1-Naphthol (CHEM002928)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2014-08-29 04:48:07 UTC
Update Date2026-04-17 19:33:36 UTC
Accession NumberCHEM002928
Identification
Common Name1-Naphthol
ClassSmall Molecule
Description1-naphthol (1N) is a metabolite of carbaryl and naphthalene that is an intermediate in Metabolism of xenobiotics by cytochrome P450. It is generated by spontaneous reaction from (1R,2S)-Naphthalene epoxide then is it converted to 1,4-Dihydroxynaphthalene. Although 1-Naphthol is not persistent in the body, a single urine sample may adequately predict exposure over several months to chlorpyrifos, which is a broad-spectrum organophosphate insecticide. In adult men, TCPY and 1N were associated with reduced testosterone levels (1, 2).
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • My Exposome Chemicals
  • Suspected Compounds
  • Suspected Compounds - Waste Water
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Household Toxin
  • Insecticide
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pesticide
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-HydroxynaphthaleneChEBI
1-NaphthalenolChEBI
alpha-HydroxynaphthaleneChEBI
alpha-NaphtholChEBI
a-HydroxynaphthaleneGenerator
Α-hydroxynaphthaleneGenerator
a-NaphtholGenerator
Α-naphtholGenerator
1-Naphthol, 1-(14)C-labeledMeSH
1-Naphthol, 2-(13)C-labeledMeSH
1-Naphthol, ion(1+)MeSH
1-Naphthol, lithium saltMeSH
1-Naphthol, potassium saltMeSH
1-Naphthol, sodium saltMeSH
1-Naphthyl alcoholHMDB
alpha-Naphthyl alcoholHMDB
BASF ursol ernHMDB
Durafur developer DHMDB
Fouramine ernHMDB
Fourrine 99HMDB
Fourrine ernHMDB
furro ERHMDB
nako TRBHMDB
Naphthol-1HMDB
Naphthyl-1-olHMDB
Tertral ernHMDB
Ursol ernHMDB
Zoba ernHMDB
Chemical FormulaC10H8O
Average Molecular Mass144.170 g/mol
Monoisotopic Mass144.058 g/mol
CAS Registry Number90-15-3
IUPAC Namenaphthalen-1-ol
Traditional Namenaphthol
SMILESOC1=C2C=CC=CC2=CC=C1
InChI IdentifierInChI=1S/C10H8O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-7,11H
InChI KeyKJCVRFUGPWSIIH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNaphthols and derivatives
Direct ParentNaphthols and derivatives
Alternative Parents
Substituents
  • 1-naphthol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.95 g/LALOGPS
logP2.79ALOGPS
logP2.66ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)9.6ChemAxon
pKa (Strongest Basic)-5.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.49 m³·mol⁻¹ChemAxon
Polarizability15.45 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-3900000000-61210a72d0e1913d7c72Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014l-3900000000-61210a72d0e1913d7c72Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-0900000000-c0995f3a682409c43837Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g4i-9850000000-192f1a8f4045c6c2e6a6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , negativesplash10-0006-0900000000-4e151ced4980c51dbed0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-ITFT , positivesplash10-014i-0900000000-8fc12807dac2f94e7abaSpectrum
LC-MS/MSLC-MS/MS Spectrum - APCI-ITFT , positivesplash10-014i-0900000000-c536d76de8d3df4d5774Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0006-0900000000-95369892ad06085feeaaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0006-0900000000-4359d09beb852a6b4d8dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-0002-0900000000-81d05a973c3d900077c6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-014j-0900000000-f42d4778921cb7d4089aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0900000000-5eddad361f7fcd8098bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0002-0900000000-5d003cf06a82f555ebdaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0uxr-1900000000-6b7e7dbf4dd9988bdb69Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0udi-1900000000-8f3c86f1fed8a21368e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-0900000000-ec57dc12ddf60a2741f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-014i-0900000000-751c55e1dc2b820d2fb8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-014i-0900000000-0809d3facff6212072efSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-0gb9-1900000000-f5b727eb0fe4a390c043Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-014i-0900000000-49134c89950d7d99c9d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00kf-0900000000-b57369b32440fe60da1dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-0900000000-8fc12807dac2f94e7abaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-014i-0900000000-8a33e2a4035f1d5db4c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-17872f169fc1a3b9a589Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-7ff94ab855e29de86608Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-2900000000-54aee2dee46145420c78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-3cb1d47c2a60e27a99d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-027fc605a3ec221e62c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1900000000-9d25f4653afbb98405fdSpectrum
MSMass Spectrum (Electron Ionization)splash10-00kf-2900000000-464e7ef19c6bd0e23869Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of Toxicity1-Naphthol is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
MetabolismParaoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is a natural compound that is used as a pesticide.
Minimum Risk LevelNot Available
Health EffectsAcute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.
SymptomsSymptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.
TreatmentIf the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012138
FooDB IDFDB005841
Phenol Explorer IDNot Available
KNApSAcK IDC00052604
BiGG IDNot Available
BioCyc IDNAPHTHOL
METLIN IDNot Available
PDB ID1NP
Wikipedia Link1-Naphthol
Chemspider ID6739
ChEBI ID10319
PubChem Compound ID7005
Kegg Compound IDC11714
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16721410
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18966375
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22740618
4. Meeker JD, Ryan L, Barr DB, Hauser R: Exposure to nonpersistent insecticides and male reproductive hormones. Epidemiology. 2006 Jan;17(1):61-8.
5. Hauser R, Meeker JD, Park S, Silva MJ, Calafat AM: Temporal variability of urinary phthalate metabolite levels in men of reproductive age. Environ Health Perspect. 2004 Dec;112(17):1734-40.