Basic information
- Standard SMILES
CCOP(O)(=S)OCC- InChIKey
PKUWKAXTAVNIJR-UHFFFAOYSA-N- Molecular formula
- C4H11O3PS
- Average molar mass
- 170.17 g/mol
- Monoisotopic mass
- 170.01665184
Overview
O,O-diethyl hydrogen thiophosphate is an organic thiophosphate that is the diethyl ester of phosphorothioic O,O,O-acid. It has a role as a mouse metabolite and a human xenobiotic metabolite. It is a conjugate acid of an O,O-diethyl thiophosphate.
Names & identifiers
- Preferred name
- O,O-diethyl phosphorothioate
- IUPAC
- diethoxy-hydroxy-sulfanylidene-λ5-phosphane
- English name
- O,O-Diethyl thiophosphate, potassium salt
- Molecular formula
- C4H11O3PS
- Molecular weight
- 170.17
Names & synonyms
Show more names
Database identifiers
- CAS
2465-65-8、5871-17-0- PubChem CID
- 655
- DTXSID
DTXSID9052844- ChEMBL
CHEMBL1232328- ChEBI
CHEBI:28006- UNII
- FND2ADQ374
- Nikkaji
- J80.493B
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 70.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 106
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 180 · 180-186 °C(lit.)
- Boiling point
- 105 · 105-106 °C(Press: 2 Torr)
- Density
- 1.1806 g/cm3 · 1.1806 g/cm3
- pka
- -0.1 · -0.10±0.34(Predicted)
- FDA UNII
- 2 ADQ374 · FND2ADQ374
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 3 · 3
Safety & regulation
Toxicology
Toxicity Summary
Diethylthiophosphate (DETP) induces DNA damage only in the hepatic cell lines, and this effect could be related to a secondary non-diffusible metabolite generated by the activity of P450 enzymes since P450 enzyme inhibitors also inhibited the induction of DNA damage in hepatic cells. This organophosphorous (OP) metabolite has shown some toxicity in human peripheral blood mononucleated cells (PBMC). DETP is a cytotoxic compound in human PBMC. A relationship between urinary levels of DETP and the number of sperm susceptible to chromatin alteration has been reported among rural agricultural workers. In addition, a correlation between the frequency of aneuploidy in sperm and the levels of DETP in urine was identified in a rural population exposed to OP pesticides, indicating that the potential for genotoxicity following OP exposure may depend on the type and quantity of specific metabolites produced, such as DETP. (A15411)
Safety data
- wgk
- 3
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Diethyl thiophosphate is a known human metabolite of Diazinon.
Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via 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. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Uses & manufacturing
Upstream & downstream products
Downstream products
Suppliers8 total
Additional notes
DefinitionThe distance from the top to the bottom of an object, measured in units of length.
Related reactions
Linked notes
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