Atrazine-desethyl (CHEM008162)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:39:47 UTC
Update Date2016-10-28 10:04:30 UTC
Accession NumberCHEM008162
Identification
Common NameAtrazine-desethyl
ClassSmall Molecule
DescriptionA chloro-1,3,5-triazine that is 6-chloro-1,3,5-triazine-2,4-diamine in which one of the hydrogens of the amino group is replaced by a propan-2-yl group.
Contaminant Sources
  • FooDB Chemicals
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds
  • Suspected Compounds – Schymanski Project
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-4-chloro-6-(isopropylamino)-S-triazineChEBI
2-Chloro-4-amino-6-(isopropylamino)-S-triazineChEBI
4-DeethylatrazineChEBI
6-Chloro-N-isopropyl-1,3,5-triazine-2,4-diamineChEBI
DeethylatrazinChEBI
Desethyl atrazineChEBI
2-amino-4-chloro-6-(isopropylamino)-1,3,5-TriazineHMDB
2-amino-4-chloro-6-isopropylamino-1,3,5-TriazineHMDB
2-amino-4-isopropylamino-6-chloro-S-TriazineHMDB
2-chloro-4-amino-6-isopropylamino-S-TriazineHMDB
2-chloro-4-isopropylamino-6-amino-S-TriazineHMDB
6-chloro-N-(1-Methylethyl)-1,3,5-triazine-2,4-diamine, 9ciHMDB
6-chloro-N-(Propan-2-yl)-1,3,5-triazine-2,4-diamineHMDB
Atrazine desethylHMDB
Atrazine m (des-ethyl)HMDB
Atrazine-desethylHMDB
CIATHMDB
DeethyatrazineHMDB
DeethylatrazineHMDB
Des-ethyl atrazineHMDB
Desethyl-atrazineHMDB
DesethylatrazineHMDB
Desisopropyl propazineHMDB
2-CIATMeSH, HMDB
6-Chloro-N-(1-methylethyl)-1,3,5-triazine-2,4-diamineChEBI
Chemical FormulaC6H10ClN5
Average Molecular Mass187.630 g/mol
Monoisotopic Mass187.062 g/mol
CAS Registry Number6190-65-4
IUPAC Name6-chloro-N2-(propan-2-yl)-1,3,5-triazine-2,4-diamine
Traditional Namedesethylatrazine
SMILESCC(C)NC1=NC(N)=NC(Cl)=N1
InChI IdentifierInChI=1S/C6H10ClN5/c1-3(2)9-6-11-4(7)10-5(8)12-6/h3H,1-2H3,(H3,8,9,10,11,12)
InChI KeyDFWFIQKMSFGDCQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,3,5-triazine-2,4-diamines. These are aromatic compounds containing a 1,3,5-triazine ring which is 2,4-disusbtituted wit amine groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTriazines
Sub ClassAminotriazines
Direct Parent1,3,5-triazine-2,4-diamines
Alternative Parents
Substituents
  • 2,4-diamine-s-triazine
  • Chloro-s-triazine
  • Halo-s-triazine
  • Secondary aliphatic/aromatic amine
  • N-aliphatic s-triazine
  • Aryl chloride
  • Aryl halide
  • 1,3,5-triazine
  • Heteroaromatic compound
  • Azacycle
  • Secondary amine
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP1.5ALOGPS
logP1.54ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)3.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.72 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity51.97 m³·mol⁻¹ChemAxon
Polarizability18.29 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dv-3900000000-97171d45abd08d1a876bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-a10e57f26b5da207d59eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-29da628c248e20134739Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-2e878924f07af412fe05Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-dbfa7d338ff24901a6b5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-dd3f9784a7c2f80c135dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-33467dd77dc04d00d92aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-31358f7bbca666070739Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000j-0900000000-8e924227cb10c3fcad3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-1900000000-29f6efe3081359b4e4a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-3900000000-c3b65d177ae8ddb1e082Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0v01-6900000000-32caa26c637e0192e9d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-d6d8f3c113e2efdb5217Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-f84cd9e77492f49cddebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000j-0900000000-a1e150d527eb85f822deSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-1900000000-7c82d8c174a2f4a83036Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-3900000000-a434dfae34b0098b51b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0v01-6900000000-e67f8e31b224c6d852f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-51b22d4d60f3abf48532Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-2290849e684fc9795eceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-2288219c30d78e285c22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1900000000-02c2f6e43828e21115c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9200000000-d391a363aa3433451abeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-d500dcbf4d09b6eb1174Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-7900000000-9db2cb0a8f4f012357a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ktf-8900000000-c9bf1eba1347ea112565Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
StatusValueUnitSample LocationReference
DrugBank IDNot Available
HMDB IDHMDB0033249
FooDB IDFDB011269
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-801
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID21157
ChEBI ID28212
PubChem Compound ID22563
Kegg Compound IDC06559
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11476505
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15506812
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25281136
4. Schulte-Oehlmann U, Oehlmann J, Keil F: Before the curtain falls: endocrine-active pesticides--a German contamination legacy. Rev Environ Contam Toxicol. 2011;213:137-59. doi: 10.1007/978-1-4419-9860-6_5.
5. Schotthoefer AM, Rohr JR, Cole RA, Koehler AV, Johnson CM, Johnson LB, Beasley VR: Effects of wetland vs. landscape variables on parasite communities of Rana pipiens: links to anthropogenic factors. Ecol Appl. 2011 Jun;21(4):1257-71.
6. Sichel C, Garcia C, Andre K: Feasibility studies: UV/chlorine advanced oxidation treatment for the removal of emerging contaminants. Water Res. 2011 Dec 1;45(19):6371-80. doi: 10.1016/j.watres.2011.09.025. Epub 2011 Sep 22.
7. Lin Z, Fisher JW, Ross MK, Filipov NM: A physiologically based pharmacokinetic model for atrazine and its main metabolites in the adult male C57BL/6 mouse. Toxicol Appl Pharmacol. 2011 Feb 15;251(1):16-31. doi: 10.1016/j.taap.2010.11.009. Epub 2010 Nov 20.
8. Caquet T, Roucaute M, Mazzella N, Delmas F, Madigou C, Farcy E, Burgeot T, Allenou JP, Gabellec R: Risk assessment of herbicides and booster biocides along estuarine continuums in the Bay of Vilaine area (Brittany, France). Environ Sci Pollut Res Int. 2013 Feb;20(2):651-66. doi: 10.1007/s11356-012-1171-y. Epub 2012 Sep 16.
9. Reh R, Licha T, Geyer T, Nodler K, Sauter M: Occurrence and spatial distribution of organic micro-pollutants in a complex hydrogeological karst system during low flow and high flow periods, results of a two-year study. Sci Total Environ. 2013 Jan 15;443:438-45. doi: 10.1016/j.scitotenv.2012.11.005. Epub 2012 Nov 30.
10. Bohn T, Cocco E, Gourdol L, Guignard C, Hoffmann L: Determination of atrazine and degradation products in Luxembourgish drinking water: origin and fate of potential endocrine-disrupting pesticides. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2011 Aug;28(8):1041-54. doi: 10.1080/19440049.2011.580012. Epub 2011 Jun 27.
11. Davis AM, Lewis SE, Bainbridge ZT, Glendenning L, Turner RD, Brodie JE: Dynamics of herbicide transport and partitioning under event flow conditions in the lower Burdekin region, Australia. Mar Pollut Bull. 2012;65(4-9):182-93. doi: 10.1016/j.marpolbul.2011.08.025. Epub 2011 Sep 19.
