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Record Information
Version2.0
Creation Date2009-03-06 18:58:03 UTC
Update Date2014-12-24 20:21:04 UTC
Accession NumberT3D0084
Identification
Common NameHydrazine
ClassSmall Molecule
DescriptionBeing bifunctional, with two amines, hydrazine is a key building block for the preparation of many heterocyclic compounds via condensation with a range of difunctional electrophiles. With 2,4-pentanedione, it condenses to give the 3,5-dimethylpyrazole. In the Einhorn-Brunner reaction hydrazines react with imides to give triazoles. Hydrazine is a convenient reductant because the by-products are typically nitrogen gas and water. Thus, it is used as an antioxidant, an oxygen scavenger, and a corrosion inhibitor in water boilers and heating systems. It is also used to reduce metal salts and oxides to the pure metals in electroless nickel plating and plutonium extraction from nuclear reactor waste. Hydrazine is an inorganic chemical compound with the formula N2H4. It is a colourless liquid with an ammonia-like odor and is derived from the same industrial chemistry processes that manufacture ammonia. However, hydrazine has physical properties that are more similar to those of water. The propanone azine is an intermediate in the Atofina-PCUK synthesis. Direct alkylation of hydrazines with alkyl halides in the presence of base affords alkyl-substituted hydrazines, but the reaction is typically inefficient due to poor control on level of substitution (same as in ordinary amines). The reduction of hydrazones to hydrazines present a clean way to produce 1,1-dialkylated hydrazines.
Compound Type
  • Cigarette Toxin
  • Food Toxin
  • Hydrazine
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Inorganic Compound
  • Metabolite
  • Non-Metal
  • Organic Compound
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Amerzine
Catalyzed hydrazine
Diamide
Diamine
Diazane
HDZ
Hydrazin
Hydrazine (anhydrous)
Hydrazine base
Hydrazine solution
Hydrazines
Levoxine
Nitrogen hydride
Oxytreat 35
Scav-ox II
Zerox
Chemical FormulaH4N2
Average Molecular Mass32.045 g/mol
Monoisotopic Mass32.037 g/mol
CAS Registry Number302-01-2
IUPAC Namehydrazine
Traditional Namehydrazine
SMILESNN
InChI IdentifierInChI=1S/H4N2/c1-2/h1-2H2
InChI KeyInChIKey=OAKJQQAXSVQMHS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of inorganic compounds known as homogeneous other non-metal compounds. These are inorganic non-metallic compounds in which the largest atom belongs to the class of 'other non-metals'.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassHomogeneous other non-metal compounds
Sub ClassNot Available
Direct ParentHomogeneous other non-metal compounds
Alternative Parents
Substituents
  • Homogeneous other non metal
  • Hydrazine derivative
Molecular FrameworkNot Available
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point2°C
Boiling PointNot Available
Solubility1000 mg/mL
LogP-2.07
Predicted Properties
PropertyValueSource
logP-1ChemAxon
pKa (Strongest Basic)5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.04 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity10.57 m³·mol⁻¹ChemAxon
Polarizability3.25 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-7e6c9f4fe38a72218c48JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-401f7c59e214d2145c6bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-401f7c59e214d2145c6bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-401f7c59e214d2145c6bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-d34c4424b02bfa4ea545JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-d34c4424b02bfa4ea545JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-d34c4424b02bfa4ea545JSpectraViewer
Toxicity Profile
Route of ExposureOral (5); inhalation (5) ; dermal (5)
Mechanism of ToxicityAt least two mechanisms of action have been observed. One involves the direct binding of those hydrazines with a free amino group (hydrazine and 1,1-dimethylhydrazine) to key cellular molecules. Hydrazine reacts with alpha-keto acids such as vitamin B6 to form hydrazoines compounds. By binding to keto acids and forming hydrazones, hydrazine inhibits oxygen consumption with mitochondrial substrates in vitro. A second mechanism involves the generation of reactive species such as free radical intermediates or methyldiazonium ions as a result of metabolism. (6)
