| Record Information |
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| Version | 2.0 |
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| Creation Date | 2009-03-06 18:58:02 UTC |
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| Update Date | 2014-12-24 20:21:03 UTC |
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| Accession Number | T3D0078 |
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| Identification |
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| Common Name | Naphthalene |
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| Class | Small Molecule |
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| Description | Naphthalene is the simplest polyaromatic hydrocarbon (PAH) consisting of two fused benzene rings. It has a distinct, pungent odor that can be detected at levels as low as 0.08 ppm. Naphthalene is the most abundant single component of coal tar so most of it is now industrially derived from coal tar. From the 1960s until the 1990s, significant amounts of naphthalene were also produced from heavy petroleum fractions during petroleum refining, but today petroleum-derived naphthalene represents only a minor component of naphthalene production. Naphthalene is also produced naturally with trace amounts of naphthalene being produced by black walnuts, magnolias and specific types of deer, as well as the Formosan subterranean termite. Some strains of the endophytic fungus (Muscodor albus) also produce naphthalene. Naphthalene and other polycyclic aromatic hydrocarbons (PAHs) are released from incomplete combustion processes originating in industry, cigarette smoke and motor vehicle exhaust, as well as natural events such as forest fires. Industrially, naphthalene is used in the production of phthalic anhydride, as a solvent for chemical reactions, as a wetting agent and as a fumigant. It is also used in pyrotechnic special effects such as the generation of black smoke and simulated explosions. In the past, naphthalene was administered orally to kill parasitic worms in livestock. Naphthalene was once the primary ingredient in mothballs, though its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. In a sealed container containing naphthalene pellets, naphthalene vapors build up to levels that are toxic to both the adult and larval forms of many moths. Naphthalene has been shown to exhibit apoptotic and catabolic functions (4, 5). Exposure to large amounts of naphthalene may damage or destroy red blood cells. Humans, in particular children, have developed this condition, known as hemolytic anemia, after ingesting mothballs or deodorant blocks containing naphthalene. |
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| Compound Type | - Aromatic Hydrocarbon
- Food Toxin
- Household Toxin
- Industrial By-product/Pollutant
- Industrial/Workplace Toxin
- Metabolite
- Natural Compound
- Organic Compound
- Pollutant
- Polycyclic Aromatic Hydrocarbon
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| Chemical Structure | |
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| Synonyms | | Synonym | | Albocarbon | | Camphor tar | | Moth balls | | Moth flakes | | Mothballs | | Naftalen | | Naphtalene | | Naphthalin | | Naphthaline | | Naphthene | | Tar camphor | | Tolboxane | | White tar |
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| Chemical Formula | C10H8 |
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| Average Molecular Mass | 128.171 g/mol |
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| Monoisotopic Mass | 128.063 g/mol |
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| CAS Registry Number | 91-20-3 |
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| IUPAC Name | naphthalene |
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| Traditional Name | naphthalene |
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| SMILES | C1=CC2=CC=CC=C2C=C1 |
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| InChI Identifier | InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H |
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| InChI Key | InChIKey=UFWIBTONFRDIAS-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Naphthalenes |
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| Sub Class | Not Available |
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| Direct Parent | Naphthalenes |
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| Alternative Parents | |
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| Substituents | - Naphthalene
- Aromatic hydrocarbon
- Polycyclic hydrocarbon
- Unsaturated hydrocarbon
- Hydrocarbon
- Aromatic homopolycyclic compound
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| Molecular Framework | Aromatic homopolycyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | |
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| Chemical Roles | |
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| Physical Properties |
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| State | Solid |
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| Appearance | White crystals. |
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| Experimental Properties | | Property | Value |
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| Melting Point | 80.3°C | | Boiling Point | 218°C (424.4°F) | | Solubility | 0.031 mg/mL at 25°C | | LogP | 3.3 |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Toxicity Profile |
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| Route of Exposure | Oral (10); inhalation (10) |
