Record Information
Version1.0
Creation date2011-09-21 00:15:08 UTC
Update date2018-05-28 18:32:56 UTC
Primary IDFDB022512
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameN-Acetylarylamine
DescriptionAcetanilide has analgesic and fever-reducing properties; it is in the same class of drugs as acetaminophen (paracetamol). Under the name acetanilid it formerly figured in the formula of a number of patent medicines and over the counter drugs. In 1948, Julius Axelrod and Bernard Brodie discovered that acetanilide is much more toxic in these applications than other drugs, causing methemoglobinemia and ultimately doing damage to the liver and kidneys. As such, acetanilide has largely been replaced by less toxic drugs, in particular acetaminophen, which is a metabolite of acetanilide and whose use Axelrod and Brodie suggested in the same study. Acetanilide is an odourless solid chemical of leaf or flake-like appearance. It is also known as N-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name antifebrin. Compounds based on N-phenylacetamide, that are similar in structure to 2-phenylacetamides. They are precursors of many other compounds. They were formerly used as analgesics and antipyretics, but often caused lethal methemoglobinemia. In the 19th century it was one of a large number of compounds used as experimental photographic developers. [HMDB]
CAS Number55576-55-1
Structure
Thumb
Synonyms
SynonymSource
AcetamidobenzeneChEBI
AcetanilChEBI
AcetanilidChEBI
AcetanilideChEBI
Acetic acid anilideChEBI
N-AcetylaminobenzeneChEBI
N-PhenylacetamideKegg
Acetate anilideGenerator
AntifebrinHMDB
N-AcetylarylamineChEBI
Predicted Properties
PropertyValueSource
Water Solubility4.03 g/LALOGPS
logP1.05ALOGPS
logP1.21ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.92 m³·mol⁻¹ChemAxon
Polarizability14.52 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H9NO
IUPAC nameN-phenylacetamide
InChI IdentifierInChI=1S/C8H9NO/c1-7(10)9-8-5-3-2-4-6-8/h2-6H,1H3,(H,9,10)
InChI KeyFZERHIULMFGESH-UHFFFAOYSA-N
Isomeric SMILESCC(=O)NC1=CC=CC=C1
Average Molecular Weight135.1632
Monoisotopic Molecular Weight135.068413915
Classification
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSN-Acetylarylamine, non-derivatized, GC-MS Spectrumsplash10-000f-9000000000-62d570000b48b0837073Spectrum
GC-MSN-Acetylarylamine, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-4122036cecde322748eaSpectrum
GC-MSN-Acetylarylamine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-5b4e4f73d383d9139de8Spectrum
GC-MSN-Acetylarylamine, non-derivatized, GC-MS Spectrumsplash10-00dr-4900000000-2293bbd44d7f9fc8077cSpectrum
GC-MSN-Acetylarylamine, non-derivatized, GC-MS Spectrumsplash10-000f-9000000000-62d570000b48b0837073Spectrum
GC-MSN-Acetylarylamine, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-4122036cecde322748eaSpectrum
GC-MSN-Acetylarylamine, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-5b4e4f73d383d9139de8Spectrum
GC-MSN-Acetylarylamine, non-derivatized, GC-MS Spectrumsplash10-00dr-4900000000-2293bbd44d7f9fc8077cSpectrum
Predicted GC-MSN-Acetylarylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-2bd7881947c0c62f2a31Spectrum
Predicted GC-MSN-Acetylarylamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0900000000-7eb05e193f729f0e27112017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000x-9700000000-e7d678f13a1e17c9ed992017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-1d77cc60e4a023d4dd222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-8877ad97a3992f9131132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-71ff77e29eb7281376052017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014r-4900000000-7f8d10f07700a193e6222017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014u-9300000000-f975b8216fe43fc1d9cc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9200000000-12e9d1610beecb011c9d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004l-9200000000-2d487e012ca3b59d0a9b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004l-9000000000-e50ad2b0e89696e088512017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0006-9000000000-46f47c26afc8877cc2f12021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-5900000000-61578dc3c9789feb5f8a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-299ec76356db162d42592016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-f918e8f5428211fb9a252016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900000000-9def162dfa4b1400554c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9500000000-137a2164ab31a33087922016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-63a8773b99832a19d5e22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9400000000-753f541f128c751917c72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-5df9abaffe7f5bdbe5d72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e621b748b2a107ee39e82021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-4900000000-b549e531b7dd15d51b672021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-60ecfd1f5d15dfbcfb812021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9000000000-df32423a180287f625672021-09-25View Spectrum
NMRNot Available
ChemSpider ID880
ChEMBL IDCHEMBL269644
KEGG Compound IDC07565
Pubchem Compound ID904
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01250
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Arylamine N-acetyltransferase 1NAT1P18440
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference