Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H8N2.ClH |
Molecular Weight | 144.602 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NNC1=CC=CC=C1
InChI
InChIKey=JOVOSQBPPZZESK-UHFFFAOYSA-N
InChI=1S/C6H8N2.ClH/c7-8-6-4-2-1-3-5-6;/h1-5,8H,7H2;1H
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/19277535Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26717206 | https://www.ncbi.nlm.nih.gov/pubmed/6732840
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19277535
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26717206 | https://www.ncbi.nlm.nih.gov/pubmed/6732840
Phenylhydrazine (also known as the hydrazinobenzene) is an industrial substance suspect of carcinogenic potential for humans. Phenylhydrazine was the first hydrazine derivative characterized, reported by Emil Fischer in 1875. Phenyl-hydrazine is used to prepare indoles via the Fischer Indole Synthesis, which are intermediates in the synthesis of various dyes and pharmaceuticals. This molecule is also used to induce acute hemolytic anemia in animal models. Exposure to phenylhydrazine may cause contact dermatitis, hemolytic anemia, and liver damage.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26717206 |
230.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Oxidative stress, glucose-6-phosphate dehydrogenase and the red cell. | 2001 |
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Effects of ageing and increased haemolysis on the levels of dolichol in rat spleen. | 2001 Dec |
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Characterization of the iron transporter DMT1 (NRAMP2/DCT1) in red blood cells of normal and anemic mk/mk mice. | 2001 Dec 15 |
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Traceless, self-cleaving solid- and solution-phase parallel synthesis of 3,4,7-trisubstituted 3,4-dihydroquinoxalin-2-ones. | 2001 Nov-Dec |
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Induced synthesis of albumin-like protein in damaged rat reticulocytes. | 2001 Oct |
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The role of thyroid hormone on phenylhydrazine hydrochloride mediated inhibitory effects on blood acetylcholinesterase: an in vivo and in vitro study. | 2002 |
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[Signal transduction in hematopoiesis: a functional role of Stat 1 and Stat 3 in erythropoiesis and megakaryopoiesis]. | 2002 Apr |
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Towards the development of selective amine oxidase inhibitors. Mechanism-based inhibition of six copper containing amine oxidases. | 2002 Aug |
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Low iron state is associated with reduced tumor promotion in a two-stage mouse skin carcinogenesis model. | 2002 Aug |
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Design, synthesis and biological activity of YM-60828 derivatives: potent and orally-bioavailable factor Xa inhibitors based on naphthoanilide and naphthalensulfonanilide templates. | 2002 Aug |
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Use of methyl malondialdehyde as an internal standard for malondialdehyde detection: validation by isotope-dilution gas chromatography-mass spectrometry. | 2002 Dec |
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Analysis of heme oxygenase isomers in rat. | 2002 Dec |
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The ability of neonatal and maternal erythrocytes to produce reactive oxygen species in response to oxidative stress. | 2002 Feb |
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1,5-Hydride shift in Wolff-Kishner reduction of (20R)-3beta,20, 26-trihydroxy-27-norcholest-5-en-22-one: synthetic, quantum chemical, and NMR studies. | 2002 Jan |
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Membrane heme as a host factor in reducing effectiveness of dihydroartemisinin. | 2002 Jul 1 |
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[The immunometaboic effects of benfotiamine and riboxine on hemolytic anemia]. | 2002 Jul-Aug |
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Synthesis, structural characterization and antimicrobial studies of hydrazone derivatives of 3-hydroxyimino-5-methyl-2-hexanone. | 2002 Jul-Aug |
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Human kidney diamine oxidase: heterologous expression, purification, and characterization. | 2002 Jun |
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Evaluation of antioxidant properties of root bark of Hemidesmus indicus R. Br. (Anantmul). | 2002 Mar |
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Reaction of malondialdehyde-DNA adducts with hydrazines-development of a facile assay for quantification of malondialdehyde equivalents in DNA. | 2002 Mar |
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Erythropoietin restores the antitumor effectiveness of photodynamic therapy in mice with chemotherapy-induced anemia. | 2002 May |
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Expression of the two mRNA isoforms of the iron transporter Nramp2/DMTI in mice and function of the iron responsive element. | 2002 May 1 |
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[Immune and metabolic effects of carnitine and biotin in hemolytic anemia]. | 2002 May-Jun |
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Stability of agaritine - a natural toxicant of Agaricus mushrooms. | 2002 Nov |
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Mutation of alphaPhe55 of methylamine dehydrogenase alters the reorganization energy and electronic coupling for its electron transfer reaction with amicyanin. | 2002 Nov 26 |
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The gene encoding the iron regulatory peptide hepcidin is regulated by anemia, hypoxia, and inflammation. | 2002 Oct |
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Influence of hypoxia and of hypoxemia on the development of cardiac activity in zebrafish larvae. | 2002 Oct |