12. Gunderson MP, Veldhoen N, Skirrow RC, Macnab MK, Ding W, van Aggelen G, Helbing CC: Effect of low dose exposure to the herbicide atrazine and its metabolite on cytochrome P450 aromatase and steroidogenic factor-1 mRNA levels in the brain of premetamorphic bullfrog tadpoles (Rana catesbeiana). Aquat Toxicol. 2011 Mar;102(1-2):31-8. doi: 10.1016/j.aquatox.2010.12.019. Epub 2011 Jan 4.
13. Ralston-Hooper KJ, Adamec J, Jannash A, Mollenhauer R, Ochoa-Acuna H, Sepulveda MS: Use of GC x GC/TOF-MS and LC/TOF-MS for metabolomic analysis of Hyalella azteca chronically exposed to atrazine and its primary metabolite, desethylatrazine. J Appl Toxicol. 2011 Jul;31(5):399-410. doi: 10.1002/jat.1587. Epub 2010 Sep 18.
14. Boisvert M, Fayad PB, Sauve S: Development of a new multi-residue laser diode thermal desorption atmospheric pressure chemical ionization tandem mass spectrometry method for the detection and quantification of pesticides and pharmaceuticals in wastewater samples. Anal Chim Acta. 2012 Nov 19;754:75-82. doi: 10.1016/j.aca.2012.09.046. Epub 2012 Oct 17.
15. Segura PA, MacLeod SL, Lemoine P, Sauve S, Gagnon C: Quantification of carbamazepine and atrazine and screening of suspect organic contaminants in surface and drinking waters. Chemosphere. 2011 Aug;84(8):1085-94. doi: 10.1016/j.chemosphere.2011.04.056. Epub 2011 May 12.
16. Ngigi AN, Getenga ZM, Dorfler U, Boga HI, Kuria B, Ndalut P, Schroll R: Effects of carbon amendment on in situ atrazine degradation and total microbial biomass. J Environ Sci Health B. 2013;48(1):40-8. doi: 10.1080/03601234.2012.716727.
17. Nguyen JV, Olsson AO, Bravo R, Needham LL, Barr DB: Quantification of atrazine, phenylurea, and sulfonylurea herbicide metabolites in urine by high-performance liquid chromatography-tandem mass spectrometry. J Anal Toxicol. 2007 May;31(4):181-6.
18. Vryzas Z, Papadakis EN, Vassiliou G, Papadopoulou-Mourkidou E: Occurrence of pesticides in transboundary aquifers of North-eastern Greece. Sci Total Environ. 2012 Dec 15;441:41-8. doi: 10.1016/j.scitotenv.2012.09.074. Epub 2012 Nov 6.
19. Schreglmann K, Hoeche M, Steinbeiss S, Reinnicke S, Elsner M: Carbon and nitrogen isotope analysis of atrazine and desethylatrazine at sub-microgram per liter concentrations in groundwater. Anal Bioanal Chem. 2013 Mar;405(9):2857-67. doi: 10.1007/s00216-012-6616-0. Epub 2012 Dec 30.
20. Ralston-Hooper KJ, Sanchez BC, Adamec J, Sepulveda MS: Proteomics in aquatic amphipods: can it be used to determine mechanisms of toxicity and interspecies responses after exposure to atrazine? Environ Toxicol Chem. 2011 May;30(5):1197-203. doi: 10.1002/etc.475. Epub 2011 Mar 9.
21. Ralston-Hooper K, Hardy J, Hahn L, Ochoa-Acuna H, Lee LS, Mollenhauer R, Sepulveda MS: Acute and chronic toxicity of atrazine and its metabolites deethylatrazine and deisopropylatrazine on aquatic organisms. Ecotoxicology. 2009 Oct;18(7):899-905. doi: 10.1007/s10646-009-0351-0. Epub 2009 Jun 16.
22. Ross MK, Filipov NM: Determination of atrazine and its metabolites in mouse urine and plasma by LC-MS analysis. Anal Biochem. 2006 Apr 15;351(2):161-73. Epub 2006 Feb 20.
23. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.