U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H8
Molecular Weight 128.1705
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NAPHTHALENE

SMILES

C1=CC2=C(C=C1)C=CC=C2

InChI

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

HIDE SMILES / InChI

Molecular Formula C10H8
Molecular Weight 128.1705
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: DOI: 10.1007/978-0-387-30160-0_7643 http://npic.orst.edu/factsheets/naphgen.html http://www.cdc.gov/niosh/npg/npgd0439.html

Naphthalene is a crystalline aromatic hydrocarbon usually obtained by distillation of coal tar. Once used as a moth repellent, it is now important as a reactant in the production of phthalic anhydride, which in turn is used for making plasticizers, alkyd resins, and polyester resins. Other fumigant uses of naphthalene include use in soil as a fumigant pesticide, and in attic spaces to repel animals. In the past, naphthalene was administered orally to kill parasitic worms in livestock. In humans, exposure to large amounts of naphthalene may damage or destroy red blood cells. Humans, particularly children, have developed this condition after ingesting mothballs or deodorant blocks containing naphthalene. Some of the symptoms of naphthalene poisoning are fatigue, lack of appetite, restlessness, and pale skin. Exposure to large amounts of naphthalene may also cause nausea, vomiting, diarrhea, blood in the urine, and jaundice (yellow coloration of the skin).

Originator

Curator's Comment: Naphthalene's chemical formula was determined by Michael Faraday in 1826. http://orchid-naphthalene.blogspot.ru/2008/09/naphthalene.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
EQUIOPATHICS WRM CLEAR

Approved Use

Indicated for the treatment of worm infestations
Palliative
ALLERGIES

Approved Use

Uses for relief of allergy symptoms affecting the mucous membranes and skin
Palliative
NAPHTHALINUM

Approved Use

Naphtalinum helps in coryza and hay fever.
PubMed

PubMed

TitleDatePubMed
Hydrocarbon deposition and soil microflora as affected by highway traffic.
2001
Characterization of the protective effects of melatonin and related indoles against alpha-naphthylisothiocyanate-induced liver injury in rats.
2001
Synthesis and pharmacology of site specific cocaine abuse treatment agents: a new synthetic methodology for methylphenidate analogs based on the Blaise reaction.
2001 Apr
Occurrence and potential adverse effects of semivolatile organic compounds in streambed sediment, United States, 1992-1995.
2001 Apr
A polyrotaxane series containing alpha-cyclodextrin and naphthalene-modified alpha-cyclodextrin as a light-harvesting antenna system.
2001 Apr 1
Development of new urea-functionalized silica stationary phases. Characterization and chromatographic performance.
2001 Apr 13
Complete prediction of the 1H NMR spectrum of organic molecules by DFT calculations of chemical shifts and spin-spin coupling constants.
2001 Apr 17
Solid-state structures of group 1 and group 2 metal 1,5-naphthalenedisulfonates: systematic investigation of lamellar three-dimensional networks constructed by metal arenedisulfonate.
2001 Aug
Efficient polycyclic aromatic hydrocarbons dihydroxylation in direct micellar systems.
2001 Aug 5
DDT, PAH and PCB in sediments from the intertidal zone of the Bohai Sea and the Yellow Sea.
2001 Feb
The effect of different oil spill remediation techniques on petroleum hydrocarbon elimination in Australian bass (Macquaria novemaculeata).
2001 Feb
Preliminary characterisation of esterase and platelet-activating factor (PAF)-acetylhydrolase activities from cat flea (Ctenocephalides felis) salivary glands.
2001 Feb
Metabolic capabilities of CYP2F2 with various pulmonary toxicants and its relative abundance in mouse lung subcompartments.
2001 Feb
Observations on the preferential biodegradation of selected components of polyaromatic hydrocarbon mixtures.
2001 Feb
Crystal structure of the 100 kDa arsenite oxidase from Alcaligenes faecalis in two crystal forms at 1.64 A and 2.03 A.
2001 Feb 7
[The toxicity variation of organic extracts in drinking water treatment processes].
2001 Jan
Absolute configuration of N-[(-)-2-(7-methoxy-1,2,3,3-tetrahydro-1-naphthyl)ethyl]cyclopropylcarboxamide, a highly potent and selective melatonin analogue.
2001 Jan
The physical basis of nucleic acid base stacking in water.
2001 Jan
Biochemical activities of trimetoquinol analogs at human beta(1)- and beta(3)-adrenergic receptors.
2001 Jan
Application of a mechanistic desorption-biodegradation model to describe the behavior of polycyclic aromatic hydrocarbons in peat soil aggregates.
2001 Jan
Structural and conformational properties of (Z)-beta-(1-naphthyl)- dehydroalanine residue.
2001 Jan
Single turnover chemistry and regulation of O2 activation by the oxygenase component of naphthalene 1,2-dioxygenase.
2001 Jan 19
Structural basis for enantiomer binding and separation of a common beta-blocker: crystal structure of cellobiohydrolase Cel7A with bound (S)-propranolol at 1.9 A resolution.
2001 Jan 5
[Bacteria--degraders of polycyclic aromatic hydrocarbons, isolated from soil and bottom sediments in salt-mining areas].
2001 Jan-Feb
Synthesis and in vitro antifungal activity of 1-amino-3,4-dialkylnaphthalene-2-carbonitriles and their analogues.
2001 Jul
Biodegradation of non-desorbable naphthalene in soils.
2001 Jul 1
Highly potent growth hormone secretagogues: hybrids of NN703 and ipamorelin.
2001 Jul 23
Active site characteristics of CYP4B1 probed with aromatic ligands.
2001 Jul 24
Synthesis of potential aldose reductase inhibitors based on minimal pharmacophore requirements.
2001 Jun
Clara cell secretory protein-expressing cells of the airway neuroepithelial body microenvironment include a label-retaining subset and are critical for epithelial renewal after progenitor cell depletion.
2001 Jun
Inhaled naphthalene causes dose dependent Clara cell cytotoxicity in mice but not in rats.
2001 Jun 1
A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes.
2001 Jun 15
2-Amino-6-arylsulfonylbenzonitriles as non-nucleoside reverse transcriptase inhibitors of HIV-1.
2001 Jun 7
Characterization of volatile organic compounds in smoke at experimental fires.
2001 Jun 8
Prior exposure to aged and diluted sidestream cigarette smoke impairs bronchiolar injury and repair.
2001 Mar
Influence of dispersants on the bioavailability and trophic transfer of petroleum hydrocarbons to larval topsmelt (Atherinops affinis).
2001 Mar
The use of a solid adsorber resin for enrichment of bacteria with toxic substrates and to identify metabolites: degradation of naphthalene, O-, and m-xylene by sulfate-reducing bacteria.
2001 Mar 1
Laboratory spectra of cold gas phase polycyclic aromatic hydrocarbon cations, and their possible relation to the diffuse interstellar bands.
2001 Mar 15
The pi complexation of alkali and alkaline earth ions by the use of meso-octaalkylporphyrinogen and aromatic hydrocarbons.
2001 Mar 16
Solvent sublation for waste minimization in a process water stream - a pilot-scale study.
2001 Mar 19
Percutaneous absorption and skin irritation of JP-8 (jet fuel).
2001 Mar 21
Synthesis, aggregation, and binding behavior of synthetic amphiphilic receptors.
2001 Mar 9
In vitro studies of the penetration of adhesive resins into artificial caries-like lesions.
2001 Mar-Apr
Mass/heat transfer in dimpled two-pass coolant passages with rotation.
2001 May
Determination of photophysical rate constants for the non-protected fluid room temperature phosphorescence of several naphthalene derivatives.
2001 May
Efficiency of naphthalene and salicylate degradation by a recombinant Pseudomonas putida mutant strain defective in glucose metabolism.
2001 May
High-rate 3-methylcatechol production in Pseudomonas putida strains by means of a novel expression system.
2001 May
Ambient air quality at the site of a former manufactured gas plant.
2001 May
Effects of occupation, lifestyle and genetic polymorphisms of CYP1A1, CYP2E1, GSTM1 and GSTT1 on urinary 1-hydroxypyrene and 2-naphthol concentrations.
2001 May
Determination of trace levels of manganese in various biological and environmental samples by atomic absorption spectrometry after solid-liquid extraction and preconcentration with the ion pair formed by the nitroso-S anion and the tetradecyldimethylbenzylammonium cation.
2001 May-Jun
Patents

