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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:43:50 UTC

Update Date

2022-03-07 02:53:01 UTC

HMDB ID

HMDB0031524

Secondary Accession Numbers

HMDB31524

Metabolite Identification

Common Name

Bromomethane

Description

Principally used as an insecticidal and nemacidal fumigant, especially for soil and agricultural produce. Also used as a solvent for extraction of plant oils The chemical compound bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and particularly biologically. It is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Brommethan	ChEBI
CH3BR	ChEBI
Embafume	ChEBI
MeBr	ChEBI
Methyl bromide	ChEBI
Methylbromid	ChEBI
Monobrommethan	ChEBI
Monobromomethane	ChEBI
Bercema	HMDB
BMM	HMDB
Brom-methan	HMDB
Brom-O-gas	HMDB
Brom-O-gas methyl bromide soil fumigant	HMDB
Brom-O-gaz	HMDB
Brom-O-sol	HMDB
Bromo-methane	HMDB
Bromometano	HMDB
Bromur di metile	HMDB
Bromure de methyle	HMDB
Bromuro di metile	HMDB
Broommethaan	HMDB
Celfume	HMDB
Chlorodibromomethane	HMDB
Curafume	HMDB
Dawson 100	HMDB
Detia gas ex-m	HMDB
Dow fume MC2	HMDB
Dowfume	HMDB
Dowfume MC-2	HMDB
Dowfume MC-2 fumigant	HMDB
Dowfume MC-2 soil fumigant	HMDB
Dowfume MC-2R	HMDB
Dowfume MC-33	HMDB
Drexel plant bed gas	HMDB
EDCO	HMDB
Fumigant-1	HMDB
Fumigant-1 (obs.)	HMDB
Halon 1001	HMDB
Haltox	HMDB
Iscobrome	HMDB
Kayafume	HMDB
m-b-c Fumigant	HMDB
MB	HMDB
MBC Soil fumigant	HMDB
MBC-33 Soil fumigant	HMDB
MBX	HMDB
Meb R	HMDB
Merth-O-gas	HMDB
Metafume	HMDB
Meth-O-gas	HMDB
Methogas	HMDB
Methyl bromide as a structural fumigant	HMDB
Methyl bromide rodent fumigant (with chloropicrin)	HMDB
Methyl bromide, 14C-labeled	HMDB
Methyl bromide, bsi, iso, jmaf	HMDB
Methyl fume	HMDB
Methylbromide	HMDB
Metylu bromek	HMDB
Pestmaster	HMDB
Pestmaster (obs.)	HMDB
Pestmaster soil fumigant-1	HMDB
Profume	HMDB
Profume (obs.)	HMDB
R 40b1	HMDB
Rfdfif@	HMDB
Rotox	HMDB
Superior methyl bromide-2	HMDB
Terabol	HMDB
Terr-O-cide II	HMDB
Terr-O-gas	HMDB
Terr-O-gas 100	HMDB
Terr-O-gas 67	HMDB
Tri-brom	HMDB
Zytox	HMDB

Chemical Formula

CH₃Br

Average Molecular Weight

94.939

Monoisotopic Molecular Weight

93.941812743

IUPAC Name

bromomethane

Traditional Name

methyl bromide

CAS Registry Number

74-83-9

SMILES

CBr

InChI Identifier

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

InChI Key

GZUXJHMPEANEGY-UHFFFAOYSA-N

Chemical Taxonomy

Description

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.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Alkyl halides

Sub Class

Halomethanes

Direct Parent

Halomethanes

Alternative Parents

Substituents

Halomethane
Hydrocarbon derivative
Organobromide
Alkyl bromide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

one-carbon compound (CHEBI:39275 )
methyl halides (CHEBI:39275 )
bromomethanes (CHEBI:39275 )
Pesticides (C18447 )
a bromide (CPD-12221 )

Ontology

Physiological effect

Health effect

Observation

Respiratory system disorder

Pulmonary disorder

Pulmonary edema (HMDB: HMDB0031524)

Renal system and urinary system

Renal disorder

Anuria (HMDB: HMDB0031524)
Proteinuria (HMDB: HMDB0031524)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Mood disorder

Apathy (HMDB: HMDB0031524)

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0031524)
Cytoplasm (HMDB: HMDB0031524)

Route of exposure

Parenteral

Dermal (HMDB: HMDB0031524)
Inhalation (HMDB: HMDB0031524)

Enteral

Ingestion (HMDB: HMDB0031524)

