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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 16:24:27 UTC
Update Date2021-10-13 04:43:33 UTC
HMDB IDHMDB0004296
Secondary Accession Numbers
  • HMDB04296
Metabolite Identification
Common NameAcrylamide
DescriptionAcrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. It is produced industrially as a precursor to polyacrylamides, which find many uses as water-soluble thickeners and flocculation agents. It is highly toxic, likely to be carcinogenic,and partly for that reason it is mainly handled as an aqueous solution. It is a chemical used in many industries around the world and more recently was found to form naturally in foods cooked at high temperatures. Acrylamide is a neurotoxicant, reproductive toxicant, and carcinogen in animal species. Only the neurotoxic effects have been observed in humans and only at high levels of exposure in occupational settings. The mechanism underlying neurotoxic effects of ACR may be basic to the other toxic effects seen in animals. This mechanism involves interference with the kinesin-related motor proteins in nerve cells or with fusion proteins in the formation of vesicles at the nerve terminus and eventual cell death. Neurotoxicity and resulting behavioral changes can affect reproductive performance of ACR-exposed laboratory animals with resulting decreased reproductive performance. Further, the kinesin motor proteins are important in sperm motility, which could alter reproduction parameters. Effects on kinesin proteins could also explain some of the genotoxic effects on ACR. These proteins form the spindle fibers in the nucleus that function in the separation of chromosomes during cell division. This could explain the clastogenic effects of the chemical noted in a number of tests for genotoxicity and assays for germ cell damage. Other mechanisms underlying ACR-induced carcinogenesis or nerve toxicity are likely related to an affinity for sulfhydryl groups on proteins. Binding of the sulfhydryl groups could inactive proteins/enzymes involved in DNA repair and other critical cell functions. Direct interaction with DNA may or may not be a major mechanism for cancer induction in animals. The DNA adducts that form do not correlate with tumor sites and ACR is mostly negative in gene mutation assays except at high doses that may not be achievable in the diet. All epidemiologic studies fail to show any increased risk of cancer from either high-level occupational exposure or the low levels found in the diet. In fact, two of the epidemiologic studies show a decrease in cancer of the large bowel. A number of risk assessment studies were performed to estimate increased cancer risk. The results of these studies are highly variable depending on the model. There is universal consensus among international food safety groups in all countries that examined the issue of ACR in the diet that not enough information is available at this time to make informed decisions on which to base any regulatory action. Too little is known about levels of this chemical in different foods and the potential risk from dietary exposure. Avoidance of foods containing ACR would result in worse health issues from an unbalanced diet or pathogens from under cooked foods. There is some consensus that low levels of ACR in the diet are not a concern for neurotoxicity or reproductive toxicity in humans, although further research is need to study the long-term, low-level cumulative effects on the nervous system. Any relationship to cancer risk from dietary exposure is hypothetical at this point and awaits more definitive studies. (PMID:17492525 ).
Structure
Data?1582752305
Synonyms
ValueSource
2-PropenamideChEBI
AkrylamidChEBI
EthylenecarboxamideChEBI
2-PropeneamideHMDB
AcrylagelHMDB
Acrylic acid amideHMDB
Acrylic amideHMDB
Aerofloc 3453HMDB
American cyanamid kpamHMDB
American cyanamid P-250HMDB
Amid kyseliny akryloveHMDB
Amide propenoateHMDB
Amide propenoic acidHMDB
Aminogen paHMDB
amresco Acryl-40HMDB
bio-Gel P 2HMDB
BioGel P-100HMDB
Cyanamer P 250HMDB
Cyanamer P 35HMDB
Cytame 5HMDB
Dow et 597HMDB
Ethylene carboxamideHMDB
Flokonit eHMDB
Flygtol GBHMDB
Gelamide 250HMDB
Himoloc SS 200HMDB
K-PamHMDB
Magnafloc R 292HMDB
Nacolyte 673HMDB
OptimumHMDB
PolyacrylamideHMDB
Polyacrylamide resinHMDB
Polyacrylamide solutionHMDB
Polyhall 27HMDB
Polyhall 402HMDB
PolystolonHMDB
PolystoronHMDB
PorisutoronHMDB
Praestol 2800HMDB
Prop-2-enamideHMDB
PropenamideHMDB
PropeneamideHMDB
PropenoateHMDB
Propenoic acidHMDB
Propenoic acid amideHMDB
Reten 420HMDB
Sanpoly a 520HMDB
Solvitose 433HMDB
Stipix adHMDB
Stokopol D 2624HMDB
Sumirez a 17HMDB
Sumirez a 27HMDB
Sumitex a 1HMDB
Superfloc 84HMDB
Superfloc 900HMDB
Sursolan P 5HMDB
Versicol W 11HMDB
Vinyl amideHMDB
Chemical FormulaC3H5NO
Average Molecular Weight71.0779
Monoisotopic Molecular Weight71.037113787
IUPAC Nameprop-2-enamide
Traditional Nameacrylamide
CAS Registry Number79-06-1
SMILES
NC(=O)C=C
InChI Identifier
InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)
InChI KeyHRPVXLWXLXDGHG-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
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point84.5 °CNot Available
Boiling Point192.60 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility390 mg/mL at 25 °CNot Available
LogP-0.67HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility120 g/LALOGPS
logP-0.65ALOGPS
logP-0.27ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)16.7ChemAxon
pKa (Strongest Basic)0.0026ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity19.11 m³·mol⁻¹ChemAxon
Polarizability6.88 ųChemAxon
Number of Rings0ChemAxon
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]+112.0831661259
DarkChem[M-H]-104.17431661259
DeepCCS[M+H]+120.67930932474
DeepCCS[M-H]-118.25930932474
DeepCCS[M-2H]-154.24930932474
DeepCCS[M+Na]+128.79430932474
AllCCS[M+H]+121.532859911
AllCCS[M+H-H2O]+116.932859911
AllCCS[M+NH4]+125.832859911
AllCCS[M+Na]+127.032859911
AllCCS[M-H]-128.632859911
AllCCS[M+Na-2H]-134.232859911
AllCCS[M+HCOO]-140.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AcrylamideNC(=O)C=C1903.9Standard polar33892256
AcrylamideNC(=O)C=C726.4Standard non polar33892256
AcrylamideNC(=O)C=C828.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Acrylamide,1TMS,isomer #1C=CC(=O)N[Si](C)(C)C961.4Semi standard non polar33892256
Acrylamide,1TMS,isomer #1C=CC(=O)N[Si](C)(C)C1055.8Standard non polar33892256
Acrylamide,1TMS,isomer #1C=CC(=O)N[Si](C)(C)C1272.8Standard polar33892256
Acrylamide,2TMS,isomer #1C=CC(=O)N([Si](C)(C)C)[Si](C)(C)C1118.2Semi standard non polar33892256
Acrylamide,2TMS,isomer #1C=CC(=O)N([Si](C)(C)C)[Si](C)(C)C1071.7Standard non polar33892256
Acrylamide,2TMS,isomer #1C=CC(=O)N([Si](C)(C)C)[Si](C)(C)C1202.4Standard polar33892256
Acrylamide,1TBDMS,isomer #1C=CC(=O)N[Si](C)(C)C(C)(C)C1205.9Semi standard non polar33892256
Acrylamide,1TBDMS,isomer #1C=CC(=O)N[Si](C)(C)C(C)(C)C1246.1Standard non polar33892256
Acrylamide,1TBDMS,isomer #1C=CC(=O)N[Si](C)(C)C(C)(C)C1432.7Standard polar33892256
Acrylamide,2TBDMS,isomer #1C=CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1561.4Semi standard non polar33892256
Acrylamide,2TBDMS,isomer #1C=CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1526.3Standard non polar33892256
Acrylamide,2TBDMS,isomer #1C=CC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C1430.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Acrylamide EI-B (Non-derivatized)splash10-05dl-9000000000-7803f8bd1c25c6f335932017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acrylamide EI-B (Non-derivatized)splash10-0fbc-9000000000-5172c72b521a27969d002017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acrylamide EI-B (Non-derivatized)splash10-05dl-9000000000-1bf9b49a192db4be57182017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acrylamide EI-B (Non-derivatized)splash10-05dl-9000000000-7803f8bd1c25c6f335932018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acrylamide EI-B (Non-derivatized)splash10-0fbc-9000000000-5172c72b521a27969d002018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Acrylamide EI-B (Non-derivatized)splash10-05dl-9000000000-1bf9b49a192db4be57182018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acrylamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00b9-9000000000-5bef29cbd40aff79956d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acrylamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Acrylamide 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 - Acrylamide Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-05fr-9000000000-7b30073e15256ba58af12012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylamide Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0udi-9000000000-26ca703d558096e73e802012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylamide Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0kfx-9000000000-da086ba0e1b4f10d534f2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylamide EI-B (Unknown) , Positive-QTOFsplash10-05dl-9000000000-2c812f3ba789fd9496622012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylamide EI-B (HITACHI RMU-7M) , Positive-QTOFsplash10-0fbc-9000000000-133d475aa82b7785e9d92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylamide EI-B (HITACHI M-60) , Positive-QTOFsplash10-05dl-9000000000-1a51b235c01925474be92012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylamide 20V, Positive-QTOFsplash10-0a4i-9000000000-9abb65794a256ec349d92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylamide 40V, Positive-QTOFsplash10-0006-9000000000-731632d5d897092e87932021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Acrylamide 10V, Positive-QTOFsplash10-0a4i-9000000000-7ae060a514404849e18b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 10V, Positive-QTOFsplash10-0ab9-9000000000-266bb2ee5e50895cafcd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 20V, Positive-QTOFsplash10-0a4i-9000000000-f050957a0d6ea8faffa92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 40V, Positive-QTOFsplash10-0a6r-9000000000-c07c1b77eefb52c831b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 10V, Negative-QTOFsplash10-00di-9000000000-aeb4a4f6e2bfac854f782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 20V, Negative-QTOFsplash10-00di-9000000000-9dbeef50bde3f71563c72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 40V, Negative-QTOFsplash10-0f6x-9000000000-a47b3ab799000bb0943f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 10V, Positive-QTOFsplash10-0a4i-9000000000-3f00472f65fff4471b252021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 20V, Positive-QTOFsplash10-0a4i-9000000000-f7af528f16b7b525e1d92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 40V, Positive-QTOFsplash10-0pbc-9000000000-a4a3d985da910e7d55bd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 10V, Negative-QTOFsplash10-00di-9000000000-824624715e96152c7f472021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 20V, Negative-QTOFsplash10-006x-9000000000-9c5330c894f80f4d61fe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Acrylamide 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008308
KNApSAcK IDC00032372
Chemspider ID6331
KEGG Compound IDC01659
BioCyc IDCPD-2204
BiGG IDNot Available
Wikipedia LinkAcrylamide
METLIN IDNot Available
PubChem Compound6579
PDB IDNot Available
ChEBI ID28619
Food Biomarker OntologyNot Available
VMH IDAA
MarkerDB IDNot Available
Good Scents IDrw1216131
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Exon JH: A review of the toxicology of acrylamide. J Toxicol Environ Health B Crit Rev. 2006 Sep-Oct;9(5):397-412. [PubMed:17492525 ]