Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H8N2 |
| Molecular Weight | 108.1411 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=CC=C(N)C=C1
InChI
InChIKey=CBCKQZAAMUWICA-UHFFFAOYSA-N
InChI=1S/C6H8N2/c7-5-1-2-6(8)4-3-5/h1-4H,7-8H2
| Molecular Formula | C6H8N2 |
| Molecular Weight | 108.1411 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26663148 | https://www.ncbi.nlm.nih.gov/pubmed/24602904
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26663148 | https://www.ncbi.nlm.nih.gov/pubmed/24602904
p-Phenylenediamine is one of the simplest aromatic diamine primarily used as a component of engineering polymers, composites, dye intermediate and as a hair dye. p-Phenylenediamine is easily oxidized, and for this reason derivatives of p-Phenylenediamine are used as antiozonants in the production of rubber products. The substituents, naphthyl, isopropyl etc. affect the effectiveness of their antioxidant roles as well as their properties as skin irritants. Acute (short-term) exposure to high levels of p-phenylenediamine may cause severe dermatitis, eye irritation and asthma, gastritis, renal failure, vertigo, tremors, convulsions, and coma in humans. Eczematoid contact dermatitis may result from chronic (long-term) exposure in humans. In rats and mice chronically exposed to p-phenylenediamine in their diet, depressed body weights, but no other clinical signs of toxicity were observed in several studies. No information is available on the reproductive, developmental, or carcinogenic effects of p-phenylenediamine in humans. EPA has not classified p-phenylenediamine with respect to carcinogenicity.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Urinary acetylated metabolites and N-acetyltransferase-2 genotype in human subjects treated with a para-phenylenediamine-containing oxidative hair dye. | 2004-11 |
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| Allergic contact dermatitis from para-phenylenediamine in Bigen powder hair dye. | 2004-08 |
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| Synthesis and cytotoxic evaluation of two novel anthraquinone derivatives. | 2004-08 |
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| Environmental contact factors in eczema and the results of patch testing Chinese patients with a modified European standard series of allergens. | 2004-07 |
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| Allergic contact dermatitis from hair dye and development of lichen simplex chronicus. | 2004-07 |
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| Hair dye contact allergy: quantitative exposure assessment of selected products and clinical cases. | 2004-06 |
|
| Acute renal failure following para-phenylenediamine (PPD) poisoning: a case report and review. | 2004-05 |
|
| Reproducibility of patch test results: a concurrent right-versus-left study using TRUE Test. | 2004-05 |
|
| Characterization of the sensitizing potential of chemicals by in vitro analysis of dendritic cell activation and skin penetration. | 2004-05 |
|
| Contact dermatitis and other skin conditions in instrumental musicians. | 2004-04-16 |
|
| Efficient cancer therapy with a nanobody-based conjugate. | 2004-04-15 |
|
| Improving the biological nitrogen removal process in pharmaceutical wastewater treatment plants: a case study. | 2004-04 |
|
| Adhesion and proliferation of cells on new polymers modified biomaterials. | 2004-04 |
|
| Synthesis and antiproliferative activity of some new DNA-targeted alkylating pyrroloquinolines. | 2004-02-15 |
|
| Allergic contact dermatitis caused by the clothing dye, disperse blue 106, an important contact allergen that may be frequently missed. | 2004-02 |
|
| Hydrogen bond-induced rigid oligoanthranilamide ribbons that are planar and straight. | 2004-01-22 |
|
| Synthesis and evaluation of nitroheterocyclic carbamate prodrugs for use with nitroreductase-mediated gene-directed enzyme prodrug therapy. | 2003-12-04 |
|
| Xanthelasma palpebrarum following allergic contact dermatitis from para-phenylenediamine in a black eyelash-tinting product. | 2003-12 |
|
| Relevance of positive patch test reactions in patients attending a dermatology tertiary referral centre. | 2003-11 |
|
| Contact allergy to ingredients of hair cosmetics in female hairdressers and clients--an 8-year analysis of IVDK data. | 2003-11 |
|
| Thiol antioxidants block the activation of antigen-presenting cells by contact sensitizers. | 2003-11 |
|
| Acute allergic contact dermatitis due to para-phenylenediamine after temporary henna painting. | 2003-11 |
|
| Contact sensitization to disperse dyes in children. | 2003-10-03 |
|
| Assembly of hybrid organic-organometallic materials through mechanochemical acid-base reactions. | 2003-09-22 |
|
| Early changes in apoptosis and proliferation following primary chemotherapy for breast cancer. | 2003-09-15 |
|
| Permanent-wave dermatitis: contact allergy to cysteamine hydrochloride. | 2003-09 |
|
| Identification of aminobiphenyl derivatives in commercial hair dyes. | 2003-09 |
|
