Basic Info

Common NameBromomethane(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 IDF04347
CAS Number74-83-9
PubChem CID6323
FormulaCH3Br
IUPAC Name

bromomethane

InChI Key

GZUXJHMPEANEGY-UHFFFAOYSA-N

InChI

InChI=1S/CH3Br/c1-2/h1H3

Canonical SMILES

CBr

Isomeric SMILES

CBr

WikipediaBromomethane
Synonyms
        
            Bromomethane
        
            Monobromomethane
        
            METHYL BROMIDE
        
            74-83-9
        
            Methane, bromo-
        
            Embafume
        
            Terabol
        
            CH3Br
        
            Methylbromid
        
            Pestmaster
        
Classifies
                

                  
                    Pollutant
                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganohalogen compounds
ClassAlkyl halides
SubclassHalomethanes
Intermediate Tree NodesNot available
Direct ParentHalomethanes
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsHalomethane - Hydrocarbon derivative - Organobromide - Alkyl bromide - Aliphatic acyclic compound
DescriptionThis 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 NameProperty Value
Molecular Weight94.939
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count0
Rotatable Bond Count0
Complexity2
Monoisotopic Mass93.942
Exact Mass93.942
XLogP1
Formal Charge0
Heavy Atom Count2
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9726
Human Intestinal AbsorptionHIA+0.9927
Caco-2 PermeabilityCaco2+0.6966
P-glycoprotein SubstrateNon-substrate0.8605
P-glycoprotein InhibitorNon-inhibitor0.9777
Non-inhibitor0.9700
Renal Organic Cation TransporterNon-inhibitor0.8992
Distribution
Subcellular localizationLysosome0.6305
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7980
CYP450 2D6 SubstrateNon-substrate0.7322
CYP450 3A4 SubstrateNon-substrate0.7498
CYP450 1A2 InhibitorNon-inhibitor0.8186
CYP450 2C9 InhibitorNon-inhibitor0.9034
CYP450 2D6 InhibitorNon-inhibitor0.9587
CYP450 2C19 InhibitorNon-inhibitor0.9137
CYP450 3A4 InhibitorNon-inhibitor0.9766
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9273
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9643
Non-inhibitor0.9675
AMES ToxicityAMES toxic0.9074
CarcinogensCarcinogens 0.6849
Fish ToxicityLow FHMT0.6474
Tetrahymena Pyriformis ToxicityHigh TPT0.9430
Honey Bee ToxicityHigh HBT0.8233
BiodegradationNot ready biodegradable0.7807
Acute Oral ToxicityII0.7789
Carcinogenicity (Three-class)Non-required0.5192

Model Value Unit
Absorption
Aqueous solubility-0.7274LogS
Caco-2 Permeability1.5546LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.6160LD50, mol/kg
Fish Toxicity1.8846pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1825pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other HerbsBritain0.05mg/kg
Other Spinach & SimilarBritain0.05mg/kg
DatesBritain0.05mg/kg
Sweet PotatoesKorea30ppm
CherriesKorea20ppm
PomelosKorea30ppm
MaizeKorea50ppm
Ware PotatoesBritain0.05mg/kg
TeaBritain0.05mg/kg
HopBritain0.05mg/kg
Early PotatoesBritain0.05mg/kg
Other OilseedsBritain0.1mg/kg
Hemp SeedBritain0.1mg/kg
Cotton SeedBritain0.1mg/kg
Mustard SeedBritain0.1mg/kg
Soya BeanBritain0.1mg/kg
Rape SeedBritain0.1mg/kg
Sunflower SeedBritain0.1mg/kg
Sesame SeedBritain0.1mg/kg
Poppy SeedBritain0.1mg/kg

References

TitleJournalDatePubmed ID
Replacing methyl bromide with a combination of 1,3-dichloropropene and metamsodium for cucumber production in China.PLoS One2017 Nov 1629145472
Comprehensive estimate of the theoretical maximum daily intake of pesticideresidues for chronic dietary risk assessment in Argentina.J Environ Sci Health B2017 Apr 328085552
2, 3-Dimethylmaleic anhydride (3, 4-Dimethyl-2, 5-furandione): A plant derived insecticidal molecule from Colocasia esculenta var. esculenta (L.) Schott.Sci Rep2016 Feb 326837840
Phosphine fumigation and residues in dry-cured ham in commercial applications.Meat Sci2015 Sep25951409
Efficacy of Methyl Bromide for Control of Different Life Stages of Stored-ProductPsocids.J Econ Entomol2015 Jun26470271
Ethyl Formate Fumigation of Dry and Semidry Date Fruits: Experimental Kinetics,Modeling, and Lethal Effect on Carob Moth.J Econ Entomol2015 Jun26470221
Ethyl Formate: A Potential Disinfestation Treatment for Eucalyptus Weevil(Gonipterus platensis) (Coleoptera: Curculionidae) in Apples.J Econ Entomol2015 Dec26470387
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 Chem2015 Apr 125758836
Bioactivity of essential oil from Artemisia stolonifera (Maxim.) Komar. and itsmain compounds against two stored-product insects.J Oleo Sci201525757434
Evaluation of the combination of dimethyl disulfide and dazomet as an efficientmethyl bromide alternative for cucumber production in China.J Agric Food Chem2014 May 2824820184
Postharvest treatment of fresh fruit from California with methyl bromide forcontrol of light brown apple moth (Lepidoptera: Tortricidae).J Econ Entomol2013 Jun23865179
Postharvest control of western flower thrips (Thysanoptera: Thripidae) andCalifornia red scale (Hemiptera: Diaspididae) with ethyl formate and its impacton citrus fruit quality.J Econ Entomol2013 Dec24498732
Evaluation of chloropicrin gelatin capsule formulation as a soil fumigant forgreenhouse strawberry in China.J Agric Food Chem2012 May 2322551154
Ethyl formate plus methyl isothiocyanate--a potential liquid fumigant for stored grains.Pest Manag Sci2012 Feb21780282
Environmental impacts from pesticide use: a case study of soil fumigation inFlorida tomato production.Int J Environ Res Public Health2011 Dec22408594
Effects of phosphine and methyl bromide fumigation on the volatile flavor profileand sensory quality of dry cured ham.Meat Sci2010 Oct20554396
Fumigation characteristics of ozone in postharvest treatment of Kabkab dates(Phoenix dactylifera L.) against selected insect infestation.J Food Prot2010 Apr20377969
Studies on the toxicity of acetone, acrolein and carbon dioxide on stored-product insects and wheat seed.Pak J Biol Sci2008 Apr 118810963
Survival of Escherichia coli O157:H7 in soil and on lettuce after soil fumigation.Can J Microbiol2007 May17668021
Linkage of the California Pesticide Use Reporting Database with spatial land use data for exposure assessment.Environ Health Perspect2007 May17520053

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
  1. 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
  1. 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
  1. Yang RS, Witt KL, Alden CJ, Cockerham LG: Toxicology of methyl bromide. Rev Environ Contam Toxicol. 1995;142:65-85. [7652197 ]