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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2008-10-02 13:30:03 UTC
Update Date2022-09-22 18:34:19 UTC
HMDB IDHMDB0010715
Secondary Accession Numbers
  • HMDB10715
Metabolite Identification
Common Name2-Phenylacetamide
Description2-Phenylacetamide, also known as alpha-toluamide or benzeneacetamide, belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids. Pure crystals are plate shaped and colorless to white. 2-Phenylacetamide is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Phenylacetamide exists in all living organisms, ranging from bacteria to humans. But its (apparent) unacceptable toxic effects, the most alarming being cyanosis due to methemoglobinemia and ultimately liver and kidney damage, prompted the search for supposedly less toxic aniline derivatives such as phenacetin. Acetanilide is slightly soluble in water, and stable under most conditions. Acetanilide can be produced by reacting acetic anhydride with aniline:C6H5NH2 + (CH3CO)2O → C6H5NHCOCH3 + CH3COOHThe preparation used to be a traditional experiment in introductory organic chemistry lab classes, but it has now been widely replaced by the preparation of either paracetamol or aspirin, both of which teach the same practical techniques (especially recrystallization of the product) but which avoid the use of aniline, a suspected carcinogen. It is also a precursor in the synthesis of penicillin and other pharmaceuticals. Acetanilide is no longer used as a drug in its own right, although the success of its metabolite – paracetamol (acetaminophen) – is well known (although it is itself toxic in excessive amounts). After several conflicting results over the ensuing fifty years, it was established in 1948 that acetanilide was mostly metabolized to paracetamol (acetaminophen) in the human body, and that it was this metabolite that was responsible for the analgesic and antipyretic properties. In the 19th century acetanilide was one of a large number of compounds used as experimental photographic developers. Acetanilide is used as an inhibitor of hydrogen peroxide decomposition and is used to stabilize cellulose ester varnishes. Acetanilide is an odourless solid chemical of leaf or flake-like appearance. It has also found uses in the intermediation in rubber accelerator synthesis, dyes and dye intermediate synthesis, and camphor synthesis.
Structure
Data?1582752865
Synonyms
ValueSource
alpha-PhenylacetamideKegg
a-PhenylacetamideGenerator
Α-phenylacetamideGenerator
alpha-ToluamideHMDB
BenzeneacetamideHMDB
Phenyl-beta-acetylamineHMDB
PhenylacetamideHMDB
Phenylacetic acid amideHMDB
a-ToluamideHMDB
Α-toluamideHMDB
Phenyl-b-acetylamineHMDB
Phenyl-β-acetylamineHMDB
Phenylacetate amideHMDB
(alpha-)2-PhenylacetamideHMDB
2-Phenyl-acetamideHMDB
alpha-Toluimidic acidHMDB
beta-Phenyl-acetylamineHMDB
Chemical FormulaC8H9NO
Average Molecular Weight135.1632
Monoisotopic Molecular Weight135.068413915
IUPAC Name2-phenylacetamide
Traditional Namephenylacetamide
CAS Registry Number103-81-1
SMILES
NC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)
InChI KeyLSBDFXRDZJMBSC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylacetamides. These are amide derivatives of phenylacetic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetamides
Direct ParentPhenylacetamides
Alternative Parents
Substituents
  • Phenylacetamide
  • Primary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.84 g/LALOGPS
logP0.64ALOGPS
logP0.8ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)16.5ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.19 m³·mol⁻¹ChemAxon
Polarizability14.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.59831661259
DarkChem[M-H]-124.06531661259
DeepCCS[M+H]+127.95830932474
DeepCCS[M-H]-124.62730932474
DeepCCS[M-2H]-161.74330932474
DeepCCS[M+Na]+137.0630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-PhenylacetamideNC(=O)CC1=CC=CC=C12593.1Standard polar33892256
2-PhenylacetamideNC(=O)CC1=CC=CC=C11334.4Standard non polar33892256
2-PhenylacetamideNC(=O)CC1=CC=CC=C11420.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Phenylacetamide,1TMS,isomer #1C[Si](C)(C)NC(=O)CC1=CC=CC=C11447.5Semi standard non polar33892256
2-Phenylacetamide,1TMS,isomer #1C[Si](C)(C)NC(=O)CC1=CC=CC=C11425.7Standard non polar33892256
2-Phenylacetamide,1TMS,isomer #1C[Si](C)(C)NC(=O)CC1=CC=CC=C11820.2Standard polar33892256
2-Phenylacetamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C1558.3Semi standard non polar33892256
2-Phenylacetamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C1597.7Standard non polar33892256
2-Phenylacetamide,2TMS,isomer #1C[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C1791.5Standard polar33892256
2-Phenylacetamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC=C11666.9Semi standard non polar33892256
