ContaminantDB: Acrylamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (50)XML

Record Information

Version

1.0

Creation Date

2009-07-05 03:32:38 UTC

Update Date

2026-03-31 17:51:32 UTC

Accession Number

CHEM002098

Identification

Common Name

Acrylamide

Class

Small Molecule

Description

Acrylamide (ACR) 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. (6).

Contaminant Sources

Clean Air Act Chemicals
EAFUS Chemicals
ECHA Carcinogen
FooDB Chemicals
HPV EPA Chemicals
IARC Carcinogens Group 2A
OECD HPV Chemicals
STOFF IDENT Compounds
T3DB toxins
Tobacco Smoke Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Cigarette Toxin
Cosmetic Toxin
Food Toxin
Household Toxin
Industrial Precursor/Intermediate
Industrial/Workplace Toxin
Metabolite
Organic Compound
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2-Propenamide	ChEBI
Akrylamid	ChEBI
Ethylenecarboxamide	ChEBI
2-Propeneamide	HMDB
Acrylagel	HMDB
Acrylic acid amide	HMDB
Acrylic amide	HMDB
Aerofloc 3453	HMDB
American cyanamid kpam	HMDB
American cyanamid P-250	HMDB
Amid kyseliny akrylove	HMDB
Amide propenoate	HMDB
Amide propenoic acid	HMDB
Aminogen pa	HMDB
amresco Acryl-40	HMDB
bio-Gel P 2	HMDB
BioGel P-100	HMDB
Cyanamer P 250	HMDB
Cyanamer P 35	HMDB
Cytame 5	HMDB
Dow et 597	HMDB
Ethylene carboxamide	HMDB
Flokonit e	HMDB
Flygtol GB	HMDB
Gelamide 250	HMDB
Himoloc SS 200	HMDB
K-Pam	HMDB
Magnafloc R 292	HMDB
Nacolyte 673	HMDB
Optimum	HMDB
Polyacrylamide	HMDB
Polyacrylamide resin	HMDB
Polyacrylamide solution	HMDB
Polyhall 27	HMDB
Polyhall 402	HMDB
Polystolon	HMDB
Polystoron	HMDB
Porisutoron	HMDB
Praestol 2800	HMDB
Prop-2-enamide	HMDB
Propenamide	HMDB
Propeneamide	HMDB
Propenoate	HMDB
Propenoic acid	HMDB
Propenoic acid amide	HMDB
Reten 420	HMDB
Sanpoly a 520	HMDB
Solvitose 433	HMDB
Stipix ad	HMDB
Stokopol D 2624	HMDB
Sumirez a 17	HMDB
Sumirez a 27	HMDB
Sumitex a 1	HMDB
Superfloc 84	HMDB
Superfloc 900	HMDB
Sursolan P 5	HMDB
Versicol W 11	HMDB
Vinyl amide	HMDB

Chemical Formula

C₃H₅NO

Average Molecular Mass

71.078 g/mol

Monoisotopic Mass

71.037 g/mol

CAS Registry Number

1979-06-01

IUPAC Name

prop-2-enamide

Traditional Name

acrylamide

SMILES

NC(=O)C=C

InChI Identifier

InChI=1S/C3H5NO/c1-2-3(4)5/h2H,1H2,(H2,4,5)

InChI Key

HRPVXLWXLXDGHG-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboximidic acids and derivatives

Sub Class

Carboximidic acids

Direct Parent

Carboximidic acids

Alternative Parents

Substituents

Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

acrylamides (CHEBI:28619 )
a small molecule (ACRYLAMIDE )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

All Tissues

Pathways

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Maillard reaction product

Physical Properties

State

Solid

Appearance

White powder

Experimental Properties

Property	Value
Melting Point	84.5 °C
Boiling Point	125°C (257°F)
Solubility	390 mg/mL at 25 °C

