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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:41:37 UTC
Update Date2017-12-07 04:29:03 UTC
HMDB IDHMDB0041830
Secondary Accession Numbers
  • HMDB41830
Metabolite Identification
Common NameAtrazine
DescriptionAtrazine is an organic compound consisting of an s-triazine-ring is a widely used herbicide. Its use is controversial due to widespread contamination in drinking water and its associations with birth defects and menstrual problems when consumed by humans at concentrations below government standards. Although it has been banned in the European Union,[2] it is still one of the most widely used herbicides in the world (Wikipedia). Atrazine is a suspected teratogen, causing demasculinization in male northern leopard frog even at low concentrations, and an estrogen disruptor. A 2010 study found that atrazine rendered 75 percent of male frogs sterile and turned one in 10 into females. A 2002 study found that exposure to atrazine caused male tadpoles to turn into hermaphrodites - frogs with both male and female sexual characteristics. But another study, requested by EPA and funded by Syngenta, was unable to reproduce these results. Atrazine was banned in the European Union (EU) in 2004 because of its persistent groundwater contamination. In the United States, however, atrazine is one of the most widely used herbicides, with 76 million pounds of it applied each year, in spite of the restriction that used to be imposed. Its endocrine disruptor effects, possible carcinogenic effect, and epidemiological connection to low sperm levels in men has led several researchers to call for banning it in the US.Rates of biodegradation are affected by atrazine's low solubility, thus surfactants may increase the degradation rate. Though the two alkyl moieties readily support growth of certain microorganisms, the atrazine ring is a poor energy source due to the oxidized state of ring carbon. In fact, the most common pathway for atrazine degradation involves the intermediate, cyanuric acid, in which carbon is fully oxidized, thus the ring is primarily a nitrogen source for aerobic microorganisms. Atrazine may be catabolized as a carbon and nitrogen source in reducing environments, and some aerobic atrazine degraders have been shown to use the compound for growth under anoxia in the presence of nitrate as an electron acceptor, a process referred to as a denitrification. When atrazine is used as a nitrogen source for bacterial growth, degradation may be regulated by the presence of alternative sources of nitrogen. In pure cultures of atrazine-degrading bacteria, as well as active soil communitites, atrazine ring nitrogen, but not carbon are assimilated into microbial biomass. Low concentrations of glucose can decrease the bioavailability, whereas higher concentrations promote the catabolism of atrazine. Tyrone Hayes, Department of Integrative Biology, University of California, notes that all of the studies that failed to conclude that atrazine caused hermaphroditism were plagued by poor experimental controls and were funded by Syngenta, one of the companies that produce the chemical. The U.S. Environmental Protection Agency (EPA) and its independent Scientific Advisory Panel (SAP) examined all available studies on this topic including Hayes' work and concluded that there are 'currently insufficient data' to determine if atrazine affects amphibian development. Hayes, formerly part of the SAP panel, resigned in 2000 to continue studies independently. The EPA and its SAP made recommendations concerning proper study design needed for further investigation into this issue. As required by the EPA, Syngenta conducted two experiments under Good Laboratory Practices (GLP) and inspection by the EPA and German regulatory authorities. The paper concluded 'These studies demonstrate that long-term exposure of larval X. laevis to atrazine at concentrations ranging from 0.01 to 100 microg/l does not affect growth, larval development, or sexual differentiation.' Another independent study in 2008 determined that 'the failure of recent studies to find that atrazine feminizes X. laevis calls into question the herbicide's role in that decline.' A report written in Environmental Science and Technology (May 15, 2008) cites the independent work of researchers in Japan, who were unable to replicate Hayes' work. 'The scientists found no hermaphrodite frogs; no increase in aromatase as measured by aromatase mRNA induction; and no increase in vitellogenin, another marker of feminization.'
