| Record Information |
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| Version | 2.0 |
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| Creation Date | 2009-06-17 23:53:05 UTC |
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| Update Date | 2014-12-24 20:23:01 UTC |
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| Accession Number | T3D0994 |
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| Identification |
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| Common Name | Phenmedipham |
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| Class | Small Molecule |
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| Description | Phenmedipham is a selective herbicide of the carbanilate and biscarbamate classes. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. Phenmedipham was developed by Schering AG and approved for use in the United States in 1970. Today, about 100 tons of Phenmedipham are used each year. It is commonly used in beet, spinach, and strawberry crops to protect against weeds, often in comination with Desmedipham under the trade names Betanal or Betamax. (3) |
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| Compound Type | - Amine
- Carbamate
- Ester
- Ether
- Herbicide
- Organic Compound
- Pesticide
- Synthetic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | 3-((Methoxycarbonyl)amino)phenyl (3-methylphenyl)carbamate | | 3-(Carbomethoxyamino)phenyl 3-methylcarbanilate | | 3-Methoxycarbonyl-N-(3'-methylphenyl)-carbamat | | 3-Methoxycarbonylaminophenyl 3'-methylcarbanilate | | 3-Methoxycarbonylaminophenyl N-3'-methylphenylcarbamate | | 3-[(Methoxycarbonyl)amino]phenyl (3-methylphenyl)carbamate | | Alegro | | Beetomax | | Beetup | | BETA | | Betaflow | | Betalion | | Betamix | | Betanal | | Betanal e | | Betanal tandem | | Betosip | | Caswell No. 648B | | Ethofumesate-phenmedipham | | Fender | | Fenmedifam | | Goliath | | Gusto | | Headland dephend | | Kemifam | | m-Hydroxycarbanilic acid methyl ester m-methylcarbanilate | | Medipham | | Methyl 3-(3-methylcarbaniloyloxy)carbanilate | | Methyl 3-(m-tolylcarbamoyloxy)phenylcarbamate | | Methyl m-hydroxycarbanilate m-methylcarbanilate | | Methyl m-hydroxycarbanilate m-methylcarbanilate (ester) | | Methyl m-hydroxycarbanilate, m-methylcarbanilate | | Methyl-3-(3-methylcarbaniloyloxy) carbanilate | | Methyl-3-hydroxycarbanilate-3-methylcarbanilate | | Methyl-3-m-tolycarbamoloxyphenyl carbamate | | Morton EP 452 | | Phendipham | | Phenmediphame | | Pistol | | Pistol 400 | | Protrum k | | Schering 4072 | | Spin-aid | | Suplex | | Synbetan p | | Tripart beta | | Tripart beta 2 | | Vangard | | Vanguard |
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| Chemical Formula | C16H16N2O4 |
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| Average Molecular Mass | 300.309 g/mol |
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| Monoisotopic Mass | 300.111 g/mol |
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| CAS Registry Number | 13684-63-4 |
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| IUPAC Name | 1-3-{[hydroxy(methoxy)methylidene]amino}phenoxy-N-(3-methylphenyl)methanimidic acid |
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| Traditional Name | 1-3-{[hydroxy(methoxy)methylidene]amino}phenoxy-N-(3-methylphenyl)methanimidic acid |
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| SMILES | COC(O)=NC1=CC(OC(O)=NC2=CC=CC(C)=C2)=CC=C1 |
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| InChI Identifier | InChI=1S/C16H16N2O4/c1-11-5-3-6-12(9-11)18-16(20)22-14-8-4-7-13(10-14)17-15(19)21-2/h3-10H,1-2H3,(H,17,19)(H,18,20) |
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| InChI Key | InChIKey=IDOWTHOLJBTAFI-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as phenylcarbamic acid esters. These are ester derivatives of phenylcarbamic acids. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Phenylcarbamic acid esters |
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| Direct Parent | Phenylcarbamic acid esters |
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| Alternative Parents | |
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| Substituents | - Phenylcarbamic acid ester
- Phenoxy compound
- Toluene
- Carbamic acid ester
- Carbonic acid derivative
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Carbonyl group
- 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 | | Name | SMPDB Link | KEGG Link |
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| Metabolic Pathways | Not Available | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | Colorless and odorless powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 143-144 °C | | Boiling Point | Decomposition at> 200 °C | | Solubility | Practically insoluble in water (4.7 mg/L); soluble in polar organic solvents | | 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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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-0910000000-f30d7fef5d59b6c5ce93 | 2021-09-24 | 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 (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-000i-0900000000-00031c14ca44e9139da9 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-014r-0900000000-58c2bf322552cc023a2c | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-000i-0900000000-48fd93926a23be06e22f | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-000i-0900000000-e0ddaebfe93fd113eec8 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0900000000-ec1e788887825ffd4f0c | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0900000000-f503ecc696af8c003a6e | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-000i-0900000000-73e4c8828d11574f5451 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-014i-0900000000-285f09d3c2697ef6975a | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 75V, Positive | splash10-052r-3900000000-1c4f4f8b000368ac97de | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-06el-8900000000-89453a33a33ec2ad9279 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 60V, Positive | splash10-000i-1900000000-6a34a96bdb4b2086cd06 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-000i-0900000000-0fbfef39b582949ab789 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-014i-0900000000-aba50b6e242108613201 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-000i-0900000000-6c56388e0bc4b72f9781 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-000i-0900000000-9f94251a5005a58d3751 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 60V, Positive | splash10-000i-1900000000-308e1ba29a7937090320 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-014r-0900000000-1a043edb4709fa7aad1d | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 75V, Positive | splash10-052r-3900000000-dcc4c2258728e16c13a9 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-06el-8900000000-1ec41aa995a5fb8c1e67 | 2021-09-20 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00lr-0960000000-7f9c2c8524e4108413e5 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00lr-0930000000-35b7fc9406bb7cece661 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-0900000000-b8bb1126db209fc546e1 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0gb9-0915000000-63d6e03ed88c54642817 | 2016-08-02 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014i-0910000000-29a9b44697d8a365aa4a | 2016-08-02 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00m0-2900000000-9af527c638cac566c742 | 2016-08-02 | View Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-00lr-5900000000-18214c4b9332b3821a3e | 2014-09-20 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Inhalation (2) ; oral (2); dermal (2) |
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| Mechanism of Toxicity | Phenmedipham is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. 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. |
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| Metabolism | The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (2) |
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| Toxicity Values | LD50: >8000 mg/kg (Rat, oral) |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Phenmedipham is a selective herbicide commonly used in beet, spinach, and strawberry crops to protect against weeds, often in comination with Desmedipham. |
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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. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing. (1) |
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| Symptoms | As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (3) |
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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 | 24744 |
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| ChEMBL ID | CHEMBL1079421 |
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| ChemSpider ID | 23134 |
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| KEGG ID | C18420 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | Not Available |
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| BioCyc ID | CPD-6967 |
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| CTD ID | C100128 |
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| Stitch ID | Phenmedipham |
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| PDB ID | Not Available |
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| ACToR ID | 6509 |
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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 | Not Available |
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| General References | - Roldan-Tapia L, Nieto-Escamez FA, del Aguila EM, Laynez F, Parron T, Sanchez-Santed F: Neuropsychological sequelae from acute poisoning and long-term exposure to carbamate and organophosphate pesticides. Neurotoxicol Teratol. 2006 Nov-Dec;28(6):694-703. Epub 2006 Aug 30. [17029710 ]
- IPCS Intox Database (1987). Antimony pentoxide. [Link]
- Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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