2-Phenylacetamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC=C11643.9Standard non polar33892256
2-Phenylacetamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)CC1=CC=CC=C11948.7Standard polar33892256
2-Phenylacetamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C1987.2Semi standard non polar33892256
2-Phenylacetamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2023.6Standard non polar33892256
2-Phenylacetamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C2002.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Phenylacetamide GC-MS (2 TMS)splash10-000l-6900000000-3cbbf18204f4b2de07052014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Phenylacetamide GC-MS (1 TMS)splash10-0006-9200000000-55ad84b73efd28e150622014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Phenylacetamide GC-MS (Non-derivatized)splash10-000l-6900000000-3cbbf18204f4b2de07052017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Phenylacetamide GC-MS (Non-derivatized)splash10-0006-9200000000-55ad84b73efd28e150622017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Phenylacetamide GC-EI-TOF (Non-derivatized)splash10-0006-9200000000-89b6db1a0325e673edcb2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylacetamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-e6ef1b80ee1be92d26742017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Phenylacetamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 10V, Positive-QTOFsplash10-000f-9500000000-84ba2fa898e7e65828902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 20V, Positive-QTOFsplash10-0006-9000000000-9623a0382fbdaae6b45a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 40V, Positive-QTOFsplash10-014l-9000000000-e6bac2202565584bd5d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 35V, Positive-QTOFsplash10-0006-9000000000-0add31dc7c665b1ac05b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 10V, Positive-QTOFsplash10-0006-9200000000-e0d7e84c18f35c7ee17f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 40V, Positive-QTOFsplash10-014l-9000000000-ec10ab7c6914fd6771712021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 20V, Positive-QTOFsplash10-0006-9000000000-9096a510031f5668f0192021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 20V, Positive-QTOFsplash10-0006-9000000000-b99eb9c53f42664ae03a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 40V, Positive-QTOFsplash10-014l-9000000000-5c058521754d64b8aa682021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Phenylacetamide 10V, Positive-QTOFsplash10-0006-9200000000-6116ea4f3fc2b22bd23c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 10V, Positive-QTOFsplash10-014r-0900000000-d67563d26bb5919558162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 20V, Positive-QTOFsplash10-014l-4900000000-f91271d86bab54b239cd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 40V, Positive-QTOFsplash10-0006-9100000000-7d68220f572a4f08200b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 10V, Negative-QTOFsplash10-001i-1900000000-347d8682aa8799f5d2b42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 20V, Negative-QTOFsplash10-000x-6900000000-970db40cc13f9cc5cb642017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 40V, Negative-QTOFsplash10-0006-9100000000-0ad378c15c5c541b57492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 10V, Positive-QTOFsplash10-00kf-9800000000-223258c143c5a529a9b82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 20V, Positive-QTOFsplash10-0006-9100000000-bd85826f99fe4b8cba652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 40V, Positive-QTOFsplash10-0006-9000000000-a8f8b40d67bb9135d2b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 10V, Negative-QTOFsplash10-0006-9100000000-8e773ec020e3707879842021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 20V, Negative-QTOFsplash10-0006-9000000000-f5a600a275c36ba023312021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Phenylacetamide 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027865
KNApSAcK IDNot Available
Chemspider ID7397
KEGG Compound IDC02505
BioCyc IDCPD-238
BiGG IDNot Available
Wikipedia LinkAcetanilide
METLIN IDNot Available
PubChem Compound7680
PDB IDNot Available
ChEBI ID16562
Food Biomarker OntologyNot Available
VMH IDM00673
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
May contribute to airway host defense against infection.
Gene Name:
LPO
Uniprot ID:
P22079
Molecular weight:
70983.6
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
Reactions
L-Phenylalanine + Oxygen → 2-Phenylacetamide + Carbon dioxidedetails
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
General function:
Involved in peroxidase activity
Specific function:
Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis.
Gene Name:
EPX
Uniprot ID:
P11678
Molecular weight:
81039.5