MetabolismHydrazines are likely to be more rapidly absorbed into the blood after ingestion or exposure to the skin than after inhalation. Once in the blood, they are probably carried to all the tissues of the body. Soon after exposure, the levels of hydrazines in the tissues fall since they are metabolised in several products such as acetyl-, diacetylhydrazine, pyruvate hydrazone, urea, and acyclic compound (1,4,5,6-tetrahydro-6-oxo-3-pyridazine carboxylic acid). However, these metabolites interacts with some important proteins and might be harmful to the body. Some studies showed that metabolites and unchanged hydrazine leave the body within one day. Small amounts can also be found in the expired air. (6, 1)
Toxicity ValuesLD50: 60 mg/kg (Oral, Rat) LD50: 91 mg/kg (Dermal, Rabbit) LC50: 570 ppm over 4 hours (Inhalation, Rat) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (3)
Uses/SourcesHydrazine is mainly used as a foaming agent in preparing polymer foams, but significant applications also include its uses as a precursor to polymerization catalysts and pharmaceuticals. Additionally, hydrazine is used in various rocket fuels and to prepare the gas precursors used in air bags. Exposure may occur from breathing contaminated air in or near a facility that makes, processes, or uses hydrazines, eating fish contaminated with hydrazines, drinking or swimming in water that has been contaminated with hydrazines, or touching soil contaminated with hydrazines, such as near some military bases or hazardous waste sites. Breathing cigarette smoke indirectly or using tobacco products may expose to small amounts of hydrazine or 1,1-dimethylhydrazine. (6)
Minimum Risk LevelIntermediate Inhalation: 0.004 ppm (2)
Health EffectsBreathing hydrazines for short periods may cause coughing and irritation of the throat and lungs, convulsions, tremors, or seizures. Breathing hydrazines for long periods may cause liver and kidney damage, as well as serious effects on reproductive organs. Eating or drinking small amounts of hydrazines may cause nausea, vomiting, uncontrolled shaking, inflammation of the nerves, drowsiness, or coma. (6)
SymptomsHydrazine may cause corrosive burning sensations, confusion, convulsions, abdominal cramps, headache, unconsciousness, vomiting, weakness, shortness of breath, or sore throat and cough, depending on the route of exposure. (5)
TreatmentInduced emesis, gastric lavage, use of saline cathartics, or activated charcoal are commonly used to decrease the gastrointestinal absorption of hydrazines. In general, these treatments are most effective when used within a few hours after oral exposure. Following dermal or ocular exposures to hydrazines, all contaminated clothing should be removed, and contacted skin should be washed immediately with soap and water. Eyes that have come in contact with hydrazines should be flushed with copious amounts of water. Contact lenses should be removed prior to flushing with water. (6)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB12973
PubChem Compound ID9321
ChEMBL IDCHEMBL1237174
ChemSpider ID8960
KEGG IDC05361
UniProt IDNot Available
OMIM ID
ChEBI ID15571
BioCyc ID4-HYDROXYMETHYLPHENYLHYDRAZINE
CTD IDC029424
Stitch IDHydrazine
PDB IDNot Available
ACToR ID713
Wikipedia Linkhydrazine
References
Synthesis ReferenceNot Available
MSDSLink
General References
  1. Sanins SM, Timbrell JA, Elcombe C, Nicholson JK: Proton NMR spectroscopic studies on the metabolism and biochemical effects of hydrazine in vivo. Arch Toxicol. 1992;66(7):489-95. [1332653 ]
  2. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  3. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  4. Wikipedia. Hydrazine. Last Updated 1 June 2009. [Link]
  5. International Programme on Chemical Safety (IPCS) INCHEM (1995). International Chemical Safety Card for Hydrazine. [Link]
  6. ATSDR - Agency for Toxic Substances and Disease Registry (1997). Toxicological profile for hydrazine. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  7. The Physical and Theoretical Chemistry Laboratory of Oxford University (2008). Material Safety Data Sheet (MSDS) for hydrazine (anhydrous). [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available