Sample Use Guides

Take 4 or 6 Pellets by mouth, three times daily
Route of Administration: Oral
At the 0.10, 0.1 and 0.5 of LD(50) dose (316 mg/kg), the Naphthalene induced increases of 1.8- to 3. 9-fold in brain and liver tissue DNA fragmentation.
Substance Class Chemical
Created
by admin
on Fri Dec 16 21:43:42 UTC 2022
Edited
by admin
on Fri Dec 16 21:43:42 UTC 2022
Record UNII
2166IN72UN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAPHTHALENE
HSDB   ISO   MART.   MI   USP-RS   WHO-DD  
Systematic Name English
DEZODORATOR
Common Name English
NSC-37565
Code English
WHITE TAR
Common Name English
NAPHTHALENE [MI]
Common Name English
Naphthalene [WHO-DD]
Common Name English
NAFTALEN
Common Name English
NAPHTHALINUM
HPUS  
Common Name English
ALBOCARBON
Common Name English
NAPHTHALENE [ISO]
Common Name English
NAPHTHALINUM [HPUS]
Common Name English
NAPHTHALENE [USP-RS]
Common Name English
NAPHTHALENE [MART.]
Common Name English
NAPHTHALENE [HSDB]
Common Name English
NAPHTHALENE [IARC]
Common Name English
TAR CAMPHOR
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C45188
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
EPA PESTICIDE CODE 55801
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
Code System Code Type Description
DAILYMED
2166IN72UN
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
EPA CompTox
DTXSID8020913
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
FDA UNII
2166IN72UN
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
EVMPD
SUB128902
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
NCI_THESAURUS
C29839
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
HSDB
184
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
MERCK INDEX
M7725
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY Merck Index
NSC
37565
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
PUBCHEM
931
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
CHEBI
16482
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
RXCUI
1311149
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY RxNorm
RS_ITEM_NUM
1457083
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
CAS
91-20-3
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
WIKIPEDIA
NAPHTHALENE
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
ECHA (EC/EINECS)
202-049-5
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
MESH
C031721
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
ALANWOOD
naphthalene
Created by admin on Fri Dec 16 21:43:43 UTC 2022 , Edited by admin on Fri Dec 16 21:43:43 UTC 2022
PRIMARY
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