1-Bromopropane (T3D1802)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (4)XML
Targets (4)
Record Information
Version2.0
Creation Date2009-06-22 16:08:38 UTC
Update Date2014-12-24 20:24:39 UTC
Accession NumberT3D1802
Identification
Common Name1-Bromopropane
ClassSmall Molecule
Description1-bromopropane is an organobromide compound. It is a widely used organic solvent used for the cleaning of metal surfaces, removal of soldering residues from electronic circuit boards, and in the hole transport layer (HTL) of multi-layered OLEDs. It is also a solvent for adhesives and has been deployed as a replacement for perchloroethylene as a dry cleaning solvent. Its use as a solvent in aerosol glues used to glue foam cushions has been especially problematic. 1-bromopropane’s increasing use in the 21st century resulted from need for a substitute for chlorofluorocarbons and perchloroethylene (tetrachloroethylene). In 2013, a peer-review panel convened by the National Toxicology Program unanimously recommended that 1-bromopropane should be classified as a reasonably anticipated human carcinogen.
Compound Type
  • Bromide Compound
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Synonym
1-BROMO-PROPANE
Bromo propane
Bromopropane
n-C3H7Br
N-propyl bromide
Propyl bromide
Chemical FormulaC3H7Br
Average Molecular Mass122.992 g/mol
Monoisotopic Mass121.973 g/mol
CAS Registry Number106-94-5
IUPAC Name1-bromopropane
Traditional Name1-bromopropane
SMILESCCCBr
InChI IdentifierInChI=1S/C3H7Br/c1-2-3-4/h2-3H2,1H3
InChI KeyInChIKey=CYNYIHKIEHGYOZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as organobromides. Organobromides are compounds containing a chemical bond between a carbon atom and a bromine atom.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassOrganobromides
Sub ClassNot Available
Direct ParentOrganobromides
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organobromide
  • 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
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-110°C
Boiling PointNot Available
Solubility2.45 mg/mL at 20°C [YALKOWSKY,SH & HE,Y (2003)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.94 g/LALOGPS
logP2.18ALOGPS
logP1.9ChemAxon
logS-1.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity23.57 m³·mol⁻¹ChemAxon
Polarizability9.49 ųChemAxon
Number of Rings0ChemAxon
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, Positivesplash10-00di-0900000000-93ae8c951826e949031d2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-ab167994627595e931492016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-7b7d969d767e9487c0f52016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1900000000-e80db58d1fdc9666b6c22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3900000000-ac0f96881b04617b63322016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-303d9b4d82c8afc6ed072016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-01436ff6705673c9ce0e2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
Toxicity Profile
Route of ExposureOral (9) ; inhalation (9) ; dermal (9)
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. Alkylation of DNA by alkylbromides may also lead to mutations. 1-bromopropane reacts quickly with hepatic glutathione (GSH) leading to its rapid depletion and subsequent liver damage. Long-term exposure to 1-bromopropane decreases neurogenesis in the dentate gyrus which may contribute to the neurotoxicity. Downregulation of brain derived neurotrophic factor and glucocoritoid receptor mRNA expression and low hippocampal norepinephrine levels might contribute, at least in part, to the reduced neurogenesis.
Metabolism1-bromopropane is metabolized rapidly in the liver. Three mercapturic acids are produced: N-acetyl-S-propyl cysteine, N-acetyl-S-propyl cysteine-S-oxide and N-acetyl-S-(2-hydroxypropyl)cysteine. 1-bromopropoane also reacts rapidly with glutathione and can form glutathione conjugates.
Toxicity ValuesLD50: 2.5 g/kg (Intraperitoneal, Mouse) (5) LC50: 7000 ppm over 4 hours (Inhalation, Rat) (6)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesCleaning solvent, drycleaning solvent, aerosol glue solvent. 1-bromopropane may be found in products used in vapor and immersion degreasing operations for cleaning metal, plastics, electronic and optical components; in adhesive spray applications; and in dry cleaning operations. 1-bromopropane may also be a component of some aerosol spray products. Exposures to 1-bromopropane in occupational settings occur via two primary routes: (1) inhalation of 1-bromopropane vapors and mists; and (2) skin contact with 1-bromopropane.
