Structure via PubChem · Public domain (PubChem)
2,3-epoxypropanamide
Sign in to saveAlso known as glycidamide
Glycidamide is an organic compound with the formula H2NC(O)C2H3O. It is a colorless oil. Structurally, it contains adjacent amides and epoxide functional groups. It is a bioactive, potentially toxic or even carcinogenic metabolite of acrylonitrile and acrylamide. It is a chiral molecule.
Chemical data
- Formula
- C3H5NO2
- Molecular weight
- 87.08 g/mol
- IUPAC name
- oxirane-2-carboxamide
- SMILES
- C1C(O1)C(=O)N
- InChIKey
- FMAZQSYXRGRESX-UHFFFAOYSA-N
- XLogP
- -1.2
- Polar surface area
- 55.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 87.032
Show 3 more facts
- chemical formula
- C₃H₅NO₂
- canonical SMILES
- C1C(O1)C(=O)N
- Commons category
- Glycidamide
Sources (2)
via Wikidata · CC0
~4 min read
Encyclopedic overview
8 sectionsContents
- Structure and reactivity
- Formation
- Pathology
- Reactions
- Mechanism of action
- Metabolism
- Animal studies
- References
Glycidamide is an organic compound with the formula H2NC(O)C2H3O. It is a colorless oil. Structurally, it contains adjacent amides and epoxide functional groups. It is a bioactive, potentially toxic or even carcinogenic metabolite of acrylonitrile and acrylamide. It is a chiral molecule.
== Structure and reactivity == Glycidamide is a reactive epoxide metabolite from acrylamide and can react with nucleophiles. This results in covalent binding of the electrophile.
Excerpted from Wikipedia’s “2,3-epoxypropanamide” article, available under the CC BY-SA 4.0 licence.