Tmic
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Record Information
Version2.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2014-12-24 20:24:37 UTC
Accession NumberT3D1777
Identification
Common NameBromoacetic acid
ClassSmall Molecule
DescriptionBromoacetic acid is an organobromide compound. It is an alkylating agent used primarily as a chemical intermediate in various organic syntheses. Bromoacetic acid and its esters are widely used building blocks in organic synthesis, for example in the pharmaceutical chemistry. Bromoacetic acid is also produced as a by-product through drinking water disinfection.
Compound Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
.alpha.-bromoacetic acid
2-Bromoacetic acid
a-Bromoacetic acid
a-Bromoethanoic acid
Acetic acid, bromo-, (solution)
Acide bromacetique
BRM
Bromo-acetic acid
Bromoacetate
Bromoacetate ion
Bromoacetic acid (acd/name 4.0)
Bromoacetic acid solution
Bromoacetic acid solution (dot)
Bromoacetic acid, pract
Bromoacetic acid, solid
Bromoacetic acid, solid (dot)
Bromoacetic acid, solution
Bromoethanoic acid
CH2BrCOOH
Kyselina bromoctova
Monobromessigsaeure
Monobromoacetic acid
Chemical FormulaC2H3BrO2
Average Molecular Mass138.948 g/mol
Monoisotopic Mass137.932 g/mol
CAS Registry Number79-08-3
IUPAC Name2-bromoacetic acid
Traditional Nameto ntu
SMILESOC(=O)CBr
InChI IdentifierInChI=1S/C2H3BrO2/c3-1-2(4)5/h1H2,(H,4,5)
InChI KeyInChIKey=KDPAWGWELVVRCH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha-halocarboxylic acids. These are carboxylic acids containing a halogen atom bonded to the alpha carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAlpha-halocarboxylic acids and derivatives
Direct ParentAlpha-halocarboxylic acids
Alternative Parents
Substituents
  • Alpha-halocarboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organobromide
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl bromide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite to pale yellow crystals.
Experimental Properties
PropertyValue
Melting Point50°C
Boiling Point206 - 208°C
Solubility1750 mg/mL at 25°C [BOWDEN,DJ et al. (1998A)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility107 g/LALOGPS
logP0.53ALOGPS
logP0.5ChemAxon
logS-0.11ALOGPS
pKa (Strongest Acidic)2.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.38 m³·mol⁻¹ChemAxon
Polarizability8.39 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-0f29157733f334c58af7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-65083568b781ed35c83aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-2900000000-5672959e96eba9a58497View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-c49a481e327eca2f6d13View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-b36c446c2f08c51169beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-1900000000-bba1d1be8e1fc8a66b09View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0007-9100000000-2f67f020965bfe36eaffView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6) ; dermal (6)
Mechanism of ToxicityOrganobromide compounds, especially alkylbromides are strong alkylating agents. Consequently they can randomly modify the surfaces of proteins and lipids, leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs. Alkylation of DNA by organobromides may also lead to mutations.
MetabolismNot Available
Toxicity ValuesLD50: 177 mg/kg (Oral, Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesBromoacetici acid is an industrial and laboratory chemical. It is produced as a drinking water disinfection by-product and small amounts may be found in treated drinking water.
Minimum Risk LevelNot Available
Health EffectsBromoacetic acid is a strong lachrymator. Animal studies have also indicated that bromoacetic acid is a teratogen (a developmental toxin) leading to soft tissue malformations in fetuses at doses of 100 mg/kg/day. Bromoacetic acid is also a mutagen and a cytotoxic agent.
SymptomsContact can lead to severe skin and eye burns, it can also irritate the nose throat and lungs if inhaled. Inhalation may result in spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin.
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB02198
HMDB IDNot Available
PubChem Compound ID6227
ChEMBL IDCHEMBL60851
ChemSpider ID10301338
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDBromoacetic acid
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1777.pdf
General References
  1. Quadro L, Hamberger L, Gottesman ME, Wang F, Colantuoni V, Blaner WS, Mendelsohn CL: Pathways of vitamin A delivery to the embryo: insights from a new tunable model of embryonic vitamin A deficiency. Endocrinology. 2005 Oct;146(10):4479-90. Epub 2005 Jun 30. [15994349 ]
  2. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  3. International Programme on Chemical Safety (IPCS) (1999). Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products. IPCS under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization.
  4. Wikipedia. Bromoacetic acid. Last Updated 20 February 2009. [Link]
  5. Bromoacetic Acid [Link]
  6. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Kargalioglu Y, McMillan BJ, Minear RA, Plewa MJ: Analysis of the cytotoxicity and mutagenicity of drinking water disinfection by-products in Salmonella typhimurium. Teratog Carcinog Mutagen. 2002;22(2):113-28. [11835289 ]
  2. International Programme on Chemical Safety (IPCS) (1999). Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products. IPCS under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization.
  3. Wikipedia. Bromoacetic acid. Last Updated 20 February 2009. [Link]
References
  1. Kargalioglu Y, McMillan BJ, Minear RA, Plewa MJ: Analysis of the cytotoxicity and mutagenicity of drinking water disinfection by-products in Salmonella typhimurium. Teratog Carcinog Mutagen. 2002;22(2):113-28. [11835289 ]
  2. International Programme on Chemical Safety (IPCS) (1999). Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products. IPCS under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization.
  3. Wikipedia. Bromoacetic acid. Last Updated 20 February 2009. [Link]
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
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. Kargalioglu Y, McMillan BJ, Minear RA, Plewa MJ: Analysis of the cytotoxicity and mutagenicity of drinking water disinfection by-products in Salmonella typhimurium. Teratog Carcinog Mutagen. 2002;22(2):113-28. [11835289 ]
  2. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
  3. International Programme on Chemical Safety (IPCS) (1999). Environmental Health Criteria 216: Disinfectants and DIsinfectant By-Products. IPCS under the joint sponsorship of the United Nations Environment Programme, the International Labour Organisation and the World Health Organization.
  4. Wikipedia. Bromoacetic acid. Last Updated 20 February 2009. [Link]
General Function:
Zinc ion binding
Specific Function:
Tyrosine-protein phosphatase which acts as a regulator of endoplasmic reticulum unfolded protein response. Mediates dephosphorylation of EIF2AK3/PERK; inactivating the protein kinase activity of EIF2AK3/PERK. May play an important role in CKII- and p60c-src-induced signal transduction cascades. May regulate the EFNA5-EPHA3 signaling pathway which modulates cell reorganization and cell-cell repulsion. May also regulate the hepatocyte growth factor receptor signaling pathway through dephosphorylation of MET.
Gene Name:
PTPN1
Uniprot ID:
P18031
Molecular Weight:
49966.44 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory77000 uMNot AvailableBindingDB 50119693
References
  1. Arabaci G, Yi T, Fu H, Porter ME, Beebe KD, Pei D: alpha-bromoacetophenone derivatives as neutral protein tyrosine phosphatase inhibitors: structure-Activity relationship. Bioorg Med Chem Lett. 2002 Nov 4;12(21):3047-50. [12372498 ]