Structure
Thumb
Synonyms
ValueSource
2-chloro-4-(ethylamino)-6-(isopropylamino)-1,3,5-TriazineChEBI
2-chloro-4-ethylamino-6-isopropylamino-1,3,5-TriazineChEBI
2-chloro-4-ethylamino-6-isopropylamino-S-TriazineChEBI
2-chloro-4-isopropylamino-6-ethylamino-1,3,5-TRIAZINEChEBI
2-ethylamino-4-isopropylamino-6-chloro-S-TriazineChEBI
6-chloro-N-Ethyl-n'-(1-methylethyl)-1,3,5-triazine-2,4-diamineChEBI
6-chloro-N-Ethyl-n'-isopropyl-1,3,5-triazine-2,4-diamineChEBI
1-chloro-3-(ethylamino)-5-(isopropylamino)-2,4,6-TriazineHMDB
1-chloro-3-(ethylamino)-5-(isopropylamino)-S-TriazineHMDB
2-aethylamino-4-Chlor-6-isopropylamino-1,3,5-triazinHMDB
2-chloro-4-(2-propylamino)-6-(ethylamino)-S-TriazineHMDB
2-chloro-4-(ethylamino)-6-(isopropylamino)-S-TriazineHMDB
2-chloro-4-Ethylamineisopropylamine-S-triazineHMDB
2-chloro-4-isopropylamino-6-ethylamino -1,3,5-TRIAZINEHMDB
6-chloro-4-(ethylamino)-2-(isopropylamino)-S-TriazineHMDB
6-chloro-N-Ethyl-n'-(propan-2-yl)-1,3,5-triazine-2,4-diamineHMDB
AatramHMDB
AatrexHMDB
Aatrex 4lHMDB
Aatrex 4LCHMDB
Aatrex 80WHMDB
Aatrex nine-OHMDB
Actinite PKHMDB
AkticonHMDB
AktikonHMDB
Aktikon PKHMDB
Aktinit aHMDB
Aktinit PKHMDB
ArgezinHMDB
AtazinaxHMDB
AtraflowHMDB
Atraflow plusHMDB
AtranexHMDB
AtrasineHMDB
AtratafHMDB
AtratolHMDB
Atratol aHMDB
AtrazinHMDB
Atrazine 4lHMDB
Atrazine 80WHMDB
AtredHMDB
AtrexHMDB
AttrexHMDB
ATZHMDB
Azinotox 500HMDB
CandexHMDB
Cekuzina-THMDB
ChromozinHMDB
CrisaminaHMDB
CrisatrinaHMDB
CrisazineHMDB
CyazinHMDB
farmco AtrazineHMDB
FarmozineHMDB
FenaminHMDB
FenamineHMDB
FenatrolHMDB
FogardHMDB
GesaprimHMDB
Gesaprim 50HMDB
GesoprimHMDB
GriffexHMDB
Griffex 4lHMDB
HerbatoxolHMDB
HungazinHMDB
Hungazin PKHMDB
InakorHMDB
LaddockHMDB
MaizinaHMDB
MebazineHMDB
OleogesaprimHMDB
PitezinHMDB
PrimatolHMDB
Primatol aHMDB
PrimazeHMDB
PrimoleoHMDB
RadazinHMDB
Radazin THMDB
RadizinHMDB
RadizineHMDB
StrazineHMDB
Triazine a 1294HMDB
VectalHMDB
Vectal SCHMDB
Weedex aHMDB
WonukHMDB
ZeaphosHMDB
ZeaposHMDB
ZeazinHMDB
ZeazineHMDB
ZeoposHMDB
GesamprimMeSH
Chemical FormulaC8H14ClN5
Average Molecular Weight215.683
Monoisotopic Molecular Weight215.09377318
IUPAC Name6-chloro-N2-ethyl-N4-(propan-2-yl)-1,3,5-triazine-2,4-diamine
Traditional Nameatrazine
CAS Registry Number1912-24-9
SMILES
CCNC1=NC(Cl)=NC(NC(C)C)=N1
InChI Identifier
InChI=1S/C8H14ClN5/c1-4-10-7-12-6(9)13-8(14-7)11-5(2)3/h5H,4H2,1-3H3,(H2,10,11,12,13,14)
InChI KeyMXWJVTOOROXGIU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chloro-s-triazines. These are aromatic compounds containing a 1,3,5-triazine ring that is substituted at the 2-position with a chlorine atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazines
Sub Class1,3,5-triazines
Direct ParentChloro-s-triazines
Alternative Parents
Substituents
  • Chloro-s-triazine
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Role

Environmental role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point173 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.035 mg/mL at 26 °CNot Available
LogP2.61Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP2.7ALOGPS
logP2.2ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)14.48ChemAxon
pKa (Strongest Basic)3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area62.73 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.22 m³·mol⁻¹ChemAxon
Polarizability22.58 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uxr-6690000000-583f3e9640ef44c789ceView in MoNA
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-0uxu-9650000000-8ed90c24a7dac8c0763fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uxr-6690000000-583f3e9640ef44c789ceView in MoNA
GC-MSGC-MS Spectrum - GC-EI-Q (Non-derivatized)splash10-0uxu-9650000000-8ed90c24a7dac8c0763fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4930000000-a800c662430d89a999bfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0090000000-1f8dc1708e21447c72a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00xr-0950000000-698ba6253f9249ac28daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-f20aaabd2097e4fd3d64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-007k-0900000000-5b2179fcabb41a9319e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000t-0900000000-bb61e6f57dde5f72c357View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-b333a1dd57dddfe03e6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-066208bd5cb9497fe53eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0190000000-dadd355493b3a581e39cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00xr-0960000000-1af13a0d4df29165659fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-2900000000-37f6b1aa187e630690dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0g4j-6900000000-b43d1386f51d229ee0f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0uxs-9700000000-2523140d0327bff497ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-066208bd5cb9497fe53eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0190000000-ad3a817f71f2c0654dd8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00xr-1960000000-6cd3e48811e8b25a7c65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-2900000000-99e6afb84401fc17d138View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0g4j-5900000000-d4992767b3b313839a0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0uxs-9800000000-eed7a36ca3c28d5cead3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0900000000-e72e1e890a493331145dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0690000000-729ca7a9ad2de01cfe64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1910000000-0146c181e5d03eb2b37eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h37-9600000000-7de90ffbda7ec9663fbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3910000000-e195d0c31e12e3e7a831View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06rj-7920000000-d4fc9069fd78b8033e88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-7900000000-000a24131372a074e030View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0uxr-8890000000-b28a10166e9ef8427050View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07392
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2169
KEGG Compound IDC06551
BioCyc IDATRAZINE
BiGG IDNot Available
Wikipedia LinkAtrazine
METLIN IDNot Available
PubChem Compound2256
PDB IDATZ
ChEBI ID15930
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available