2,3-Dimethylbutane (T3D2406)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (4)XML
Targets (4)
Record Information
Version2.0
Creation Date2009-06-30 20:56:10 UTC
Update Date2014-12-24 20:25:27 UTC
Accession NumberT3D2406
Identification
Common Name2,3-Dimethylbutane
ClassSmall Molecule
Description2,3-Dimethylbutane is an isomer of hexane. Hexane is a chemical made from crude oil. It is highly flammable, and its vapors can be explosive. Pure hexane is used in laboratories. Most of the hexane used in industry is mixed with similar chemicals called solvents. The major use for solvents containing hexane is to extract vegetable oils from crops such as soybeans. These solvents are also used as cleaning agents in the printing, textile, furniture, and shoemaking industries. Certain kinds of special glues used in the roofing and shoe and leather industries also contain hexane. Several consumer products contain hexane, such as gasoline, quick-drying glues used in various hobbies, and rubber cement. (3)
Compound Type
  • Gasoline Additive/Component
  • Industrial/Workplace Toxin
  • Organic Compound
  • Solvent
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1,1,2,2-Tetramethylethane
BIIsopropyl
DIIsopropyl
Chemical FormulaC6H14
Average Molecular Mass86.175 g/mol
Monoisotopic Mass86.110 g/mol
CAS Registry Number79-29-8
IUPAC Name2,3-dimethylbutane
Traditional Name2,3-dimethylbutane
SMILESCC(C)C(C)C
InChI IdentifierInChI=1S/C6H14/c1-5(2)6(3)4/h5-6H,1-4H3
InChI KeyInChIKey=ZFFMLCVRJBZUDZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassSaturated hydrocarbons
Sub ClassAlkanes
Direct ParentBranched alkanes
Alternative ParentsNot Available
Substituents
  • Branched alkane
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceColorless liquid.
Experimental Properties
PropertyValue
Melting Point-128.8°C
Boiling PointNot Available
Solubility0.0225 mg/mL at 25°C [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.09 g/LALOGPS
logP2.84ALOGPS
logP2.82ChemAxon
logS-3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.3 m³·mol⁻¹ChemAxon
Polarizability11.93 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-58486198412c95c731cd2021-09-24View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-f805f2615e9ff2431a6f2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9000000000-a140c6c0bab8e56126062016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9000000000-034231edfb8bc90830b72016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-e11dbf08fbcd9e42fbdc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-e11dbf08fbcd9e42fbdc2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-e5907960c7db3c2c285e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-9000000000-0dc0cdafa45af6c0ba582021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-9000000000-c083355edc40c6efdcc32021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-efed8ae6ab12612314192021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-2dd044301debb5ba5b0e2021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-a6a07d934d6d5ea59da82021-10-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-923ad8786d1d8cce5cac2021-10-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-6b25ca8220372c61d4812014-09-20View 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 (3) ;inhalation (3) ;dermal (3)
Mechanism of ToxicityHexane's toxicity is caused by it neurotoxic metabolite, 2,5-hexanedione. It damages the central and peripheral nervous system by causing axonal swelling and degeneration. 2,5-Hexanedione also reacts with lysine side-chain amino groups in axonal cytoskeletal proteins to form pyrroles. This results in neurofilament cross-linking and loss of function. (3)
MetabolismHexane is mainly absorbed via inhalation, as it is readily absorbed by the lungs. It is distributed throughout the body in the blood, and metabolized by mixed function oxidases in the liver to a number of metabolites. The initial reaction is oxidation by cytochrome P-450 isozymes to hexanols, predominantly 2-hexanol. Further reactions convert 2-hexanol to 2-hexanone, 2,5-hexanediol, 5-hydroxy-2-hexanone, 4,5-dihydroxy-2-hexanone and the neurotoxicant 2,5-hexanedione. Hexane metabolites are excreted in the urine, while unchanged hexane is excreted in expired air. (3)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesPure hexane is used in laboratories. Most of the hexane used in industry is mixed with similar chemicals called solvents. The major use for solvents containing hexane is to extract vegetable oils from crops such as soybeans. These solvents are also used as cleaning agents in the printing, textile, furniture, and shoemaking industries. Certain kinds of special glues used in the roofing and shoe and leather industries also contain hexane. Several consumer products contain hexane, such as gasoline, quick-drying glues used in various hobbies, and rubber cement. (3)