Minimum Risk LevelNot Available
Health EffectsSkin irritation if contacts skin, redness and itching of skin and eyes. Acute exposure may lead to coughing, shortness of breath, headache, nausea, vomiting. Chronic exposure can lead to damage of the blood, liver and CNS. Neurotoxicity can arise due to chronic exposure through inhalation or skin. Human cases of 1-bromopropane (1-BP) toxicity exhibit ataxic gait and cognitive dysfunction, whereas rat studies showed pyknotic shrinkage in cerebellar Purkinje cells and electrophysiological changes in the hippocampus. Inhalation exposure to 1-bromopropane causes skin tumors in male rats, large intestine tumors in female and male rats, and lung tumors in female mice. 1-bromopropane, either directly or via reactive metabolites, can cause molecular alterations that typically are associated with carcinogenesis, including genotoxicity, oxidative stress, and glutathione depletion. Hepatotoxicity and reproductive toxicity have been noted in rodent studies.
SymptomsReported symptoms to overexposure include confusion, dysarthria, dizziness, paresthesias, and ataxia; unusual fatigue and headaches, development of arthralgias, visual disturbances (difficulty focusing), paresthesias, and muscular twitching. Symptoms may persist over one year after termination of exposure. Vapors may cause dizziness and suffocation. Inhalation of high concentrations may affect behavior/central nervous system (CNS depression) characterized by nausea, headache, dizziness, somnolence, unconsciousness and coma. It may also cause liver and kidney damage, lung injury, weight loss/ anorexia, bone marrow changes, and blood abnormalities.
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 ID7840
ChEMBL IDCHEMBL1230095
ChemSpider ID7552
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID47105
BioCyc IDBETA-AMINOPROPIONITRILE
CTD IDC118559
Stitch IDn-Propyl bromide
PDB IDNot Available
ACToR ID1811
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1802.pdf
General References
  1. Samukawa M, Ichihara G, Oka N, Kusunoki S: A case of severe neurotoxicity associated with exposure to 1-bromopropane, an alternative to ozone-depleting or global-warming solvents. Arch Intern Med. 2012 Sep 10;172(16):1257-60. doi: 10.1001/archinternmed.2012.3987. [22893012 ]
  2. Zhang L, Nagai T, Yamada K, Ibi D, Ichihara S, Subramanian K, Huang Z, Mohideen SS, Naito H, Ichihara G: Effects of sub-acute and sub-chronic inhalation of 1-bromopropane on neurogenesis in adult rats. Toxicology. 2013 Feb 8;304:76-82. doi: 10.1016/j.tox.2012.12.009. Epub 2012 Dec 21. [23266320 ]
  3. Liu F, Ichihara S, Valentine WM, Itoh K, Yamamoto M, Sheik Mohideen S, Kitoh J, Ichihara G: Increased susceptibility of Nrf2-null mice to 1-bromopropane-induced hepatotoxicity. Toxicol Sci. 2010 Jun;115(2):596-606. doi: 10.1093/toxsci/kfq075. Epub 2010 Mar 8. [20211940 ]
  4. Lee SK, Jeon TW, Kim YB, Lee ES, Jeong HG, Jeong TC: Role of glutathione conjugation in the hepatotoxicity and immunotoxicity induced by 1-bromopropane in female BALB/c mice. J Appl Toxicol. 2007 Jul-Aug;27(4):358-67. [17265426 ]
  5. Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  6. American Conference of Governmental Industrial Hygienists (2008). TLVs and BEIs. Threshold Limit Values for Chemical Substances and Physical Agents and Biological Exposure Indices. Cincinnati, OH: American Conference of Governmental Industrial Hygienists.
