ContaminantDB: Naphthalene

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (12)XML

Record Information

Version

1.0

Creation Date

2009-03-06 18:58:02 UTC

Update Date

2026-03-31 16:44:22 UTC

Accession Number

CHEM000074

Identification

Common Name

Naphthalene

Class

Small Molecule

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.

Contaminant Sources

Clean Air Act Chemicals
EAFUS Chemicals
FooDB Chemicals
HMDB Contaminants - Feces
HPV EPA Chemicals
IARC Carcinogens Group 2B
My Exposome Chemicals
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Aromatic Hydrocarbon
Food Toxin
Household Toxin
Industrial By-product/Pollutant
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
Pollutant
Polycyclic Aromatic Hydrocarbon

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Naftaleno	ChEBI
Naftalina	ChEBI
Naphtalene	ChEBI
Naphtaline	ChEBI
Naphthalen	ChEBI
Naphthalin	ChEBI
Albocarbon	HMDB
Camphor tar	HMDB
Moth balls	HMDB
Moth flakes	HMDB
Mothballs	HMDB
Naftalen	HMDB
Naphthaline	HMDB
Naphthene	HMDB
Tar camphor	HMDB
Tolboxane	HMDB
White tar	HMDB

Chemical Formula

C₁₀H₈

Average Molecular Mass

128.171 g/mol

Monoisotopic Mass

128.063 g/mol

CAS Registry Number

91-20-3

IUPAC Name

naphthalene

Traditional Name

naphthalene

SMILES

C1=CC2=CC=CC=C2C=C1

InChI Identifier

InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H

InChI Key

UFWIBTONFRDIAS-UHFFFAOYSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthalenes (CHEBI:16482 )
ortho-fused bicyclic arene (CHEBI:16482 )
Fumigants (C00829 )
an aromatic compound (NAPHTHALENE )

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

Chemical Roles

environmental contaminant

Physical Properties

State

Solid

Appearance

White crystals.

Experimental Properties

Property	Value
Melting Point	80.3°C
Boiling Point	218°C (424.4°F)
Solubility	0.031 mg/mL at 25°C

Predicted Properties

Property	Value	Source
Water Solubility	0.066 g/L	ALOGPS
logP	3.33	ALOGPS
logP	2.96	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	0	ChemAxon
Refractivity	42.51 m³·mol⁻¹	ChemAxon
Polarizability	14.56 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-28274068093bf0319e30	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-10810744223497787156	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-f640b15d5ebd285008e9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-2900000000-837afe39d2806871be73	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-262e4b8e72f3d3fa0593	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-3900000000-0e32d0a2d4bb6373bea3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-34ade0e20ab7aa4d4e7f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-c780f74ca6838fbab7d8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4900000000-b2e474b4d7508faeddc3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-7900000000-43781a61560faeff786d	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-0900000000-7a87251d344c519a4335	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-004i-0900000000-0532459557fd0c543587	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-004i-1900000000-5a22b095f0a190f1b978	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-28274068093bf0319e30	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-10810744223497787156	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-0900000000-f640b15d5ebd285008e9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-2900000000-837afe39d2806871be73	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-5900000000-262e4b8e72f3d3fa0593	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-3900000000-0e32d0a2d4bb6373bea3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-34ade0e20ab7aa4d4e7f	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-4900000000-c780f74ca6838fbab7d8	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-4900000000-b2e474b4d7508faeddc3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-7900000000-43781a61560faeff786d	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-0900000000-7a87251d344c519a4335	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-1900000000-35bf92cf7a210b27759b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-9058dd9b60d558e52773	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-9058dd9b60d558e52773	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1900000000-91e4df79f1f59e0c0465	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8575b97da509996b8151	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-8575b97da509996b8151	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-ff7fd755c09159064a33	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-71e8922109bea9aa624a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-6900000000-6558deffdb05b27a632e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-3900000000-f1f49df790d7f67edbc0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-004i-2900000000-1f03568d4331683921b4	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral (7); inhalation (7)

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.

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. (7)

Toxicity Values

LD50: 490 mg/kg (Oral, Rat) (12) LD50: >20 g/kg (Dermal, Rabbit) (12) LD50: 150 mg/kg (Intraperitoneal, Mouse) (11) LD50: 969 mg/kg (Subcutaneous, Mouse) (11) LD50: 100 mg/kg (Intravenous, Mouse) (11)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2B, possibly carcinogenic to humans. (10)

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.

Minimum Risk Level

Not Available

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.

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).

Treatment

There is no known antidote for PAHs. Exposure is usually handled with symptomatic treatment. (7)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0029751

FooDB ID

FDB000954

Phenol Explorer ID