| Record Information |
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| Version | 2.0 |
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| Creation Date | 2009-07-30 17:58:52 UTC |
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| Update Date | 2014-12-24 20:26:07 UTC |
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| Accession Number | T3D3503 |
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| Identification |
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| Common Name | Fenthion |
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| Class | Small Molecule |
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| Description | Fenthion is an organophosphate used primarily as an insecticide and secondarily as an avicide and acaricide. It was used extensively preharvest on sugar cane, rice, field corn, beets, pome and stone fruit, citrus fruits, pistachio, cotton, olives, coffee, cocoa, vegetables, and vines. However, fenthion no longer has Food and Drug Administration approval because of an excess number of poisoning related deaths (occur mostly by ingestion). Fenthion is neurotoxic. (3) (4) |
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| Compound Type | - Ester
- Ether
- Food Toxin
- Organic Compound
- Organophosphate
- Pesticide
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | 4-Methylmercapto-3-methylphenyl dimethyl thiophosphate | | Mercaptophos | | MPP | | O,O-Dimethyl O-4-(methylmercapto)-3-methylphenyl phosphorothioate | | O,O-Dimethyl O-4-methylthio-m-tolyl phosphorothioate | | O,O-Dimethyl O-[3-methyl-4-(methylsulfanyl)phenyl] thiophosphate | | O,O-Dimethyl-O-4-(methylmercapto)-3-methylphenyl thiophosphate | | Phosphorothioic acid, O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl) ester |
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| Chemical Formula | C10H15O3PS2 |
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| Average Molecular Mass | 278.328 g/mol |
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| Monoisotopic Mass | 278.020 g/mol |
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| CAS Registry Number | 55-38-9
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| IUPAC Name | O,O-dimethyl O-3-methyl-4-(methylsulfanyl)phenyl phosphorothioate |
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| Traditional Name | fenthion |
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| SMILES | COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 |
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| InChI Identifier | InChI=1S/C10H15O3PS2/c1-8-7-9(5-6-10(8)16-4)13-14(15,11-2)12-3/h5-7H,1-4H3 |
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| InChI Key | InChIKey=PNVJTZOFSHSLTO-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Organic thiophosphoric acids and derivatives |
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| Sub Class | Thiophosphoric acid esters |
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| Direct Parent | Phenyl thiophosphates |
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| Alternative Parents | |
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| Substituents | - Phenyl thiophosphate
- Phenoxy compound
- Aryl thioether
- Thiophosphate triester
- Thiophenol ether
- Toluene
- Alkylarylthioether
- Monocyclic benzene moiety
- Benzenoid
- Thioether
- Sulfenyl compound
- Organosulfur compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | |
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| Biological Roles | |
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| Chemical Roles | |
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| Physical Properties |
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| State | Liquid |
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| Appearance | Colourless oily liquid with characteristic odour. (2) |
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| Experimental Properties | | Property | Value |
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| Melting Point | 7.5°C | | Boiling Point | 87 °C (at 0.01 mmHg) | | Solubility | 54-56 ppm (at 20 °C) | | LogP | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00os-4930000000-d917f6fe7c279d0326ef | 2017-09-12 | View Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00os-4930000000-d917f6fe7c279d0326ef | 2018-05-18 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ik9-1970000000-38f4eb65b0f142b27c42 | 2017-09-01 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-004i-0090000000-cfc6cc7271f15039d91e | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-014j-0940000000-4c4cfaec8b9d90f02220 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0gb9-0910000000-30762456be8c99676446 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0gi0-0900000000-fc2e0d1f56a644607b35 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , positive | splash10-001i-0290000000-9da11dc2725fc111b8c4 | 2017-09-14 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-014j-0940000000-199b003861522f4b62e1 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0gb9-0910000000-14a50b7ed49de35229bc | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0gi0-0900000000-fc2e0d1f56a644607b35 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-0g4i-0900000000-daf8e3082dcd599a9ef6 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-0g4i-0900000000-677923a06bbdab3e4faa | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0v4i-0910000000-d74e5478dcae4fb77f71 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0g4i-0900000000-c7ed3dac5d73de1abfe2 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-001i-0290000000-c4282f269db3a3c433b7 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-014j-0940000000-49b2bd577f2239e1eeed | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0090000000-03e61a06874c5e65189c | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-0g4i-0900000000-89a0ce8c9a4d4a49d57c | 2021-09-20 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0190000000-74fefa9007324dd9847e | 2016-08-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002r-1970000000-6492e585fe189b3d02a0 | 2016-08-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01pc-9880000000-8949ee35385684bf0416 | 2016-08-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-005c-0290000000-b55d858a805aaba2db82 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-003r-0290000000-6e342595466184c4595b | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-2900000000-eb2a165616e3235fce1d | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-0190000000-953bec3de0724b9038a4 | 2021-09-23 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004u-4790000000-c6f5d3f2adc0c2093b0b | 2021-09-23 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-004i-7970000000-bc43a51c3e0e0f2a8537 | 2014-09-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental) | Not Available | 2014-09-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 100.40 MHz, CDCl3, experimental) | Not Available | 2014-09-23 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Oral (L1681 |
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| Mechanism of Toxicity | Fenthion is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen. |
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| Metabolism | 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. |
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| Toxicity Values | LD50: 330 mg/kg (Dermal, Rat) (3)
LD50: 190 to 615 mg/kg (Oral, Rat) (3) |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Spraying and application of nonarsenical insecticides entail exposures that are probably carcinogenic to humans (Group 2A). (6) |
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| Uses/Sources | The general population is not likely to be exposed to large amounts of fenthion. Occupational exposure to fenthion occurs through dermal contact and inhalation of dust and sprays, especially to workers applying the compound as an insecticide. Because fenthion has been detected in American foods, exposure to the general population can occur through consumption of foods containing fenthion residues. (3) |
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| Minimum Risk Level | Not Available |
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| Health Effects | Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides. |
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| Symptoms | The symptoms after inhalation and skin contact are: dizziness, nausea, vomiting, sweating, pupillary constriction, muscle cramp, excessive salivation, laboured breathing, convulsions, unconsciousness. The same symptoms occur after ingestion, with additionally abdominal cramps, diarrhoea, nausea and vomiting. In case of eye contact, blurred vision occurs. (2) |
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| Treatment | If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally. |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| PubChem Compound ID | 3346 |
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| ChEMBL ID | CHEMBL1604375 |
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| ChemSpider ID | 3229 |
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| KEGG ID | C14420 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 34761 |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Fenthion |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | T3D3503.pdf |
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| General References | - Marrs TC: Organophosphate poisoning. Pharmacol Ther. 1993;58(1):51-66. [8415873 ]
- International Programme on Chemical Safety (IPCS) INCHEM (2006). International Chemical Safety Cards (ICSCs). Fenthion. [Link]
- ATSDR - Agency for Toxic Substances and Disease Registry (2005). Toxicologic information about insecticides used for eradicating mosquitoes (West e Virus Control). Fenthion. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- Wikipedia. Fenthion. Last updated 13 July 2009. [Link]
- International Programme on Chemical Safety (IPCS) INCHEM (1976). Pesticide Document for Fenthion. [Link]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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| Down-Regulated Genes | Not Available |
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