  7. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  8. Wikipedia. n-Propyl bromide. Last Updated 5 June 2009. bromide> [Link]
  9. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

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. Samukawa M, Ichihara G, Oka N, Kusunoki S: A case of severe neurotoxicity associated with exposure to 1-bromopropane, an alternative to ozone-depleting or global-warming solvents. Arch Intern Med. 2012 Sep 10;172(16):1257-60. doi: 10.1001/archinternmed.2012.3987. [22893012 ]
  2. Zhang L, Nagai T, Yamada K, Ibi D, Ichihara S, Subramanian K, Huang Z, Mohideen SS, Naito H, Ichihara G: Effects of sub-acute and sub-chronic inhalation of 1-bromopropane on neurogenesis in adult rats. Toxicology. 2013 Feb 8;304:76-82. doi: 10.1016/j.tox.2012.12.009. Epub 2012 Dec 21. [23266320 ]
  3. Liu F, Ichihara S, Valentine WM, Itoh K, Yamamoto M, Sheik Mohideen S, Kitoh J, Ichihara G: Increased susceptibility of Nrf2-null mice to 1-bromopropane-induced hepatotoxicity. Toxicol Sci. 2010 Jun;115(2):596-606. doi: 10.1093/toxsci/kfq075. Epub 2010 Mar 8. [20211940 ]
  4. Lee SK, Jeon TW, Kim YB, Lee ES, Jeong HG, Jeong TC: Role of glutathione conjugation in the hepatotoxicity and immunotoxicity induced by 1-bromopropane in female BALB/c mice. J Appl Toxicol. 2007 Jul-Aug;27(4):358-67. [17265426 ]
Target Details
2. Glutathione
References
  1. Samukawa M, Ichihara G, Oka N, Kusunoki S: A case of severe neurotoxicity associated with exposure to 1-bromopropane, an alternative to ozone-depleting or global-warming solvents. Arch Intern Med. 2012 Sep 10;172(16):1257-60. doi: 10.1001/archinternmed.2012.3987. [22893012 ]
  2. Zhang L, Nagai T, Yamada K, Ibi D, Ichihara S, Subramanian K, Huang Z, Mohideen SS, Naito H, Ichihara G: Effects of sub-acute and sub-chronic inhalation of 1-bromopropane on neurogenesis in adult rats. Toxicology. 2013 Feb 8;304:76-82. doi: 10.1016/j.tox.2012.12.009. Epub 2012 Dec 21. [23266320 ]
  3. Liu F, Ichihara S, Valentine WM, Itoh K, Yamamoto M, Sheik Mohideen S, Kitoh J, Ichihara G: Increased susceptibility of Nrf2-null mice to 1-bromopropane-induced hepatotoxicity. Toxicol Sci. 2010 Jun;115(2):596-606. doi: 10.1093/toxsci/kfq075. Epub 2010 Mar 8. [20211940 ]
  4. Lee SK, Jeon TW, Kim YB, Lee ES, Jeong HG, Jeong TC: Role of glutathione conjugation in the hepatotoxicity and immunotoxicity induced by 1-bromopropane in female BALB/c mice. J Appl Toxicol. 2007 Jul-Aug;27(4):358-67. [17265426 ]
Target Details
3. Nuclear factor NF-kappa-B p105 subunit
General Function:
Transcriptional repressor activity, rna polymerase ii transcription regulatory region sequence-specific binding
Specific Function:
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related to many biological processes such as inflammation, immunity, differentiation, cell growth, tumorigenesis and apoptosis. NF-kappa-B is a homo- or heterodimeric complex formed by the Rel-like domain-containing proteins RELA/p65, RELB, NFKB1/p105, NFKB1/p50, REL and NFKB2/p52 and the heterodimeric p65-p50 complex appears to be most abundant one. The dimers bind at kappa-B sites in the DNA of their target genes and the individual dimers have distinct preferences for different kappa-B sites that they can bind with distinguishable affinity and specificity. Different dimer combinations act as transcriptional activators or repressors, respectively. NF-kappa-B is controlled by various mechanisms of post-translational modification and subcellular compartmentalization as well as by interactions with other cofactors or corepressors. NF-kappa-B complexes are held in the cytoplasm in an inactive state complexed with members of the NF-kappa-B inhibitor (I-kappa-B) family. In a conventional activation pathway, I-kappa-B is phosphorylated by I-kappa-B kinases (IKKs) in response to different activators, subsequently degraded thus liberating the active NF-kappa-B complex which translocates to the nucleus. NF-kappa-B heterodimeric p65-p50 and RelB-p50 complexes are transcriptional activators. The NF-kappa-B p50-p50 homodimer is a transcriptional repressor, but can act as a transcriptional activator when associated with BCL3. NFKB1 appears to have dual functions such as cytoplasmic retention of attached NF-kappa-B proteins by p105 and generation of p50 by a cotranslational processing. The proteasome-mediated process ensures the production of both p50 and p105 and preserves their independent function, although processing of NFKB1/p105 also appears to occur post-translationally. p50 binds to the kappa-B consensus sequence 5'-GGRNNYYCC-3', located in the enhancer region of genes involved in immune response and acute phase reactions. In a complex with MAP3K8, NFKB1/p105 represses MAP3K8-induced MAPK signaling; active MAP3K8 is released by proteasome-dependent degradation of NFKB1/p105.
