General Information

MaintermDIPHENYLAMINE
CAS Reg.No.(or other ID)122-39-4
Regnum 175.105
175.300
176.170
176.180
177.2600

From www.fda.gov

Toxicity Profile

Route of Exposure
Mechanism of ToxicityDiphenylamine uncouples mitochondrial oxidative phosphorylation, resulting in a decrease in hepatocellular ATP content and consequently hepatocyte injury . Short-term and long-term exposure in animal models results in altered haematological parameters, splenic erythropoiesis, splenic congestion and haemosiderosis .
Metabolism
Toxicity Values
Lethal Dose
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk Level
Health Effects
Treatment
Reference
  1. Jitsui Y, Ohtani N: Transmission electron microscope observation of organic-inorganic hybrid thin active layers of light-emitting diodes. Nanoscale Res Lett. 2012 Oct 25;7(1):591. doi: 10.1186/1556-276X-7-591.[23095451 ]
  2. Ramon JG, Bittner ER: Excited state calculations on fluorene-based polymer blends: effect of stacking orientation and solvation. J Chem Phys. 2007 May 14;126(18):181101.[17508783 ]
  3. Shyla B, Nagendrappa G: Redox spectrophotometric method involving electrolytically generated manganese(III) sulphate with diphenylamine for the determination of ascorbic acid present in the samples of various fruits, commercial juices and sprouted food grains. Food Chem. 2013 Jun 1;138(2-3):2036-42. doi: 10.1016/j.foodchem.2012.11.076. Epub 2012 Nov 24.[23411340 ]
  4. para-Nitrosodiphenylamine. IARC Monogr Eval Carcinog Risk Chem Hum. 1982 Apr;27:227-33.[6955265 ]
  5. Nagata T, Masuda K, Maeno S, Miura I: Synthesis and structure-activity study of fungicidal anilinopyrimidines leading to mepanipyrim (KIF-3535) as an anti-Botrytis agent. Pest Manag Sci. 2004 Apr;60(4):399-407.[15119603 ]
  6. Benson-Smith JJ, Wilson J, Dyer-Smith C, Mouri K, Yamaguchi S, Murata H, Nelson J: Long-lived exciplex formation and delayed exciton emission in bulk heterojunction blends of silole derivative and polyfluorene copolymer: the role of morphology on exciplex formation and charge separation. J Phys Chem B. 2009 Jun 4;113(22):7794-9. doi: 10.1021/jp808671f.[19435328 ]
  7. Huang YS, Westenhoff S, Avilov I, Sreearunothai P, Hodgkiss JM, Deleener C, Friend RH, Beljonne D: Electronic structures of interfacial states formed at polymeric semiconductor heterojunctions. Nat Mater. 2008 Jun;7(6):483-9. doi: 10.1038/nmat2182. Epub 2008 Apr 27.[18438413 ]
  8. Lin Y, El-Khouly ME, Chen Y, Supur M, Gu L, Li Y, Fukuzumi S: A new cyanofluorene-triphenylamine copolymer: synthesis and photoinduced intramolecular electron transfer processes. Chemistry. 2009 Oct 19;15(41):10818-24. doi: 10.1002/chem.200900752.[19760714 ]
  9. Liu B, Najari A, Pan C, Leclerc M, Xiao D, Zou Y: New low bandgap dithienylbenzothiadiazole vinylene based copolymers: synthesis and photovoltaic properties. Macromol Rapid Commun. 2010 Feb 16;31(4):391-8. doi: 10.1002/marc.200900654. Epub 2009 Nov 24.[21590919 ]
  10. Dalby O, Birkett JW: The evaluation of solid phase micro-extraction fibre types for the analysis of organic components in unburned propellant powders. J Chromatogr A. 2010 Nov 12;1217(46):7183-8. doi: 10.1016/j.chroma.2010.09.012. Epub 2010 Sep 15.[20933233 ]
  11. Fun HK, Chantrapromma S, D'Silva ED, Patil PS, Dharmaprakash SM: S-Benzyl-thiouronium 4-anilinobenzene-sulfonate. Acta Crystallogr Sect E Struct Rep Online. 2008 Aug 30;64(Pt 9):o1858-9. doi: 10.1107/S160053680802727X.[21201828 ]
  12. Hirai Y, Uozumi Y: Heterogeneous aromatic amination of aryl halides with arylamines in water with PS-PEG resin-supported palladium complexes. Chem Asian J. 2010 Aug 2;5(8):1788-95. doi: 10.1002/asia.201000192.[20572283 ]
  13. Jin R, Levermore PA, Huang J, Wang X, Bradley DD, deMello JC: On the use and influence of electron-blocking interlayers in polymer light-emitting diodes. Phys Chem Chem Phys. 2009 May 14;11(18):3455-62. doi: 10.1039/b819200f. Epub 2009 Mar 6.[19421548 ]
  14. Sedinova V, Urbanova E, Skarda J, Jukl A: [Determination of the number of somatic cells in milk using the rapid diphenylamine DNA filter method]. Vet Med (Praha). 1985 Aug;30(8):467-75.[3929447 ]
  15. Agarwala S, Peh CK, Ho GW: Investigation of ionic conductivity and long-term stability of a LiI and KI coupled diphenylamine quasi-solid-state dye-sensitized solar cell. ACS Appl Mater Interfaces. 2011 Jul;3(7):2383-91. doi: 10.1021/am200296f. Epub 2011 Jun 20.[21648469 ]
  16. Marjanovic B, Juranic I, Ciric-Marjanovic G: Revised mechanism of Boyland-Sims oxidation. J Phys Chem A. 2011 Apr 21;115(15):3536-50. doi: 10.1021/jp111129t. Epub 2011 Mar 24.[21434676 ]
  17. Kim JS, Lu L, Sreearunothai P, Seeley A, Yim KH, Petrozza A, Murphy CE, Beljonne D, Cornil J, Friend RH: Optoelectronic and charge transport properties at organic-organic semiconductor interfaces: comparison between polyfluorene-based polymer blend and copolymer. J Am Chem Soc. 2008 Oct 1;130(39):13120-31. doi: 10.1021/ja803766j. Epub 2008 Sep 4.[18767836 ]
  18. Patterson J, Mura C: Rapid colorimetric assays to qualitatively distinguish RNA and DNA in biomolecular samples. J Vis Exp. 2013 Feb 4;(72):e50225. doi: 10.3791/50225.[23407542 ]
  19. Lee KP, Gopalan AI, Kim KS, Santhosh P: Synthesis and characterization of processable multi-walled carbon nanotubes-sulfonated polydiphenylamine graft copolymers. J Nanosci Nanotechnol. 2007 Oct;7(10):3386-93.[18330145 ]
  20. Abid-Essefi S, Bouaziz C, Golli-Bennour EE, Ouanes Z, Bacha H: Comparative study of toxic effects of zearalenone and its two major metabolites alpha-zearalenol and beta-zearalenol on cultured human Caco-2 cells. J Biochem Mol Toxicol. 2009 Jul-Aug;23(4):233-43. doi: 10.1002/jbt.20284.[19705349 ]
  21. Philips MF, Gopalan AI, Lee KP: Development of a novel cyano group containing electrochemically deposited polymer film for ultrasensitive simultaneous detection of trace level cadmium and lead. J Hazard Mater. 2012 Oct 30;237-238:46-54. doi: 10.1016/j.jhazmat.2012.07.069. Epub 2012 Aug 24.[22964385 ]
  22. Masubuchi Y, Yamada S, Horie T: Possible mechanism of hepatocyte injury induced by diphenylamine and its structurally related nonsteroidal anti-inflammatory drugs. J Pharmacol Exp Ther. 2000 Mar;292(3):982-7.[10688613 ]

From T3DB


Targets

General Function:
Norepinephrine:sodium symporter activity
Specific Function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular Weight:
69331.42 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Prostaglandin e receptor activity
Specific Function:
Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(s) proteins that stimulate adenylate cyclase. The subsequent raise in intracellular cAMP is responsible for the relaxing effect of this receptor on smooth muscle.
Gene Name:
PTGER2
Uniprot ID:
P43116
Molecular Weight:
39759.945 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Type iii transforming growth factor beta receptor binding
Specific Function:
Multifunctional protein that controls proliferation, differentiation and other functions in many cell types. Many cells synthesize TGFB1 and have specific receptors for it. It positively and negatively regulates many other growth factors. It plays an important role in bone remodeling as it is a potent stimulator of osteoblastic bone formation, causing chemotaxis, proliferation and differentiation in committed osteoblasts. Can promote either T-helper 17 cells (Th17) or regulatory T-cells (Treg) lineage differentiation in a concentration-dependent manner. At high concentrations, leads to FOXP3-mediated suppression of RORC and down-regulation of IL-17 expression, favoring Treg cell development. At low concentrations in concert with IL-6 and IL-21, leads to expression of the IL-17 and IL-23 receptors, favoring differentiation to Th17 cells.
Gene Name:
TGFB1
Uniprot ID:
P01137
Molecular Weight:
44340.685 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Hydroxymethylglutaryl-coa synthase activity
Specific Function:
This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase.
Gene Name:
HMGCS2
Uniprot ID:
P54868
Molecular Weight:
56634.915 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Sulfotransferase activity
Specific Function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
Gene Name:
SULT2A1
Uniprot ID:
Q06520
Molecular Weight:
33779.57 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]

From T3DB