Cannabis Compound Database: Showing Compound Card for Naphthalene (CDB005826)

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Record Information

Version

1.0

Created at

2020-04-27 17:00:25 UTC

Updated at

2021-01-04 18:49:23 UTC

CannabisDB ID

CDB005826

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Naphthalene

Description

Naphthalene, also known as white tar, camphor tar or albocarbon, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. Naphthalene exists as a white solid that evaporates easily. It has a characteristic mothball odor that is detectable at concentrations as low as 0.08 ppm by mass (PMID: 6376602 ). It is essentially insoluble in water. Naphthalene is the most abundant single component of coal tar so most of it is now industrially derived from coal tar. Naphthalene is also called white tar, and tar camphor, and was once the primary ingredient in mothballs, though its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. The single largest use of naphthalene is the industrial production of phthalic anhydride, although more phthalic anhydride is made from o-xylene. Many azo dyes are produced from naphthalene, and so is the insecticide 1-naphthyl-N-methylcarbamate (carbaryl). Burning tobacco or wood produces naphthalene. Naphthalene is also found in cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ). Naphthalene occurs naturally in many organisms and is found in trace amounts in magnolias (flowers) and some species of deer, as well as the Formosan subterranean termite. Naphthalene is apparently produced by the termite as a repellant against ants, poisonous fungi and nematode worms. Naphthalene is also found in small amounts in different foods, such as beans (0.003 mg/kg), beer (0.02 mg/kg), bilberries (0.005 mg/kg), cheese (0.035 mg/kg), chicken, cloves, cocoa (0.05 mg/kg), corn, fish, grapefruit juice, kiwi fruit, mangos, milk, peanuts, papayas, peas, peaches, plums, rice, shrimp, soybeans, black walnuts, corn, and tea. This could make naphthalene a potential biomarker for the consumption of these foods. Naphthalene is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Inhalation of naphthalene vapor has been associated with headaches, nausea, vomiting and dizziness. Naphthalene is one of over 100 known polycyclic aromatic hydrocarbons (PAHs). The ability of PAH's to bind to blood proteins such as albumin allows them to be transported throughout the body. PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. 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. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. 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. 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.

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 Weight

128.17

Monoisotopic Molecular Weight

128.0626

IUPAC Name

naphthalene

Traditional Name

naphthalene

CAS Registry Number

91-20-3

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 )

Ontology

Physiological effect

Health effect:

Health condition:

Blood and lymphatic system disorders:

Anemia

Psychiatric disorders:

Confusion

Gastrointestinal disorders:

General disorders and administration site conditions:

Fatigue

Observation:

Jaundice

Disposition

Route of exposure:

Parenteral:

Inhalation

Enteral:

Ingestion

Source:

Environmental:

Tobacco smoke

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Biofluid and excreta:

Role

Indirect biological role:

Carcinogen

Environmental role:

Industrial application:

Food and nutrition

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	80.3 °C	Not Available
Boiling Point	217.97 °C at 760 mmHg	Wikipedia
Water Solubility	0.031 mg/mL at 25 °C	Not Available
logP	3.30	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004i-2900000000-1f03568d4331683921b4	2014-09-20	View Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-28274068093bf0319e30	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-10810744223497787156	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-0900000000-f640b15d5ebd285008e9	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-2900000000-837afe39d2806871be73	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-5900000000-262e4b8e72f3d3fa0593	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-3900000000-0e32d0a2d4bb6373bea3	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-34ade0e20ab7aa4d4e7f	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-c780f74ca6838fbab7d8	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-000i-4900000000-b2e474b4d7508faeddc3	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-7900000000-43781a61560faeff786d	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-7a87251d344c519a4335	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-0900000000-0532459557fd0c543587	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-1900000000-5a22b095f0a190f1b978	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-28274068093bf0319e30	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-10810744223497787156	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-0900000000-f640b15d5ebd285008e9	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-2900000000-837afe39d2806871be73	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-5900000000-262e4b8e72f3d3fa0593	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-3900000000-0e32d0a2d4bb6373bea3	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-34ade0e20ab7aa4d4e7f	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-4900000000-c780f74ca6838fbab7d8	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-000i-4900000000-b2e474b4d7508faeddc3	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-004i-7900000000-43781a61560faeff786d	Spectrum
GC-MS	Naphthalene, non-derivatized, GC-MS Spectrum	splash10-000i-0900000000-7a87251d344c519a4335	Spectrum
Predicted GC-MS	Naphthalene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-1900000000-35bf92cf7a210b27759b	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-9058dd9b60d558e52773	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-9058dd9b60d558e52773	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-1900000000-91e4df79f1f59e0c0465	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-8575b97da509996b8151	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-8575b97da509996b8151	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-ff7fd755c09159064a33	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-71e8922109bea9aa624a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-6900000000-6558deffdb05b27a632e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-3900000000-f1f49df790d7f67edbc0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0029751

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Naphthalene

METLIN ID

Not Available

PubChem Compound

931

PDB ID

NPY

ChEBI ID

16482

References

General References

Amoore JE, Hautala E: Odor as an aid to chemical safety: odor thresholds compared with threshold limit values and volatilities for 214 industrial chemicals in air and water dilution. J Appl Toxicol. 1983 Dec;3(6):272-90. doi: 10.1002/jat.2550030603. [PubMed:6376602 ]

Showing Compound Card for Naphthalene (CDB005826)

Structure for CDB005826 (Naphthalene)