Source

Endogenous

Endogenous (HMDB: HMDB0031524)

Exogenous

Food

Food (HMDB: HMDB0031524)

Exogenous (HMDB: HMDB0031524)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Glutathione Metabolism (HMDB: HMDB0031524)
Glutathione Metabolism (PathBank: SMP0063622)

Disease pathway

5-Oxoprolinuria (PathBank: SMP0120446)
Gamma-Glutamyltranspeptidase Deficiency (PathBank: SMP0120566)
Gamma-Glutamyltransferase Deficiency (PathBank: SMP0120480)
Glutathione Synthetase Deficiency (PathBank: SMP0120485)
5-Oxoprolinase Deficiency (PathBank: SMP0120565)

Role

Environmental role

Air pollutant (HMDB: HMDB0031524)

Industrial application

Manufacturing industry

Laboratory chemical

Laboratory chemical (HMDB: HMDB0031524)

Agriculture

Pesticide

Fumigant insecticide (HMDB: HMDB0031524)

Biological role

Marine metabolite (HMDB: HMDB0031524)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-93.7 °C	Not Available
Boiling Point	3.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	15.2 mg/mL at 25 °C	Not Available
LogP	1.19	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	28.6 g/L	ALOGPS
logP	0.68	ALOGPS
logP	1.02	ChemAxon
logS	-0.52	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	14.3 m³·mol⁻¹	ChemAxon
Polarizability	5.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	113.355	30932474
DeepCCS	[M-H]-	111.54	30932474
DeepCCS	[M-2H]-	146.764	30932474
DeepCCS	[M+Na]+	120.392	30932474
AllCCS	[M+H]+	135.1	32859911
AllCCS	[M+H-H2O]+	130.8	32859911
AllCCS	[M+NH4]+	139.1	32859911
AllCCS	[M+Na]+	140.2	32859911
AllCCS	[M-H]-	267.3	32859911
AllCCS	[M+Na-2H]-	277.9	32859911
AllCCS	[M+HCOO]-	289.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bromomethane	CBr	863.1	Standard polar	33892256
Bromomethane	CBr	397.5	Standard non polar	33892256
Bromomethane	CBr	406.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Bromomethane EI-B (Non-derivatized)	splash10-0007-9000000000-745f8b23626d21db04f3	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Bromomethane EI-B (Non-derivatized)	splash10-0007-9000000000-745f8b23626d21db04f3	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromomethane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0007-9000000000-7942af0aaf6970a66f15	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromomethane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bromomethane GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0007-9000000000-169ac2e004c3655205b0	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 10V, Positive-QTOF	splash10-0006-9000000000-489f85dffd44526b6faf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 20V, Positive-QTOF	splash10-0006-9000000000-489f85dffd44526b6faf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 40V, Positive-QTOF	splash10-0006-9000000000-489f85dffd44526b6faf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 10V, Negative-QTOF	splash10-0006-9000000000-8cbdea03c774de7d15ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 20V, Negative-QTOF	splash10-0006-9000000000-8cbdea03c774de7d15ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 40V, Negative-QTOF	splash10-0006-9000000000-8cbdea03c774de7d15ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 10V, Positive-QTOF	splash10-0006-9000000000-7cb72c4b41f7b99ed261	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 20V, Positive-QTOF	splash10-0006-9000000000-7cb72c4b41f7b99ed261	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 40V, Positive-QTOF	splash10-0006-9000000000-7cb72c4b41f7b99ed261	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 10V, Negative-QTOF	splash10-0006-9000000000-e800a553de932a2e14db	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 20V, Negative-QTOF	splash10-0006-9000000000-e800a553de932a2e14db	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bromomethane 40V, Negative-QTOF	splash10-0006-9000000000-e800a553de932a2e14db	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Glutathione metabolism	Not Available
Glutathione Synthetase Deficiency		Not Available
5-Oxoprolinuria		Not Available
Gamma-Glutamyltransferase Deficiency		Not Available
5-oxoprolinase deficiency		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008126

KNApSAcK ID

Not Available

Chemspider ID

6083

KEGG Compound ID

C18447

BioCyc ID

CPD-12221

BiGG ID

Not Available

Wikipedia Link

Bromomethane

METLIN ID

Not Available

PubChem Compound

6323

PDB ID

BMM

ChEBI ID

39275

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1225721

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Zhao RS, Lao WJ, Xu XB: Headspace liquid-phase microextraction of trihalomethanes in drinking water and their gas chromatographic determination. Talanta. 2004 Mar 10;62(4):751-6. doi: 10.1016/j.talanta.2003.09.035. [PubMed:18969359 ]
Mouly D, Joulin E, Rosin C, Beaudeau P, Zeghnoun A, Olszewski-Ortar A, Munoz JF, Welte B, Joyeux M, Seux R, Montiel A, Rodriguez MJ: Variations in trihalomethane levels in three French water distribution systems and the development of a predictive model. Water Res. 2010 Oct;44(18):5168-79. doi: 10.1016/j.watres.2010.06.028. Epub 2010 Jun 19. [PubMed:20663536 ]
Graham EA: LATE POISONING WITH CHLOROFORM AND OTHER ALKYL HALIDES IN RELATIONSHIP TO THE HALOGEN ACIDS FORMED BY THEIR CHEMICAL DISSOCIATION. J Exp Med. 1915 Jul 1;22(1):48-75. [PubMed:19867902 ]
Langfermann C, Klementz D, Sierts-Herrmann A, Poschadel B, Sagunski H, Hosch C, Horn K, Reichmuth C, Baur X: [Study on the potential impact of bromomethane on medicinal products following simulated container fumigation]. Bundesgesundheitsblatt Gesundheitsforschung Gesundheitsschutz. 2007 Apr;50(4):492-9. [PubMed:17387439 ]
FREW WD: Rectal tribrom-ethanol (avertin, bromethol) in eclamptic toxaemia. Can Med Assoc J. 1953 Sep;69(3):254-7. [PubMed:13082465 ]
Catto C, Charest-Tardif G, Rodriguez M, Tardif R: Accounting for the impact of short-term variations in the levels of trihalomethane in drinking water on exposure assessment for epidemiological purposes. Part II: biological aspects. J Expo Sci Environ Epidemiol. 2013 Jan-Feb;23(1):60-6. doi: 10.1038/jes.2012.88. Epub 2012 Sep 12. [PubMed:22968351 ]
Wang GS, Deng YC, Lin TF: Cancer risk assessment from trihalomethanes in drinking water. Sci Total Environ. 2007 Nov 15;387(1-3):86-95. Epub 2007 Aug 28. [PubMed:17727920 ]
Narotsky MG, Best DS, McDonald A, Godin EA, Hunter ES 3rd, Simmons JE: Pregnancy loss and eye malformations in offspring of F344 rats following gestational exposure to mixtures of regulated trihalomethanes and haloacetic acids. Reprod Toxicol. 2011 Jan;31(1):59-65. doi: 10.1016/j.reprotox.2010.08.002. Epub 2010 Sep 17. [PubMed:20850520 ]
Rodrigues PM, Esteves da Silva JC, Antunes MC: Factorial analysis of the trihalomethanes formation in water disinfection using chlorine. Anal Chim Acta. 2007 Jul 9;595(1-2):266-74. Epub 2006 Dec 23. [PubMed:17606009 ]
Zsolnai T: [Tribrom-nitromethan--a new disinfectant of high efficiency (author's transl)]. Zentralbl Bakteriol Orig A. 1973 Oct;224(4):496-502. [PubMed:4150117 ]
Saghir SA, Ghanayem BI, Schultz IR: Kinetics of trihalogenated acetic acid metabolism and isoform specificity in liver microsomes. Int J Toxicol. 2011 Oct;30(5):551-61. doi: 10.1177/1091581811414213. Epub 2011 Sep 20. [PubMed:21933969 ]
Weaver WA, Li J, Wen Y, Johnston J, Blatchley MR, Blatchley ER 3rd: Volatile disinfection by-product analysis from chlorinated indoor swimming pools. Water Res. 2009 Jul;43(13):3308-18. doi: 10.1016/j.watres.2009.04.035. Epub 2009 May 3. [PubMed:19501873 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Bromomethane (HMDB0031524)

MOL for HMDB0031524 (Bromomethane)

3D MOL for HMDB0031524 (Bromomethane)

3D SDF for HMDB0031524 (Bromomethane)

3D-SDF for HMDB0031524 (Bromomethane)

PDB for HMDB0031524 (Bromomethane)

3D PDB for HMDB0031524 (Bromomethane)

SMILES for HMDB0031524 (Bromomethane)

INCHI for HMDB0031524 (Bromomethane)

Structure for HMDB0031524 (Bromomethane)

3D Structure for HMDB0031524 (Bromomethane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra