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Record Information
Version1.0
Creation Date2014-08-29 05:53:06 UTC
Update Date2016-11-09 01:09:04 UTC
Accession NumberCHEM003169
Identification
Common NameAcetamide
ClassSmall Molecule
DescriptionAcetamide is found in red beetroot. Acetamide (or acetic acid amide or ethanamide), CH3CONH2, the amide of acetic acid, is a white crystalline solid in pure form. It is produced by dehydrating ammonium acetate. Acetamide has been shown to exhibit anti-microbial, anti-inflammatory, anti-arthritic and antibiotic functions. Acetamide belongs to the family of Primary Carboxylic Acid Amides. These are compounds comprising primary carboxylic acid amide functional group, with the general structure RC(=O)NH2. (1, 2, 2, 3).
Contaminant Sources
  • Clean Air Act Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HPV EPA Chemicals
  • IARC Carcinogens Group 2B
  • IARC Carcinogens Group 3
  • STOFF IDENT Compounds
  • T3DB toxins
  • Tobacco Smoke Compounds
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Cigarette Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Pollutant
Chemical Structure
Thumb
Synonyms
ValueSource
AcetamidChEBI
Acetic acid amideChEBI
AzetamidChEBI
CH3CONH2ChEBI
EssigsaeureamidChEBI
EthanamidChEBI
EthanamideChEBI
MethanecarboxamideChEBI
Acetate amideGenerator
Acetimidic acidHMDB
ACMHMDB
Amid kyseliny octoveHMDB
Acetamide, monosodium saltHMDB
Chemical FormulaC2H5NO
Average Molecular Mass59.067 g/mol
Monoisotopic Mass59.037 g/mol
CAS Registry Number60-35-5
IUPAC Nameacetamide
Traditional Nameacetamide
SMILESCC(N)=O
InChI IdentifierInChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
InChI KeyDLFVBJFMPXGRIB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as carboximidic acids. These are organic acids with the general formula RC(=N)-OH (R=H, organic group).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboximidic acids and derivatives
Sub ClassCarboximidic acids
Direct ParentCarboximidic acids
Alternative Parents
Substituents
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point82 - 83°C
Boiling Point223°C (433.4°F)
Solubility2250 mg/mL at 25°C
Predicted Properties
PropertyValueSource
Water Solubility369 g/LALOGPS
logP-1.1ALOGPS
logP-1ChemAxon
logS0.8ALOGPS
pKa (Strongest Acidic)16.75ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity14.47 m³·mol⁻¹ChemAxon
Polarizability5.76 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-052f-9000000000-44ec47d45cbb6740fd6eView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9000000000-94d49b439405d0f3ad41View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0006-9000000000-94d49b439405d0f3ad41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-0a4i-9000000000-62a9b7d69257dd565e22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0a4i-9000000000-eca97902d04e534ac2d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-0a4i-9000000000-51b4caaf1d8caa1dcd66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-0a4i-9000000000-41fb86e31e458684dcc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 11V, positivesplash10-0a4i-9000000000-377e3699217c3ddf653eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-0a4l-9000000000-9ff14ca7216ed562a12bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 13V, positivesplash10-0a4l-9000000000-c5d1fbf0f4ac79ba8500View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 14V, positivesplash10-052f-9000000000-6404591bd64c77b77610View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 15V, positivesplash10-052f-9000000000-cb5bcad9d2d9b6b736f2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 16V, positivesplash10-052f-9000000000-11dd3535e54d6ff8ef85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 17V, positivesplash10-052f-9000000000-c49a0918dbfba17724c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 18V, positivesplash10-052f-9000000000-14175a412c1916e3d851View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 19V, positivesplash10-052f-9000000000-215f69c60943a78528a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-a6a33bf7f6d8f960c8bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-3fadaee55485aba6adcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c8d15248967cca08c9c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-505a068d8b00d3030e68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-0164236da39cd57f6f08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c6fa97895f0c45a9186bView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-245f2dcb7e62391b1c0aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (5)
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02736
HMDB IDHMDB0031645
FooDB IDFDB008298
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcetamide
Chemspider ID173
ChEBI ID27856
PubChem Compound ID178
Kegg Compound IDC06244
YMDB IDYMDB01563
ECMDB IDNot Available
References
Synthesis Reference

Youichi Shiokawa, Kazuo Okumura, Kazuhiko Take, Kazunori Tsubaki, “Novel substituted-acetamide compound and a process for the preparation thereof.” U.S. Patent US5066680, issued February, 1963.

MSDSLink
General References
1. Yalcin I, Kaymakcioglu BK, Oren I, Sener E, Temiz O, Akin A, Altanlar N: Synthesis and microbiological activity of some novel N-(2-hydroxyl-5-substitutedphenyl)benzacetamides, phenoxyacetamides and thiophenoxyacetamides as the possible metabolites of antimicrobial active benzoxazoles. Farmaco. 1997 Nov;52(11):685-9.
2. Jawed H, Shah SU, Jamall S, Simjee SU: N-(2-hydroxy phenyl) acetamide inhibits inflammation-related cytokines and ROS in adjuvant-induced arthritic (AIA) rats. Int Immunopharmacol. 2010 Aug;10(8):900-5. doi: 10.1016/j.intimp.2010.04.028. Epub 2010 May 7.
3. Muri EM, Williamson JS: Anti-Helicobacter pylori agents. An update. Mini Rev Med Chem. 2004 Feb;4(2):201-6.
4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.