1-Bromo-3-chloro-5,5-dimethylhydantoin (T3D1775)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (3)XML
Targets (3)
Record Information
Version2.0
Creation Date2009-06-22 16:08:35 UTC
Update Date2014-12-24 20:24:37 UTC
Accession NumberT3D1775
Identification
Common Name1-Bromo-3-chloro-5,5-dimethylhydantoin
ClassSmall Molecule
Description1-Bromo-3-chloro-5,5-dimethylhydantoin (BCDMH) is an organobromide compound. It is structurally related to hydantoin. It is a white crystalline compound with a slight bromine and acetone odor and is insoluble in water, but soluble in acetone. BCDMH is used as a solid halohydantion product for water disinfection and is an excellent source of both chlorine and bromine as it reacts slowly with water releasing hypochlorous acid and hypobromous acid along with 5,5-dimethylhydantion. It is primarily used as a chemical disinfectant for recreational water and drinking water purification. BCDMH was described as being responsible for an epidemic of irritant contact dermatitis in the UK (1983). It is prepared by first brominating, then chlorinating 5,5-dimethylhydantoin.
Compound Type
  • Amide
  • Household Toxin
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1-Bromo-3-chloro-5,5-dimethyl-2,4-imidazolidinedione
1-BROMO-3-CHLORO-5,5-DIMETHYLIMIDAZOLIDINE-2,4-DIONE
Agribrom
Di-halo
Halogene T 30
N-Bromo-N'-chloro-5,5-dimethylhydantoin
Slimicide 78P
Slimicide C 77P
Chemical FormulaC5H6BrClN2O2
Average Molecular Mass241.470 g/mol
Monoisotopic Mass239.930 g/mol
CAS Registry Number16079-88-2
IUPAC Name1-bromo-3-chloro-5,5-dimethylimidazolidine-2,4-dione
Traditional Namebcdmh
SMILESCC1(C)N(Br)C(=O)N(Cl)C1=O
InChI IdentifierInChI=1S/C5H6BrClN2O2/c1-5(2)3(10)8(7)4(11)9(5)6/h1-2H3
InChI KeyInChIKey=PIEXCQIOSMOEOU-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Alpha-amino acid or derivatives
  • Dicarboximide
  • Carbonic acid derivative
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
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 powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.71 g/LALOGPS
logP-0.96ALOGPS
logP1.23ChemAxon
logS-1.7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.52 m³·mol⁻¹ChemAxon
Polarizability17.48 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-d1df49a8979a0fc3c8a62016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0190000000-786a23e8da82f1b6cf292016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9440000000-ea61f9077059e57cb4fa2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f7ee03be3bb07af7e0f12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-961516cfeff08c632d662016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0300-3900000000-bcb95dabfc5f654497542016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral (7) ; inhalation (7) ; dermal (7)
Mechanism of ToxicityBCDMH likely causes tissue irritation through its breakdown products (hypochlorous acid and hypobromous acid) which, on their own, can cause local irritation. 5,5-dimethylhydantoin is also produced spontaneously from BCDMH decomposition and hydantoins are also known to be allergens.
MetabolismSpontaneously reacts with water releasing hypochlorous acid and hypobromous acid along with 5,5-dimethylhydantion.
Toxicity ValuesLD50: 1390 mg/kg (Oral, Rat) (4) LD50: >2000 mg/kg (Dermal, Rabbit) (4)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (8)
Uses/SourcesUsed as a solid halohydantion product for water disinfection in swimming pools. Occupational exposure to BCDMH may occur through inhalation and dermal contact with this compound at workplaces where BCDMH is produced or used.
Minimum Risk LevelNot Available
Health EffectsCorrosive. Acute exposure causes irreversible eye damage and skin burns. Eye contact may cause loss of vision. Irritating to nose and throat and may be fatal if large quantities are inhaled. Harmful if absorbed through skin or swallowed. Can cause contact dermatitis through exposure in swimming pools. It is not carcinogenic or mutagenic.
SymptomsIrritating to nose and throat. Can cause redness and itching of skin due to chronic skin exposure.
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 IDNot Available
HMDB IDNot Available
PubChem Compound ID61828
ChEMBL IDNot Available
ChemSpider ID55703
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC039283
Stitch ID1-Bromo-3-chloro-5,5-dimethylhydantoin
PDB IDNot Available
ACToR ID7870
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1775.pdf
General References
  1. Penny PT: Contact dermatitis due to BCDMH in a hydrotherapy pool. Occup Med (Lond). 1999 May;49(4):265-7. [10474922 ]
  2. Li W, Wei J, Jin H, Huang M, Zhang J, Li C, Chen C, Liu C, Wang A: Study of the toxicity of 1-Bromo-3-chloro-5,5-dimethylhydantoin to zebrafish. Biomed Environ Sci. 2011 Aug;24(4):383-90. doi: 10.3967/0895-3988.2011.04.009. [22108327 ]
  3. Dalmau G, Martinez-Escala ME, Gazquez V, Pujol-Montcusi JA, Canadell L, Espona Quer M, Pujol RM, Vilaplana J, Gaig P, Gimenez-Arnau A: Swimming pool contact dermatitis caused by 1-bromo-3-chloro-5,5-dimethyl hydantoin. Contact Dermatitis. 2012 Jun;66(6):335-9. doi: 10.1111/j.1600-0536.2012.02030.x. [22568840 ]
  4. Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
  5. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  6. Wikipedia. BCDMH. Last Updated 20 May 2009. [Link]
  7. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  8. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Estrogen receptor
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC509.02 uMACEA_T47D_80hr_PositiveACEA Biosciences
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
  3. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
Target Details
2. Transient receptor potential cation channel subfamily A member 1
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. Penny PT: Contact dermatitis due to BCDMH in a hydrotherapy pool. Occup Med (Lond). 1999 May;49(4):265-7. [10474922 ]
  2. Li W, Wei J, Jin H, Huang M, Zhang J, Li C, Chen C, Liu C, Wang A: Study of the toxicity of 1-Bromo-3-chloro-5,5-dimethylhydantoin to zebrafish. Biomed Environ Sci. 2011 Aug;24(4):383-90. doi: 10.3967/0895-3988.2011.04.009. [22108327 ]
  3. Dalmau G, Martinez-Escala ME, Gazquez V, Pujol-Montcusi JA, Canadell L, Espona Quer M, Pujol RM, Vilaplana J, Gaig P, Gimenez-Arnau A: Swimming pool contact dermatitis caused by 1-bromo-3-chloro-5,5-dimethyl hydantoin. Contact Dermatitis. 2012 Jun;66(6):335-9. doi: 10.1111/j.1600-0536.2012.02030.x. [22568840 ]
  4. Wikipedia. BCDMH. Last Updated 20 May 2009. [Link]
Target Details
3. Estrogen receptor beta
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Gene Name:
ESR2
Uniprot ID:
Q92731
Molecular Weight:
59215.765 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
  2. Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors α and β: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.