Benzidine
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Basic Info
| Common Name | Benzidine(F03288) |
| 2D Structure | |
| Description | Benzidine is the organic compound with the formula (C6H4NH2)2. it is an aromatic amine. It is prepared in a two step process from nitrobenzene. First, the nitrobenzene is converted to 1,2-diphenylhydrazine, usually using iron powder as the reducing agent. Treatment of this hydrazine with mineral acids induces a rearrangement reaction to 4,4'-benzidine. Smaller amounts of other isomers are also formed. The benzidine rearrangement, which proceeds intramolecularly, is a classic mechanistic puzzle in organic chemistry. This aromatic amine is a component of a test for cyanide and also in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer. Since August 2010 benzidine dyes are included in the EPA's List of Chemicals of Concern. |
| FRCD ID | F03288 |
| CAS Number | 92-87-5 |
| PubChem CID | 7111 |
| Formula | C12H12N2 |
| IUPAC Name | 4-(4-aminophenyl)aniline |
| InChI Key | HFACYLZERDEVSX-UHFFFAOYSA-N |
| InChI | InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2 |
| Canonical SMILES | C1=CC(=CC=C1C2=CC=C(C=C2)N)N |
| Isomeric SMILES | C1=CC(=CC=C1C2=CC=C(C=C2)N)N |
| Wikipedia | Benzidine |
| Synonyms |
BENZIDINE
92-87-5
4,4'-Diaminobiphenyl
p-Diaminodiphenyl
4,4'-Bianiline
biphenyl-4,4'-diamine
4,4'-Biphenylenediamine
[1,1'-Biphenyl]-4,4'-diamine
4,4'-Biphenyldiamine
4,4'-Diaminodiphenyl
|
| Classifies |
Pollutant
|
| Update Date | Nov 13, 2018 17:07 |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 184.242 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 1 |
| Complexity | 145 |
| Monoisotopic Mass | 184.1 |
| Exact Mass | 184.1 |
| XLogP | 1.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 14 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9397 |
| Human Intestinal Absorption | HIA+ | 0.9860 |
| Caco-2 Permeability | Caco2+ | 0.7586 |
| P-glycoprotein Substrate | Non-substrate | 0.8042 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9530 |
| Non-inhibitor | 0.8856 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8576 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.4524 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8406 |
| CYP450 2D6 Substrate | Non-substrate | 0.8914 |
| CYP450 3A4 Substrate | Non-substrate | 0.7989 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.7308 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8428 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9322 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8028 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.7221 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.8486 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9855 |
| Non-inhibitor | 0.8137 | |
| AMES Toxicity | AMES toxic | 0.9239 |
| Carcinogens | Carcinogens | 0.6722 |
| Fish Toxicity | High FHMT | 0.9201 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9864 |
| Honey Bee Toxicity | Low HBT | 0.7661 |
| Biodegradation | Not ready biodegradable | 0.9780 |
| Acute Oral Toxicity | II | 0.7774 |
| Carcinogenicity (Three-class) | Danger | 0.5280 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.6373 | LogS |
| Caco-2 Permeability | 1.4932 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.7436 | LD50, mol/kg |
| Fish Toxicity | 1.1653 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9587 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Congo red dye affects survival and reproduction in the cladoceran Ceriodaphnia dubia. Effects of direct and dietary exposure. | Ecotoxicology | 2016 Dec | 27670667 |
| A low-cost wheat bran medium for biodegradation of the benzidine-based carcinogenic dye Trypan Blue using a microbial consortium. | Int J Environ Res Public Health | 2015 Mar 25 | 25815522 |
| [Experimental study of the effect of benzidinsulfon, included in the group of diaminodifenils, with potential carcinogenic effects]. | Vopr Onkol | 2014 | 24772622 |
| Bladder cancer, a review of the environmental risk factors. | Environ Health | 2012 Jun 28 | 22759493 |
| Toxicology of food dyes. | Int J Occup Environ Health | 2012 Jul-Sep | 23026007 |
| Cloud point extraction and determination of trace trichlorfon by high performanceliquid chromatography with ultraviolet-detection based on its catalytic effect onbenzidine oxidizing. | Anal Chim Acta | 2008 Apr 28 | 18405681 |
| Iron deposit state and risk factors for anemia in the elderly. | Acta Med Indones | 2005 Jul-Sep | 16138416 |
| Chemical and enzymatic interactions of Direct Black 38 and Direct Brown 1 on release of carcinogenic amines. | Chemosphere | 2004 Sep | 15261529 |
| How many food additives are rodent carcinogens? | Environ Mol Mutagen | 2002 | 11813298 |
| Determination of benzidine in the food colours tartrazine and sunset yellow FCF, by reduction and derivatization followed by high-performance liquidchromatography. | Food Addit Contam | 1999 Sep | 10755129 |
| Alterations in epidermal growth factor binding to hepatic membranes following dietary exposure of rats to known hepatocarcinogens. | Toxicol Lett | 1997 Mar 14 | 9096280 |
| Determination of combined benzidine in FD&C Yellow No. 6 (Sunset Yellow FCF). | Food Chem Toxicol | 1995 Oct | 7590527 |
| Determination of combined benzidine in FD & C yellow no. 5 (tartrazine), using a highly sensitive analytical method. | Food Chem Toxicol | 1993 Oct | 8225134 |
| Chemical reduction of FD&C yellow No. 5 to determine combined benzidine. | J Chromatogr | 1993 Apr 9 | 8491830 |
| Cloning and expression of the Clostridium thermosulfurogenes glucose isomerasegene in Escherichia coli and Bacillus subtilis. | Appl Environ Microbiol | 1990 Sep | 2125812 |
| The colorimetric determination of cyanide in human food and animal feed. | Z Lebensm Unters Forsch | 1985 Nov | 4072427 |
| [Hygienic significance of patulin in foods. 1. Analytical detection of patulin]. | Nahrung | 1979 | 471032 |
| [Chlor-benzidine - a thin layer chromatographic agent for detection of patulin in apple juice]. | Nahrung | 1977 | 854081 |
| Serological studies of types A, B, and E botulinal toxins by passive hemagglutination and bentonite flocculation. | J Bacteriol | 1966 Mar | 5326104 |
Targets
- General Function:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.
- Gene Name:
- HBD
- Uniprot ID:
- P02042
- Molecular Weight:
- 16055.41 Da
- Mechanism of Action:
- Benzidine has been shown to bind hemoglobin.
References
- Birner G, Albrecht W, Neumann HG: Biomonitoring of aromatic amines. III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol. 1990;64(2):97-102. [2350241 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- The epsilon chain is a beta-type chain of early mammalian embryonic hemoglobin.
- Gene Name:
- HBE1
- Uniprot ID:
- P02100
- Molecular Weight:
- 16202.71 Da
- Mechanism of Action:
- Benzidine has been shown to bind hemoglobin.
References
- Birner G, Albrecht W, Neumann HG: Biomonitoring of aromatic amines. III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol. 1990;64(2):97-102. [2350241 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
- Gene Name:
- HBG1
- Uniprot ID:
- P69891
- Molecular Weight:
- 16140.37 Da
- Mechanism of Action:
- Benzidine has been shown to bind hemoglobin.
References
- Birner G, Albrecht W, Neumann HG: Biomonitoring of aromatic amines. III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol. 1990;64(2):97-102. [2350241 ]
- General Function:
- Gamma chains make up the fetal hemoglobin F, in combination with alpha chains.
- Specific Function:
- Heme binding
- Gene Name:
- HBG2
- Uniprot ID:
- P69892
- Molecular Weight:
- 16126.35 Da
- Mechanism of Action:
- Benzidine has been shown to bind hemoglobin.
References
- Birner G, Albrecht W, Neumann HG: Biomonitoring of aromatic amines. III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol. 1990;64(2):97-102. [2350241 ]
- General Function:
- Oxygen transporter activity
- Gene Name:
- HBM
- Uniprot ID:
- Q6B0K9
- Molecular Weight:
- 15617.97 Da
- Mechanism of Action:
- Benzidine has been shown to bind hemoglobin.
References
- Birner G, Albrecht W, Neumann HG: Biomonitoring of aromatic amines. III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol. 1990;64(2):97-102. [2350241 ]
- General Function:
- Oxygen transporter activity
- Gene Name:
- HBQ1
- Uniprot ID:
- P09105
- Molecular Weight:
- 15507.575 Da
- Mechanism of Action:
- Benzidine has been shown to bind hemoglobin.
References
- Birner G, Albrecht W, Neumann HG: Biomonitoring of aromatic amines. III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol. 1990;64(2):97-102. [2350241 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- The zeta chain is an alpha-type chain of mammalian embryonic hemoglobin.
- Gene Name:
- HBZ
- Uniprot ID:
- P02008
- Molecular Weight:
- 15636.845 Da
- Mechanism of Action:
- Benzidine has been shown to bind hemoglobin.
References
- Birner G, Albrecht W, Neumann HG: Biomonitoring of aromatic amines. III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol. 1990;64(2):97-102. [2350241 ]
- 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 Da
References
- 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:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- 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:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.
- Gene Name:
- HBA1
- Uniprot ID:
- P69905
- Molecular Weight:
- 15257.405 Da
- Mechanism of Action:
- Benzidine has been shown to bind hemoglobin.
References
- Birner G, Albrecht W, Neumann HG: Biomonitoring of aromatic amines. III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol. 1990;64(2):97-102. [2350241 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
- Gene Name:
- HBB
- Uniprot ID:
- P68871
- Molecular Weight:
- 15998.34 Da
- Mechanism of Action:
- Benzidine has been shown to bind hemoglobin.
References
- Birner G, Albrecht W, Neumann HG: Biomonitoring of aromatic amines. III: Hemoglobin binding of benzidine and some benzidine congeners. Arch Toxicol. 1990;64(2):97-102. [2350241 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
References
- 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 ]