| Important role of fungal intracellular laccase for melanin synthesis: purification and characterization of an intracellular laccase from Lentinula edodes fruit bodies. | 2003-09 |
|
| The association between ambient air conditions (temperature and absolute humidity), irritant sodium lauryl sulfate patch test reactions and patch test reactivity to standard allergens. | 2003-08 |
|
| Reductive desorption of 11-mercaptoundecanoic acid monolayers modified by covalent attachment of 1,3- and 1,4-phenylenediamine. | 2003-07-15 |
|
| Fluorescent photoinduced electron transfer (PET) sensing molecules with p-phenylenediamine as electron donor. | 2003-06-27 |
|
| Rapid de-localization of actin leading edge components with BDM treatment. | 2003-06-03 |
|
| Contributions of symmetric and asymmetric normal coordinates to the intervalence electronic absorption and resonance Raman spectra of a strongly coupled p-phenylenediamine radical cation. | 2003-05-14 |
|
| High frequency of simultaneous sensitivity to Disperse Orange 3 in patients with positive patch tests to para-phenylenediamine. | 2003-05 |
|
| Preparation of N-aryl azacrown ether derivatives, using arene-iron chemistry. | 2003-03-21 |
|
| Sensitive spectrophotometric method for the determination of indomethacin in capsules. | 2003-03-10 |
|
| Immediate-type hypersensitivity and allergic contact dermatitis due to para-phenylenediamine in hair dye. | 2003-03 |
|
| Is PPD a useful screening agent? | 2003-02 |
|
| Simultaneous determination of oxidative hair dye p-phenylenediamine and its metabolites in human and rabbit biological fluids. | 2003-01-15 |
|
| Highly sensitive reaction of tryptophan with p-phenylenediamine. | 2003-01-15 |
|
| Latex hypersensitivity: relationship with positive prick test and patch test responses among hairdressers. | 2003-01 |
|
| An off-line respirometric procedure to determine inhibition and toxicity of biodegradable compounds in biomass from an industrial WWTP. | 2003 |
|
| Genotoxicity of textile dyes evaluated with Ames test and rec-assay. | 2003 |
|
| Mechanochemical assembly of hydrogen bonded organic-organometallic solid compounds. | 2002-12-21 |
|
| Childhood allergic contact dermatitis from henna tattoo. | 2002-11-20 |
|
| 55 cases of allergic reactions to hair dye: a descriptive, consumer complaint-based study. | 2002-11 |
|
| Contact hypersensitivity in hand dermatitis. | 2002-10 |
|
| Lymphomatoid allergic contact dermatitis from para-phenylenediamine. | 2002-09 |
|
| Detection and determination of aromatic amines as products of reductive splitting from selected azo dyes. | 2002-09 |
|
| Further investigation of the prohapten concept: reactions to benzene derivatives in man. | 1992-08 |
Patents
Sample Use Guides
EPA has calculated a provisional Reference Dose (RfD) of 0.19 milligrams per kilogram body weight per day (mg/kg/d) based on whole body effects in rats.
Route of Administration:
Other
To assess the protective effects of the test compound (p-Phenylenediamine), viability of HT22 cells were determined after exposure to glutamate (5 mM) and varying concentrations of test compound for 24 h. Glutamate (5 mM) reduced viability of HT22 cells to 10% or less after this time.
| Substance Class |
Chemical
Created
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admin
on
Edited
Mon Mar 31 18:11:12 GMT 2025
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Mon Mar 31 18:11:12 GMT 2025
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| Record UNII |
U770QIT64J
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| Record Status |
Validated (UNII)
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EPA PESTICIDE CODE |
600002
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NDF-RT |
N0000185508
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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106-50-3
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m8667
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PRIMARY | Merck Index | ||
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P-PHENYLENEDIAMINE
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U770QIT64J
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U770QIT64J
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SUB15001MIG
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2518
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100000078867
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203-404-7
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C029728
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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4777
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1362740
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7814
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51403
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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DTXSID9021138
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DB14141
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ACTIVE MOIETY |