Gene Name:
NFKB1
Uniprot ID:
P19838
Molecular Weight:
105355.175 Da
References
  1. Samukawa M, Ichihara G, Oka N, Kusunoki S: A case of severe neurotoxicity associated with exposure to 1-bromopropane, an alternative to ozone-depleting or global-warming solvents. Arch Intern Med. 2012 Sep 10;172(16):1257-60. doi: 10.1001/archinternmed.2012.3987. [22893012 ]
  2. Zhang L, Nagai T, Yamada K, Ibi D, Ichihara S, Subramanian K, Huang Z, Mohideen SS, Naito H, Ichihara G: Effects of sub-acute and sub-chronic inhalation of 1-bromopropane on neurogenesis in adult rats. Toxicology. 2013 Feb 8;304:76-82. doi: 10.1016/j.tox.2012.12.009. Epub 2012 Dec 21. [23266320 ]
  3. Liu F, Ichihara S, Valentine WM, Itoh K, Yamamoto M, Sheik Mohideen S, Kitoh J, Ichihara G: Increased susceptibility of Nrf2-null mice to 1-bromopropane-induced hepatotoxicity. Toxicol Sci. 2010 Jun;115(2):596-606. doi: 10.1093/toxsci/kfq075. Epub 2010 Mar 8. [20211940 ]
  4. Lee SK, Jeon TW, Kim YB, Lee ES, Jeong HG, Jeong TC: Role of glutathione conjugation in the hepatotoxicity and immunotoxicity induced by 1-bromopropane in female BALB/c mice. J Appl Toxicol. 2007 Jul-Aug;27(4):358-67. [17265426 ]
Target Details
4. Transcription factor p65
General Function:
Ubiquitin protein ligase binding
Specific Function:
NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related to many biological processes such as inflammation, immunity, differentiation, cell growth, tumorigenesis and apoptosis. NF-kappa-B is a homo- or heterodimeric complex formed by the Rel-like domain-containing proteins RELA/p65, RELB, NFKB1/p105, NFKB1/p50, REL and NFKB2/p52 and the heterodimeric p65-p50 complex appears to be most abundant one. The dimers bind at kappa-B sites in the DNA of their target genes and the individual dimers have distinct preferences for different kappa-B sites that they can bind with distinguishable affinity and specificity. Different dimer combinations act as transcriptional activators or repressors, respectively. NF-kappa-B is controlled by various mechanisms of post-translational modification and subcellular compartmentalization as well as by interactions with other cofactors or corepressors. NF-kappa-B complexes are held in the cytoplasm in an inactive state complexed with members of the NF-kappa-B inhibitor (I-kappa-B) family. In a conventional activation pathway, I-kappa-B is phosphorylated by I-kappa-B kinases (IKKs) in response to different activators, subsequently degraded thus liberating the active NF-kappa-B complex which translocates to the nucleus. NF-kappa-B heterodimeric p65-p50 and p65-c-Rel complexes are transcriptional activators. The NF-kappa-B p65-p65 complex appears to be involved in invasin-mediated activation of IL-8 expression. The inhibitory effect of I-kappa-B upon NF-kappa-B the cytoplasm is exerted primarily through the interaction with p65. p65 shows a weak DNA-binding site which could contribute directly to DNA binding in the NF-kappa-B complex. Associates with chromatin at the NF-kappa-B promoter region via association with DDX1. Essential for cytokine gene expression in T-cells (PubMed:15790681).
Gene Name:
RELA
Uniprot ID:
Q04206
Molecular Weight:
60218.53 Da
References
  1. Samukawa M, Ichihara G, Oka N, Kusunoki S: A case of severe neurotoxicity associated with exposure to 1-bromopropane, an alternative to ozone-depleting or global-warming solvents. Arch Intern Med. 2012 Sep 10;172(16):1257-60. doi: 10.1001/archinternmed.2012.3987. [22893012 ]
  2. Zhang L, Nagai T, Yamada K, Ibi D, Ichihara S, Subramanian K, Huang Z, Mohideen SS, Naito H, Ichihara G: Effects of sub-acute and sub-chronic inhalation of 1-bromopropane on neurogenesis in adult rats. Toxicology. 2013 Feb 8;304:76-82. doi: 10.1016/j.tox.2012.12.009. Epub 2012 Dec 21. [23266320 ]
  3. Liu F, Ichihara S, Valentine WM, Itoh K, Yamamoto M, Sheik Mohideen S, Kitoh J, Ichihara G: Increased susceptibility of Nrf2-null mice to 1-bromopropane-induced hepatotoxicity. Toxicol Sci. 2010 Jun;115(2):596-606. doi: 10.1093/toxsci/kfq075. Epub 2010 Mar 8. [20211940 ]
  4. Lee SK, Jeon TW, Kim YB, Lee ES, Jeong HG, Jeong TC: Role of glutathione conjugation in the hepatotoxicity and immunotoxicity induced by 1-bromopropane in female BALB/c mice. J Appl Toxicol. 2007 Jul-Aug;27(4):358-67. [17265426 ]