 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C12H17NO2 |
| Molecular Weight | 207.27 |
| Exact Mass | 207.125 |
| CAS # | 3766-81-2 |
| Related CAS # | Fenobucarb-d3;2662756-72-9 |
| PubChem CID | 19588 |
| Appearance | Colorless to light yellow oil |
| Density | 1.0±0.1 g/cm3 |
| Boiling Point | 282.5±23.0 °C at 760 mmHg |
| Flash Point | 124.7±22.6 °C |
| Vapour Pressure | 0.0±0.6 mmHg at 25°C |
| Index of Refraction | 1.505 |
| LogP | 3.04 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 15 |
| Complexity | 206 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CCC(C1=CC=CC=C1OC(NC)=O)C |
| InChi Key | DIRFUJHNVNOBMY-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C12H17NO2/c1-4-9(2)10-7-5-6-8-11(10)15-12(14)13-3/h5-9H,4H2,1-3H3,(H,13,14) |
| Chemical Name | (2-butan-2-ylphenyl) N-methylcarbamate |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ADME/Pharmacokinetics |
Metabolism / Metabolites The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793) |
| Toxicity/Toxicokinetics |
Toxicity Summary Fenobucarb 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. |
| References |
[1]. Fenobucarb-induced developmental neurotoxicity and mechanisms in zebrafish. Neurotoxicology. 2020 Jul;79:11-19. [2]. Fenobucarb induces heart failure and cerebral hemorrhage in zebrafish. Aquat Toxicol. 2019 Apr;209:34-41. |
| Additional Infomation |
Fenobucarb is a carbamate ester obtained by the formal condensation of 2-sec-butylphenol with methylcarbamic acid. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an agrochemical, a herbicide, an insecticide and an environmental contaminant. It is functionally related to a methylcarbamic acid and a 2-sec-butylphenol. Fenobucarb is a synthetic carbamate ester compound and carbamate acetylcholinesterase inhibitor that is used as a pesticide. It is characterized as an oily yellow liquid, and exposure occurs by inhalation, ingestion, or contact. Fenobucarb is a carbamate pesticide. 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. (L795) |
Solubility Data
| Solubility (In Vitro) | DMSO : 100 mg/mL (482.46 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.06 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (12.06 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (12.06 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8246 mL | 24.1231 mL | 48.2462 mL | |
| 5 mM | 0.9649 mL | 4.8246 mL | 9.6492 mL | |
| 10 mM | 0.4825 mL | 2.4123 mL | 4.8246 mL |