Predicted Properties

Property	Value	Source
Water Solubility	120 g/L	ALOGPS
logP	-0.65	ALOGPS
logP	-0.27	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	16.7	ChemAxon
pKa (Strongest Basic)	0.0026	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	19.11 m³·mol⁻¹	ChemAxon
Polarizability	6.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05dl-9000000000-7803f8bd1c25c6f33593	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fbc-9000000000-5172c72b521a27969d00	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05dl-9000000000-1bf9b49a192db4be5718	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05dl-9000000000-7803f8bd1c25c6f33593	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0fbc-9000000000-5172c72b521a27969d00	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-05dl-9000000000-1bf9b49a192db4be5718	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00b9-9000000000-5bef29cbd40aff79956d	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-05fr-9000000000-7b30073e15256ba58af1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-9000000000-26ca703d558096e73e80	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0kfx-9000000000-da086ba0e1b4f10d534f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-05dl-9000000000-2c812f3ba789fd949662	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-0fbc-9000000000-133d475aa82b7785e9d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-05dl-9000000000-1a51b235c01925474be9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9abb65794a256ec349d9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-731632d5d897092e8793	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-7ae060a514404849e18b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-9000000000-266bb2ee5e50895cafcd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-f050957a0d6ea8faffa9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9000000000-c07c1b77eefb52c831b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-aeb4a4f6e2bfac854f78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-9dbeef50bde3f71563c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9000000000-a47b3ab799000bb0943f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9000000000-3f00472f65fff4471b25	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-f7af528f16b7b525e1d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbc-9000000000-a4a3d985da910e7d55bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9000000000-824624715e96152c7f47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-9000000000-9c5330c894f80f4d61fe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (10) ; dermal (10) ; dermal (10) ; oral (10).

Mechanism of Toxicity

Acrylamide produces a central-peripheral distal axonopathy when administered chronically. This is characterized functionally by decreases in the monosynaptic reflex and dorsal root potential and alterations in the characteristics of the dorsal root reflex. Acrylamide's neurotoxic effects may be caused by the disruption of fast axonal transport. Acrylamide is thought to bind to kinesin, which leads to impairment of the fast axonal transport system responsible for the distal delivery of macromolecules. This results in deficiencies in proteins responsible for maintaining axonal structure and function. Acrylamide may also disrupt nitric oxide signaling at nerve terminals by forming adducts with soft nucleophilic sulfhydryl groups on cysteine residues. In terms of reproductive toxicity, data suggest that acrylamide-induced male dominant lethal mutations may involve clastogenic events from binding of acrylamide and/or glycidamide to spermatid protamines or spindle fiber proteins and/or direct alkylation of DNA by glycidamide. Adverse effects on mounting, sperm motility, and intromission could also be related to distal axonopathy resulting from binding of acrylamide to motor proteins. Acrylamide's mechanism of carcinogenicity is likely mutagenic, as the metabolite glycidamide is believed to react with proteins and DNA, causing mutations that persist in viable somatic cells and resulting in tumor formation. In addition, acrylamide's affinity for binding sulfhydryl groups on proteins could inactive proteins/enzymes involved in DNA repair and other critical cell functions. (1, 11, 6)

Metabolism

Acrylamide is absorbed following oral, inhalation, and dermal exposure and is widely distributed, tending to accumulate in the red blood cells. In the proposed major metabolic pathway acrylamide reacts with glutathione to form S-beta-propionamide glutathione conjugate which is excreted in the urine as cysteine or N-acetylcysteine derivatives. The major urinary metabolite (accounting for 48% of the excreted dose) is N-acetylcysteine-S-beta-propionamide. Alternately, acrylamide may be oxidized to glycidamide by CYP2E1. Glycidamide then goes on to form similar glutathione conjugates or undergos hydrolysis, leading to the formation of 2,3-dihydroxypropionamide and 2,3-dihydroxypropionicacid. (5, 2, 11)

Toxicity Values

0.83 microg/kg/day based on reproductive effects, 1.2 microg/kg/day based on neurotoxicity and 1.5 microg/kg/day based on cancer (8)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

2A, probably carcinogenic to humans. (9)

Uses/Sources

Most acrylamide is used to synthesize polyacrylamides, which find many uses as water-soluble thickeners. Polyacrylamide was first used in a laboratory setting as polyacrylamide gel electrophoresis to separate charged molecules. Acrylamide has many other uses in molecular biology laboratories, including the use of linear polyacrylamide (LPA) as a carrier which aids in the precipitation of small amounts of DNA. Many laboratory supply companies sell LPA for this use. Some acrylamide is used in the manufacture of dyes and the manufacture of other monomers. Acrylamide also occurs in many cooked starchy foods, such as potato chips and French fries. (10)

Minimum Risk Level

<0.83 microg/kg/day based on reproductive effects, 1.2 microg/kg/day based on neurotoxicity and 1.5 microg/kg/day based on cancer (8)

Health Effects

Acrylamide is neurotoxic and causes the disassembly or rearrangement of intermediate filaments. It may also damage the male reproductive glands and is believed to be carcinogenic. (10)

Symptoms

Direct exposure to pure acrylamide by inhalation, skin absorption, or eye contact irritates the exposed mucous membranes and can also cause sweating, urinary incontinence, nausea, myalgia, speech disorders, numbness, paresthesia, and weakened legs and hands. (10)

Treatment

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0004296

FooDB ID

FDB008308

Phenol Explorer ID

Not Available

KNApSAcK ID