Bromomethane
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Basic Info
Common Name | Bromomethane(F04347) |
2D Structure | |
Description | Bromomethane (or methyl bromide) is an organobromide compound that may be produced both synthetically and by naturally marine organisms and certain terrestrial plants. It was used extensively as a pesticide and as a fire extinguisher component until being phased out by most countries in the early 2000s, as it is considered an ozone-depleting substance. The primary use of methyl bromide is/was as a fumigant in soil to control fungi, nematodes, and weeds; in space fumigation of food commodities (e.g., grains); and in storage facilities (such as mills, warehouses, vaults, ships, and freight cars) to control insects and rodents. Its popularity as a fumigant is largely attributable to its high toxicity to many pests, the variety of settings in which it can be applied, its ability to penetrate the fumigated substances, and its rapid dissipation following application. Trace amounts of methyl bromide have been detected in drinking water. There are many reports of humans who have died following acute inhalation exposure to bromomethane. Most cases have involved accidental exposures associated with manufacturing or packaging operations, use of fire extinguishers containing bromomethane, or fumigation activities. Death is not immediate, but usually occurs within l-2 days of exposure. The cause of death is not certain, but is probably due to neurological and lung injury. |
FRCD ID | F04347 |
CAS Number | 74-83-9 |
PubChem CID | 6323 |
Formula | CH3Br |
IUPAC Name | bromomethane |
InChI Key | GZUXJHMPEANEGY-UHFFFAOYSA-N |
InChI | InChI=1S/CH3Br/c1-2/h1H3 |
Canonical SMILES | CBr |
Isomeric SMILES | CBr |
Wikipedia | Bromomethane |
Synonyms | Bromomethane Monobromomethane METHYL BROMIDE 74-83-9 Methane, bromo- Embafume Terabol CH3Br Methylbromid Pestmaster |
Classifies | Pollutant Pesticide |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organohalogen compounds |
Class | Alkyl halides |
Subclass | Halomethanes |
Intermediate Tree Nodes | Not available |
Direct Parent | Halomethanes |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | Halomethane - Hydrocarbon derivative - Organobromide - Alkyl bromide - Aliphatic acyclic compound |
Description | This compound belongs to the class of organic compounds known as halomethanes. These are organic compounds in which at least one of the four hydrogen atoms of methane (CH4) are replaced by halogen atoms. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 94.939 |
Hydrogen Bond Donor Count | 0 |
Hydrogen Bond Acceptor Count | 0 |
Rotatable Bond Count | 0 |
Complexity | 2 |
Monoisotopic Mass | 93.942 |
Exact Mass | 93.942 |
XLogP | 1 |
Formal Charge | 0 |
Heavy Atom Count | 2 |
Defined Atom Stereocenter Count | 0 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.9726 |
Human Intestinal Absorption | HIA+ | 0.9927 |
Caco-2 Permeability | Caco2+ | 0.6966 |
P-glycoprotein Substrate | Non-substrate | 0.8605 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9777 |
Non-inhibitor | 0.9700 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8992 |
Distribution | ||
Subcellular localization | Lysosome | 0.6305 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7980 |
CYP450 2D6 Substrate | Non-substrate | 0.7322 |
CYP450 3A4 Substrate | Non-substrate | 0.7498 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8186 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9034 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9587 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9137 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9766 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9273 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9643 |
Non-inhibitor | 0.9675 | |
AMES Toxicity | AMES toxic | 0.9074 |
Carcinogens | Carcinogens | 0.6849 |
Fish Toxicity | Low FHMT | 0.6474 |
Tetrahymena Pyriformis Toxicity | High TPT | 0.9430 |
Honey Bee Toxicity | High HBT | 0.8233 |
Biodegradation | Not ready biodegradable | 0.7807 |
Acute Oral Toxicity | II | 0.7789 |
Carcinogenicity (Three-class) | Non-required | 0.5192 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.7274 | LogS |
Caco-2 Permeability | 1.5546 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 2.6160 | LD50, mol/kg |
Fish Toxicity | 1.8846 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | 0.1825 | pIGC50, ug/L |
MRLs
Food | Product Code | Country | MRLs | Application Date | Notes |
---|---|---|---|---|---|
Other Herbs | Britain | 0.05mg/kg | |||
Other Spinach & Similar | Britain | 0.05mg/kg | |||
Dates | Britain | 0.05mg/kg | |||
Sweet Potatoes | Korea | 30ppm | |||
Cherries | Korea | 20ppm | |||
Pomelos | Korea | 30ppm | |||
Maize | Korea | 50ppm | |||
Ware Potatoes | Britain | 0.05mg/kg | |||
Tea | Britain | 0.05mg/kg | |||
Hop | Britain | 0.05mg/kg | |||
Early Potatoes | Britain | 0.05mg/kg | |||
Other Oilseeds | Britain | 0.1mg/kg | |||
Hemp Seed | Britain | 0.1mg/kg | |||
Cotton Seed | Britain | 0.1mg/kg | |||
Mustard Seed | Britain | 0.1mg/kg | |||
Soya Bean | Britain | 0.1mg/kg | |||
Rape Seed | Britain | 0.1mg/kg | |||
Sunflower Seed | Britain | 0.1mg/kg | |||
Sesame Seed | Britain | 0.1mg/kg | |||
Poppy Seed | Britain | 0.1mg/kg |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Replacing methyl bromide with a combination of 1,3-dichloropropene and metamsodium for cucumber production in China. | PLoS One | 2017 Nov 16 | 29145472 |
Comprehensive estimate of the theoretical maximum daily intake of pesticideresidues for chronic dietary risk assessment in Argentina. | J Environ Sci Health B | 2017 Apr 3 | 28085552 |
2, 3-Dimethylmaleic anhydride (3, 4-Dimethyl-2, 5-furandione): A plant derived insecticidal molecule from Colocasia esculenta var. esculenta (L.) Schott. | Sci Rep | 2016 Feb 3 | 26837840 |
Phosphine fumigation and residues in dry-cured ham in commercial applications. | Meat Sci | 2015 Sep | 25951409 |
Efficacy of Methyl Bromide for Control of Different Life Stages of Stored-ProductPsocids. | J Econ Entomol | 2015 Jun | 26470271 |
Ethyl Formate Fumigation of Dry and Semidry Date Fruits: Experimental Kinetics,Modeling, and Lethal Effect on Carob Moth. | J Econ Entomol | 2015 Jun | 26470221 |
Ethyl Formate: A Potential Disinfestation Treatment for Eucalyptus Weevil(Gonipterus platensis) (Coleoptera: Curculionidae) in Apples. | J Econ Entomol | 2015 Dec | 26470387 |
Activated carbons from end-products of tree nut and tree fruit production assorbents for removing methyl bromide in ventilation effluent followingpostharvest chamber fumigation. | J Agric Food Chem | 2015 Apr 1 | 25758836 |
Bioactivity of essential oil from Artemisia stolonifera (Maxim.) Komar. and itsmain compounds against two stored-product insects. | J Oleo Sci | 2015 | 25757434 |
Evaluation of the combination of dimethyl disulfide and dazomet as an efficientmethyl bromide alternative for cucumber production in China. | J Agric Food Chem | 2014 May 28 | 24820184 |
Postharvest treatment of fresh fruit from California with methyl bromide forcontrol of light brown apple moth (Lepidoptera: Tortricidae). | J Econ Entomol | 2013 Jun | 23865179 |
Postharvest control of western flower thrips (Thysanoptera: Thripidae) andCalifornia red scale (Hemiptera: Diaspididae) with ethyl formate and its impacton citrus fruit quality. | J Econ Entomol | 2013 Dec | 24498732 |
Evaluation of chloropicrin gelatin capsule formulation as a soil fumigant forgreenhouse strawberry in China. | J Agric Food Chem | 2012 May 23 | 22551154 |
Ethyl formate plus methyl isothiocyanate--a potential liquid fumigant for stored grains. | Pest Manag Sci | 2012 Feb | 21780282 |
Environmental impacts from pesticide use: a case study of soil fumigation inFlorida tomato production. | Int J Environ Res Public Health | 2011 Dec | 22408594 |
Effects of phosphine and methyl bromide fumigation on the volatile flavor profileand sensory quality of dry cured ham. | Meat Sci | 2010 Oct | 20554396 |
Fumigation characteristics of ozone in postharvest treatment of Kabkab dates(Phoenix dactylifera L.) against selected insect infestation. | J Food Prot | 2010 Apr | 20377969 |
Studies on the toxicity of acetone, acrolein and carbon dioxide on stored-product insects and wheat seed. | Pak J Biol Sci | 2008 Apr 1 | 18810963 |
Survival of Escherichia coli O157:H7 in soil and on lettuce after soil fumigation. | Can J Microbiol | 2007 May | 17668021 |
Linkage of the California Pesticide Use Reporting Database with spatial land use data for exposure assessment. | Environ Health Perspect | 2007 May | 17520053 |
Targets
- General Function:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.
- Gene Name:
- HBA1
- Uniprot ID:
- P69905
- Molecular Weight:
- 15257.405 Da
References
- Yang RS, Witt KL, Alden CJ, Cockerham LG: Toxicology of methyl bromide. Rev Environ Contam Toxicol. 1995;142:65-85. [7652197 ]
- General Function:
- Oxygen transporter activity
- Specific Function:
- Involved in oxygen transport from the lung to the various peripheral tissues.LVV-hemorphin-7 potentiates the activity of bradykinin, causing a decrease in blood pressure.Spinorphin: functions as an endogenous inhibitor of enkephalin-degrading enzymes such as DPP3, and as a selective antagonist of the P2RX3 receptor which is involved in pain signaling, these properties implicate it as a regulator of pain and inflammation.
- Gene Name:
- HBB
- Uniprot ID:
- P68871
- Molecular Weight:
- 15998.34 Da
References
- Yang RS, Witt KL, Alden CJ, Cockerham LG: Toxicology of methyl bromide. Rev Environ Contam Toxicol. 1995;142:65-85. [7652197 ]
- 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
References
- Yang RS, Witt KL, Alden CJ, Cockerham LG: Toxicology of methyl bromide. Rev Environ Contam Toxicol. 1995;142:65-85. [7652197 ]