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Revisiting the Ullmann-ether reaction: a concise and amenable synthesis of novel dibenzoxepino[4,5-d]pyrazoles by intramolecular etheration of 4,5-(o,o'-halohydroxy)arylpyrazoles. | 2002 Oct 18 |
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Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis. | 2002 Oct 4 |
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C-C bond formation via C-H bond activation: synthesis of the core of teleocidin B4. | 2002 Oct 9 |
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Influence of storage and household processing on the agaritine content of the cultivated Agaricus mushroom. | 2002 Sep |
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Haemoglobin biosynthesis site in rabbit embryo erythroid cells. | 2003 |
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[Metabolism of heme and hemeproteins and some indices of the antioxidant system in rat erythrocytes and tissues under anemia caused by phenylhydrazine]. | 2003 |
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The microrheological changes in the course of erythrocyte senescence after phenylhydrazine injection. | 2003 |
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Inhibition of six copper-containing amine oxidases by the antidepressant drug tranylcypromine. | 2003 Apr 11 |
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Hematopoietic capacity of connexin43 wild-type and knock-out fetal liver cells not different on wild-type stroma. | 2003 Apr 15 |
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Labelling saccharides with phenylhydrazine for electrospray and matrix-assisted laser desorption-ionization mass spectrometry. | 2003 Aug 5 |
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Saturation transfer in human red blood cells with normal and unstable hemoglobin. | 2003 Feb |
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Optosensing behavior of the first Ru(II)-compound of di-2-pyridylketone-p-nitrophenylhydrazone (dpknph), [Ru(bpy)2(dpknph)]Cl2. | 2003 Jul |
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Synthesis of new chiral 2,2'-bipyridine ligands and their application in copper-catalyzed asymmetric allylic oxidation and cyclopropanation. | 2003 Jun 13 |
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Formation of meso, N-diphenylprotoporphyrin IX by an aerobic reaction of phenylhydrazine with oxyhemoglobins. | 2003 Oct |
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Amperometric and spectrophotometric determination of carbaryl in natural waters and commercial formulations. | 2003 Sep |
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An NMR and X-ray study of the structure of the azo coupling product of 4-dimethylaminopent-3-en-2-one and benzenediazonium-tetrafluoroborate. | 2003 Sep 21 |
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Tandem hydroformylation/Fischer indole synthesis: a novel and convenient approach to indoles from olefins. | 2003 Sep 4 |
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A sulfido-bridged diiron(II) compound and its reactions with nitrogenase-relevant substrates. | 2004 Apr 14 |
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Synthesis and characterization of zinc sensors based on a monosubstituted fluorescein platform. | 2004 Apr 19 |
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Matrix-assisted laser desorption/ionization tandem mass spectrometry and post-source decay fragmentation study of phenylhydrazones of N-linked oligosaccharides from ovalbumin. | 2004 May |
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Erythroid cells in immunoregulation: characterization of a novel suppressor factor. | 2004 May 15 |
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Kinetics and mechanism of the nucleophilic displacement reactions of chloroacetanilide herbicides: investigation of alpha-substituent effects. | 2004 May 19 |
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Significant differences in biological parameters between prodrugs cleavable by carboxypeptidase G2 that generate 3,5-difluoro-phenol and -aniline nitrogen mustards in gene-directed enzyme prodrug therapy systems. | 2004 May 6 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10753835
In experimental mice, phenylhydrazine (PHZ; 60 mg/kg body weight; Sigma Chem, St. Louis, MO) was injected intraperitoneally for 2 consecutive days.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6732840
Blood was drawn from healthy donors using 3.13% sodium citrate as the anticoagulant (1: 5, v/v). Cells were isolated using isoosmotic phosphate-buffered saline (PBS, pH 7,4), microcrystalline cellulose and Lu-cellulose (1: 1, w/w) as described by Beutler et al. Red blood cells were suspended in PBS and preincubated in glass test-tubes in a shaking water bath for 1 hr at 37C, after which haematocrit was adjusted to 2.5% by adding PBS. Samples containing hemoglobin were adjusted to 8 mg/ml hemoglobin in PBS, i.e. a concentration comparable to that used in experiments with red cells. Varying amounts of phenylhydrazine, ranging from 0.5 to 50 mM were added to the red blood cell or hemoglobin samples. Then 3 ml of each sample was aliquoted into 10 ml headspace vials, and the vials were immediately sealed with special air-tight rubber septums. Headspaces were flushed with hydrocarbon-free synthetic air for 2 min in order to replace laboratory air containing small amounts of hydrocarbons. The sealed samples were then incubated in a shaking water bath at 37C. After certain periods, 1 ml of the gas phase was drawn with a gas-tight syringe and injected into the gas chromatograph.
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136540
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200-444-7
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59-88-1
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m8674
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60962
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5710
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DTXSID3021148
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD