Showing Compound Card for Dicrotophos (CDB006221)

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Record Information
Version1.0
Created at2020-07-28 20:16:38 UTC
Updated at2020-11-18 16:40:15 UTC
CannabisDB IDCDB006221
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameDicrotophos
DescriptionDicrotophos, also known as bidrin or carbicron, belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain. Dicrotophos is an extremely weak basic (essentially neutral) compound (based on its pKa). Dicrotophos is a potentially toxic compound. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. For skin contact, the skin should be washed with soap and water.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(e)-2-Dimethylcarbamoyl-1-methylvinyl dimethyl phosphateChEBI
(e)-Phosphoric acid, 3-(dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl esterChEBI
3-(Dimethoxyphosphinyloxy)-N,N-dimethyl-cis-crotonamideChEBI
3-Dimethoxyphosphinoyloxy-N,N-dimethylisocrotonamideChEBI
BidrinChEBI
Dimethyl (e)-2-dimethyl-carbamoyl-1-methylvinyl phosphateChEBI
(e)-2-Dimethylcarbamoyl-1-methylvinyl dimethyl phosphoric acidGenerator
(e)-Phosphate, 3-(dimethylamino)-1-methyl-3-oxo-1-propenyl dimethyl esterGenerator
Dimethyl (e)-2-dimethyl-carbamoyl-1-methylvinyl phosphoric acidGenerator
Dicrotophos, (Z)-isomerMeSH
CarbicronMeSH
Dicrotophos, (e)-isomerMeSH
Chemical FormulaC8H16NO5P
Average Molecular Weight237.1901
Monoisotopic Molecular Weight237.076609139
IUPAC Name(2E)-3-[(dimethoxyphosphoryl)oxy]-N,N-dimethylbut-2-enamide
Traditional Namedicrotophos
CAS Registry Number141-66-2
SMILES
COP(=O)(OC)O\C(C)=C\C(=O)N(C)C
InChI Identifier
InChI=1S/C8H16NO5P/c1-7(6-8(10)9(2)3)14-15(11,12-4)13-5/h6H,1-5H3/b7-6+
InChI KeyVEENJGZXVHKXNB-VOTSOKGWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly two alkyl chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentDialkyl phosphates
Alternative Parents
Substituents
  • Dialkyl phosphate
  • N-acyl-amine
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.06ALOGPS
logP-0.24ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-0.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area65.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity56.54 m³·mol⁻¹ChemAxon
Polarizability21.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004i-8900000000-52216ebab57c05cd46252014-10-20View Spectrum
Predicted GC-MSDicrotophos, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03g0-0940000000-ee932f5702dfe3e9e8642016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2910000000-ad68546d385dbc4cea102016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xr-9700000000-ab7c9002d974acca88982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0290000000-6d5d76d8b754e0bb0d792016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002o-2960000000-6d18d7e24645eee58d0d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-325c5ea2a61b85905ea62016-08-03View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18656
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDicrotophos
METLIN IDNot Available
PubChem Compound5371560
PDB IDNot Available
ChEBI ID38658
References
General References
  1. Taylor A, Birkett JW: Pesticides in cannabis: A review of analytical and toxicological considerations. Drug Test Anal. 2020 Feb;12(2):180-190. doi: 10.1002/dta.2747. Epub 2020 Jan 19. [PubMed:31834671 ]
  2. Cuypers E, Vanhove W, Gotink J, Bonneure A, Van Damme P, Tytgat J: The use of pesticides in Belgian illicit indoor cannabis plantations. Forensic Sci Int. 2017 Aug;277:59-65. doi: 10.1016/j.forsciint.2017.05.016. Epub 2017 May 25. [PubMed:28609661 ]