Please note that T3DB is currently undergoing changes to improve data quality and
website features. You can access the original version of T3DB
here.
T3D0158 - 2-Methylnaphthalene
| Record Information | |
|---|---|
| Version | 1.0 |
| Creation Date | 2009-03-06 18:58:11 UTC |
| Update Date | 2013-04-25 08:33:05 UTC |
| Accession Number | T3D0158 |
| Identification | |
| Common Name | 2-Methylnaphthalene |
| Description | 2-Methylnaphthalene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs). PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels. They are usually found as a mixture containing two or more of these compounds. (R028) |
| Compound Type |
|
| Chemical Structure |
|
| Synonyms |
|
| Chemical Formula | C11H10 |
| Average Molecular Weight | 142.1971 |
| Monoisotopic Molecular Weight | 142.07825032 |
| Chemical IUPAC Name | 2-methylnaphthalene |
| CAS Registry Number | 91-57-6 |
| SMILES | CC1=CC=C2C=CC=CC2=C1 |
| InChI Identifier | InChI=1S/C11H10/c1-9-6-7-10-4-2-3-5-11(10)8-9/h2-8H,1H3 |
| InChI Key | InChIKey=QIMMUPPBPVKWKM-UHFFFAOYSA-N |
| Chemical Taxonomy | |
| Kingdom | Organic Compounds |
| Super Class | Benzenoids |
| Class | Acenes and Derivatives |
| Sub Class | Naphthalenes |
| Direct Parent | Naphthalenes |
| Alternative Parents |
|
| Molecular Framework | Aromatic Homopolycyclic Compounds |
| Substituents |
|
| External Descriptors |
|
| External Links | |
| DrugBank ID | Not Available |
| PubChem Compound ID | 7055  |
| KEGG ID | C14098 |
| UniProt ID | Not Available |
| OMIM ID | Not Available |
| ChEBI ID | 50720 |
| BioCyc ID | ALPHA-NAPHTHALENEACETAMIDE |
| CTD ID | C027384 |
| Stitch ID | 2-Methylnaphthalene |
| PDB ID | Not Available |
| ACToR ID | 898 |
| Wikipedia Link | Not Available |
| Physical Properties | |
| Appearance | White solid. |
| Melting Point | 34.4 C |
| Solubility | 0.0246 mg/mL at 25 °C [YALKOWSKY,SH & DANNENFELSER,RM (1992)] |
| Predicted LogP | 3.476143962 |
| Toxicity Profile | |
| Route of Exposure | Oral (R028) ; inhalation (R028) |
| Mechanism of Action | The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (R028, R060, R068, R073) |
| Metabolism | PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (R028) |
| Toxicity Values | LD50: 1630 mg/kg (Oral, Rat) (R263) |
| Lethal Dose | Not Available |
| Carcinogenicity (IARC Classification) | Not Available |
| Uses/Sources | PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and voLcanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. 2-Methylnaphthalene is used to make other chemicals such as dyes and resins. (R028, R035) |
| Minimum Risk Level | Not Available |
| Health Effects | PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. Exposure to large amounts of 2-methylnapthalene may damage or destroy the red blood cells, resulting in hemolytic anemia. (R028, R035) |
| Symptoms | Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. Some symptoms of hemolytic anemia are fatigue, lack of appetite, restlessness, and pale skin. Exposure to large amounts of 2-methylnapthalene may also cause nausea, vomiting, diarrhea, blood in the urine, and a yellow color to the skin. (R034, R035) |
| Treatment | There is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (R028) |
| References | |
| General References |
|
Targets
1. Aryl hydrocarbon receptor
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues.
Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (R028, R060, R068, R073)UniProt ID: P35869
Gene: AHR
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- R028 — ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- R060 — Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
- R068 — Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12.
[17997381 ]
- R073 — Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51.
[11460716 ]
2. Glycine N-methyltransferase
Catalyzes the methylation of glycine by using S-adenosylmethionine (AdoMet) to form N-methylglycine (sarcosine) with the concomitant production of S-adenosylhomocysteine (AdoHcy). Possible crucial role in the regulation of tissue concentration of AdoMet and of metabolism of methionine.
Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (R028, R060, R068, R073)UniProt ID: Q14749
Gene: GNMT
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- R028 — ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- R060 — Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
- R068 — Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12.
[17997381 ]
- R073 — Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51.
[11460716 ]
3. Cytokine receptor common subunit beta
High affinity receptor for interleukin-3, interleukin-5 and granulocyte-macrophage colony-stimulating factor.
The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (R028, R060, R068, R073)UniProt ID: P32927
Gene: CSF2RB
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- R028 — ATSDR - Agency for Toxic Substances and Disease Registry (1995). Toxicological profile for PAHs. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- R060 — Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
- R068 — Uno S, Dragin N, Miller ML, Dalton TP, Gonzalez FJ, Nebert DW: Basal and inducible CYP1 mRNA quantitation and protein localization throughout the mouse gastrointestinal tract. Free Radic Biol Med. 2008 Feb 15;44(4):570-83. Epub 2007 Nov 12.
[17997381 ]
- R073 — Padros J, Pelletier E: In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish. Mar Environ Res. 2000 Jul-Dec;50(1-5):347-51.
[11460716 ]