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Record Information
Version2.0
Creation Date2009-06-17 23:53:03 UTC
Update Date2014-12-24 20:23:00 UTC
Accession NumberT3D0973
Identification
Common NameFosamine
ClassSmall Molecule
DescriptionFosamine is an organophosphate herbicide. Used as a foliar spray for control and/or growth suppression of many woody plant species such as maple, birch, alder, blackberry, vine maple, ash, and oak. Susceptible treated plants normally fail to refoliate during the growing season following treatment and subsequently die. Fosamine functions as a plant growth regulator. It is sometimes referred to as a “dormancy enforcer,” but its specific mechanism of action has not been identified. There is some evidence that it inhibits mitosis in susceptible plants.
Compound Type
  • Amine
  • Carbamate
  • Ester
  • Herbicide
  • Organic Compound
  • Organophosphate
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
Ethyl carbamoylphosphonic acid
Ethyl hydrogen carbamoylphosphonate
Monoethyl (aminocarbonyl)phosphonate
Phosphonic acid, (aminocarbonyl)-, monoethyl ester
Chemical FormulaC3H8NO4P
Average Molecular Mass153.074 g/mol
Monoisotopic Mass153.019 g/mol
CAS Registry Number59682-52-9
IUPAC Namecarbamoyl(ethoxy)phosphinic acid
Traditional Namefosamine
SMILESCCOP(O)(=O)C(N)=O
InChI IdentifierInChI=1S/C3H8NO4P/c1-2-8-9(6,7)3(4)5/h2H2,1H3,(H2,4,5)(H,6,7)
InChI KeyInChIKey=UCHDFLNGIZUADY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassOrganic phosphonic acids
Direct ParentOrganic phosphonic acids
Alternative Parents
Substituents
  • Organophosphonic acid
  • Carboximidic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility31.8 g/LALOGPS
logP-1ALOGPS
logP-0.73ChemAxon
logS-0.68ALOGPS
pKa (Strongest Acidic)1.25ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.62 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.13 m³·mol⁻¹ChemAxon
Polarizability12.18 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-9ddad6d9abffcf7ee27dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9600000000-eb27e2b147af968a995dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-9200000000-d69f49f92185a2e28ce5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2900000000-8420f295de5d8bb0a242JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adl-9800000000-c2a988dc2c60620ae19bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-38c9a5c534207ffca3fbJSpectraViewer
Toxicity Profile
Route of ExposureInhalation (1) ; oral (1); dermal (1)
Mechanism of ToxicityFosamine is an eye irritant. It likely binds to or modifies the TRPA1 protein which leads to a lachrymatory (tearing) response.
MetabolismMetabolism of organophosphates occurs principally by oxidation, and hydrolysis by esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Fosamine rapidly passes through the body; elimination is primarily in the feces and less in the urine. It does not bioaccumulate (build up) in mammals.
Toxicity ValuesThe oral LD50 is 24,400 mg/kg for rats
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed as a herbicide to control growth of woody plants.
Minimum Risk LevelNot Available
Health EffectsOccupational exposure to fosamine occurs through dermal contact and inhalation of dust and sprays, especially to workers applying the compound as a herbicide. Fosamine has low to very low toxicity if individuals accidentally inhale or eat residues and has moderate toxicity if touched. It is not irritating to the eyes, but it can cause mild to moderate skin irritation. Fosamine can cause moderate eye injury or irritation. In one subchronic oral study, the laboratory animals given the highest dose exhibited some statistically significant effects, including effects to the kidneys, bladder and decreases in body weight.
SymptomsFosamine has low to very low toxicity if individuals accidentally inhale or eat residues and has moderate toxicity if touched. It is not irritating to the eyes, but it can cause mild to moderate skin irritation. Fosamine is not a skin sensitizer.
TreatmentFor acute exposures and first aid: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID33257
ChEMBL IDNot Available
ChemSpider ID30725
KEGG IDC18789
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC019397
Stitch IDFosamine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D0973.pdf
General References
  1. IPCS Intox Database (1987). Antimony pentoxide. [Link]
  2. Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da