Minimum Risk LevelChronic Inhalation: 0.6 ppm (2)
Health EffectsHexane mainly affects the nervous system. It causes degeneration of the peripheral nervous system (and eventually the central nervous system), starting with damage to the nerve axons. Exposure to hexane may also damage the lungs and reproductive system. (4, 5)
SymptomsBreathing large amounts of hexane causes numbness in the feet and hands, followed by muscle weakness in the feet and lower legs. Continued exposure may lead to paralysis of the arms and legs. However, if removed from the exposure, recovery occurs in 6 months to a year. Inhalation of high concentrations produces first a state of mild euphoria, followed by somnolence with headaches and nausea. (3, 1)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6589
ChEMBL IDCHEMBL1344453
ChemSpider ID6340
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDCPD-622
CTD IDC094658
Stitch ID2,3-Dimethylbutane
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D2406.pdf
General References
  1. Meulenberg CJ, Vijverberg HP: Selective inhibition of gamma-aminobutyric acid type A receptors in human IMR-32 cells by low concentrations of toluene. Toxicology. 2003 Aug 28;190(3):243-8. [12927378 ]
  2. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  3. Wikipedia. Methanol. Last Updated 19 May 2009. [Link]
  4. Wikipedia. Hexane. Last Updated 15 June 2009. [Link]
  5. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for n-hexane. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Myelin basic protein
General Function:
Structural constituent of myelin sheath
Specific Function:
The classic group of MBP isoforms (isoform 4-isoform 14) are with PLP the most abundant protein components of the myelin membrane in the CNS. They have a role in both its formation and stabilization. The smaller isoforms might have an important role in remyelination of denuded axons in multiple sclerosis. The non-classic group of MBP isoforms (isoform 1-isoform 3/Golli-MBPs) may preferentially have a role in the early developing brain long before myelination, maybe as components of transcriptional complexes, and may also be involved in signaling pathways in T-cells and neural cells. Differential splicing events combined with optional post-translational modifications give a wide spectrum of isomers, with each of them potentially having a specialized function. Induces T-cell proliferation.
Gene Name:
MBP
Uniprot ID:
P02686
Molecular Weight:
33116.855 Da
References
  1. Bale AS, Smothers CT, Woodward JJ: Inhibition of neuronal nicotinic acetylcholine receptors by the abused solvent, toluene. Br J Pharmacol. 2002 Oct;137(3):375-83. [12237258 ]
Target Details
2. Neurofilament heavy polypeptide
General Function:
Toxic substance binding
Specific Function:
Neurofilaments usually contain three intermediate filament proteins: L, M, and H which are involved in the maintenance of neuronal caliber. NF-H has an important function in mature axons that is not subserved by the two smaller NF proteins.
Gene Name:
NEFH
Uniprot ID:
P12036
Molecular Weight:
112477.915 Da
References
  1. Bale AS, Smothers CT, Woodward JJ: Inhibition of neuronal nicotinic acetylcholine receptors by the abused solvent, toluene. Br J Pharmacol. 2002 Oct;137(3):375-83. [12237258 ]
Target Details
3. Neurofilament light polypeptide
General Function:
Structural constituent of cytoskeleton
Specific Function:
Neurofilaments usually contain three intermediate filament proteins: L, M, and H which are involved in the maintenance of neuronal caliber.
Gene Name:
NEFL
Uniprot ID:
P07196
Molecular Weight:
61515.95 Da
References
  1. Bale AS, Smothers CT, Woodward JJ: Inhibition of neuronal nicotinic acetylcholine receptors by the abused solvent, toluene. Br J Pharmacol. 2002 Oct;137(3):375-83. [12237258 ]
Target Details
4. Neurofilament medium polypeptide
General Function:
Structural constituent of cytoskeleton
Specific Function:
Neurofilaments usually contain three intermediate filament proteins: L, M, and H which are involved in the maintenance of neuronal caliber.
Gene Name:
NEFM
Uniprot ID:
P07197
Molecular Weight:
102471.425 Da
References
  1. Bale AS, Smothers CT, Woodward JJ: Inhibition of neuronal nicotinic acetylcholine receptors by the abused solvent, toluene. Br J Pharmacol. 2002 Oct;137(3):375-83. [12237258 ]