Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-04-29 21:57:25 UTC
Update Date2024-10-17 03:35:50 UTC
Metabolite IDMMDBc0048336
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
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
Molecular FormulaC8H9NO
Average Mass135.1632
Monoisotopic Mass135.068413915
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