systems for screening of skin sensitizers.	2001-09-22	11566557
Immunohistochemical detection of protein adducts of 2,4-dinitrochlorobenzene in antigen presenting cells and lymphocytes after oral administration to mice: lack of a role of Kupffer cells in oral tolerance.	2001-09	11559035
The therapeutic use of topical contact sensitizers in benign dermatoses.	2001-09	11531828
Rapid allergen delivery with photomechanical waves for inducing allergic skin reactions in the hairless guinea pig animal model.	2001-09	11526522
Energy-dependent export of the 13-oxooctadecadienoic acid-glutathione conjugate from HT-29 cells and plasma membrane vesicles.	2001-08-29	11514236
CD1a-positive dendritic cells transport the antigen DNCB intracellularly from the skin to the regional lymph nodes in the induction phase of allergic contact dermatitis.	2001-08	11686518
Influence of reduced intracellular glutathione availability on the secretion of vasoactive substances by human umbilical vein endothelial cells.	2001	12044313
Simultaneous identification of GSTP1 Ile105-->Val105 and Ala114-->Val114 substitutions using an amplification refractory mutation system polymerase chain reaction assay: studies in patients with asthma.	2001	11686891

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:01 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:01 GMT 2025`
Record UNII	GE3IBT7BMN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

1-CHLORO-2,4-DINITROBENZENE

Preferred Name

English

2,4-DINITROCHLOROBENZENE

Systematic Name

English

DINITROCHLOROBENZENE

Systematic Name

English

1-CHLORO-2,4-DINITROBENZENE [HSDB]

Common Name

English

DNCB

Common Name

English

2,4-DINITROCHLOROBENZENE [MART.]

Common Name

English

NSC-6292

Code

English

1-chloro-2,4-dinitrobenzene [WHO-DD]

Common Name

English

BENZENE, 1-CHLORO-2,4-DINITRO-

Systematic Name

English

1-CHLORO-2,4-DINITROBENZENE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1937