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| Mechanism of Toxicity | PAH's such as naphthalene are transported throughout the body after binding blood proteins such as albumin. Binding to the aryl hydrocarbon receptor or glycine N-methyltransferase induces the expression of cytochrome P450 enzymes (especially CYP1A1, CYP1A2, and CYP1B1). These cytochrome enzymes metabolize PAH's into various toxic intermediates (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations). The reactive metabolites of PAHs covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (10, 12, 2, 3). In humans, the metabolite alpha-naphthol has been linked to the development of hemolytic anemia in some cases following ingestion or extensive dermal or inhalation exposure. Susceptibility appears to be exacerbated by a deficiency in the glucose 6-phosphate dehydrogenase enzyme, or G-6-PD. Over 400 million people have an inherited condition called glucose-6-phosphate dehydrogenase deficiency. Exposure to naphthalene is more harmful for these people and may cause hemolytic anemia at lower doses. Some naphthalene metabolites deplete glutathione stores in affected tissues such as the lungs, leading to toxicity. The metabolites responsible for glutathione depletion have been identified as naphthalene oxide or 1,2-naphthoquinone and 1,4-naphthoquinone. |
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| 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 be conjugated to glucuronides and sulfate esters; and the quinones can form glutathione conjugates. (10) |
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| Toxicity Values | LD50: 490 mg/kg (Oral, Rat) (8)
LD50: >20 g/kg (Dermal, Rabbit) (8)
LD50: 150 mg/kg (Intraperitoneal, Mouse) (7)
LD50: 969 mg/kg (Subcutaneous, Mouse) (7)
LD50: 100 mg/kg (Intravenous, Mouse) (7) |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | 2B, possibly carcinogenic to humans. (13) |
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| Uses/Sources | Industrially, naphthalene is used in the production of phthalic anhydride, as a solvent for chemical reactions, as a wetting agent and as a fumigant. Naphthalene is produced industrially via coal tar and naturally with trace amounts of naphthalene being produced by black walnuts, magnolias and specific types of deer. |
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| Minimum Risk Level | Not Available |
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| Health Effects | Inhalation of naphthalene vapor has been associated with headaches, nausea, vomiting and dizziness. Hemolysis, the abnormal breakdown of red blood cells, may occur following ingestion or sufficient dermal exposure to either naphthalene or to naphthalene-treated fabric. In humans, cataracts and other ocular injury have been reported following acute and chronic occupational exposure to naphthalene. Additional signs of toxicity in children include convulsions and coma. Infants may develop encephalopathy and kernicterus, a form of brain damage, due to the presence of increased levels of methemoglobin, hemoglobin, and bilirubin in their plasma. Naphthalene appears to be mildly carcinogenic. Rats exposed to naphthalene vapors at 10, 30, or 60 ppm for 6 hours a day, five days a week for two years developed respiratory epithelial adenomas and olfactory epithelial neuroblastomas. |
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| Symptoms | Symptoms of hemolytic anemia include fatigue, lack of appetite, restlessness, and pale skin. Exposure to large amounts of naphthalene may cause confusion, nausea, vomiting, diarrhea, blood in the urine, and jaundice (yellow coloration of the skin). |
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| Treatment | There is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (10) |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB29751 |
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| PubChem Compound ID | 931 |
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| ChEMBL ID | CHEMBL16293 |
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| ChemSpider ID | 906 |
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| KEGG ID | C00829 |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | 16482 |
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| BioCyc ID | ALPHA-NAPHTHALENEACETAMIDE |
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| CTD ID | C031721 |
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| Stitch ID | Naphthalene |
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| PDB ID | NPY |
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| ACToR ID | 934 |
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| Wikipedia Link | Naphthalene |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Link |
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| General References | - Santodonato J, Howard P, Basu D: Health and ecological assessment of polynuclear aromatic hydrocarbons. J Environ Pathol Toxicol. 1981 Sep;5(1):1-364. [7310260 ]
- 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 ]
- 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 ]
- Pandya U, Saini MK, Jin GF, Awasthi S, Godley BF, Awasthi YC: Dietary curcumin prevents ocular toxicity of naphthalene in rats. Toxicol Lett. 2000 Jun 5;115(3):195-204. [10814889 ]
- Yen KM, Serdar CM: Genetics of naphthalene catabolism in pseudomonads. Crit Rev Microbiol. 1988;15(3):247-68. [3288442 ]
- Waidyanatha S, Zheng Y, Serdar B, Rappaport SM: Albumin adducts of naphthalene metabolites as biomarkers of exposure to polycyclic aromatic hydrocarbons. Cancer Epidemiol Biomarkers Prev. 2004 Jan;13(1):117-24. [14744742 ]
- Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold.
- Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
- Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
- 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]
- ATSDR - Agency for Toxic Substances and Disease Registry (2005). Toxicological profile for naphthalene, 1-methylnaphthalene, and 2-methyl-naphthalene. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
- Wikipedia. Benzopyrene. Last Updated 22 January 2009. [Link]
- International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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| Down-Regulated Genes | | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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