T3DB: 3-Methylpentane

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (4)XML

Targets (4)

Record Information

Version

2.0

Creation Date

2009-06-30 20:55:29 UTC

Update Date

2014-12-24 20:25:27 UTC

Accession Number

T3D2405

Identification

Common Name

3-Methylpentane

Class

Small Molecule

Description

3-Methylpentane 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

MOL SDF PDB SMILES InChI

Synonyms

Synonym
3-Methyl-pentane
Diethylmethylmethane

Chemical Formula

C₆H₁₄

Average Molecular Mass

86.175 g/mol

Monoisotopic Mass

86.110 g/mol

CAS Registry Number

96-14-0

IUPAC Name

3-methylpentane

Traditional Name

3-methylpentane

SMILES

CCC(C)CC

InChI Identifier

InChI=1S/C6H14/c1-4-6(3)5-2/h6H,4-5H2,1-3H3

InChI Key

InChIKey=PFEOZHBOMNWTJB-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.

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Saturated hydrocarbons

Sub Class

Alkanes

Direct Parent

Branched alkanes

Alternative Parents

Not Available

Substituents

Branched alkane
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Liquid

Appearance

Colorless liquid.

Experimental Properties

Property	Value
Melting Point	-162.9°C
Boiling Point	Not Available
Solubility	0.0179 mg/mL at 25°C [YALKOWSKY,SH & HE,Y (2003)]
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.046 g/L	ALOGPS
logP	3.98	ALOGPS
logP	2.97	ChemAxon
logS	-3.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	29.36 m³·mol⁻¹	ChemAxon
Polarizability	12.02 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0adi-9000000000-6c96a5fdfe8ce4e77d24	2017-09-20	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-3060341393298519091f	2016-06-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9000000000-3ee52b2087c592bcdbee	2016-06-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-5a62157b5b53a2a73d4a	2016-06-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-c44d91f3b273433a3944	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-72fa4d8dca736350f1a6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-9000000000-aedb669ea13e77cf74a6	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-2dd044301debb5ba5b0e	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9000000000-85d388b4a3b345285ada	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-c536b9920e5efb2a572a	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9000000000-e58a231aeb9c5777eb4e	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-9000000000-9c082c87c22921d21b17	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-3fac9f5a185b1d631b98	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-ba2dfed9126ca7ea715d	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum

Toxicity Profile

Route of Exposure

Oral (3) ;inhalation (3) ;dermal (3)

Mechanism of Toxicity

Hexane'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)

Metabolism

Hexane 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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)

Minimum Risk Level

Chronic Inhalation: 0.6 ppm (2)

Health Effects

Hexane 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)

Symptoms

Breathing 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)

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

7282

ChEMBL ID

CHEMBL357767

ChemSpider ID

7010

KEGG ID

Not Available

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

CPD-285

CTD ID

C087331

Stitch ID

3-Methylpentane

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D2405.pdf

General References

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 ]
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]
Wikipedia. Methanol. Last Updated 19 May 2009. [Link]
Wikipedia. Hexane. Last Updated 15 June 2009. [Link]
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 Genes

Not Available

Down-Regulated Genes

Not 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

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

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

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

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 ]

3-Methylpentane (T3D2405)

Structure for T3D2405: 3-Methylpentane

Targets

References

References

References

References