Benzamide
Chemical compound
Benzamide is an organic compound with the chemical formula of C7H7NO. It is the simplest amide derivative of benzoic acid. In powdered form, it appears as a white solid, while in crystalline form, it appears as colourless crystals. It is slightly soluble in water, and soluble in many organic solvents. It is a natural alkaloid found in the herbs of Berberis pruinosa.
01Properties
Benzamide is slightly soluble in water and soluble in polar organic solvents, including ethanol, diethyl ether, and chloroform. It has a melting point of 127-130 °C and a boiling point of 288 °C. The molecule consists of a phenyl group attached to a carboxamide group. Resonance stabilization between the carbonyl oxygen, the nitrogen atom, and the aromatic ring influences its reactivity and dipole moment.
02Applications
Pharmaceuticals
Substituted benzamides form a major class of pharmacological compounds, designated as benzamides. Derivatives of this structural pharmacophore exhibit varied biological activities:
- Antipsychotics: Sulpiride, amisulpride, and tiapride act as dopamine receptor antagonists.
- Gastroprokinetics and Antiemetics: Metoclopramide and domperidone are widely used to treat nausea and gastrointestinal disorders.
- Oncology: Benzamide derivatives, such as olaparib and entinostat, function as PARP inhibitors and histone deacetylase (HDAC) inhibitors, respectively.
Chemical Synthesis
Benzamide serves as a synthetic intermediate in industrial chemical manufacturing for dyes, agricultural chemicals, and specialty polymers.
List of Derivatives
- Analgesics
- Antidepressants
- Antiemetics/Prokinetics
- Alizapride
- Batanopride
- Bromopride
- Cinitapride
- Cisapride
- Clebopride
- Dazopride
- Itopride
- Metoclopramide
- Mosapride
- Prucalopride
- Renzapride
- Trimethobenzamide
- Veralipride
- Zacopride
- Antipsychotics
- Opioids
- Pesticides
- Others
03Toxicity and Safety
Benzamide is classified as harmful if swallowed (LD50 oral, mouse: ~1,160 mg/kg). It is listed as a Category 2 suspect germ cell mutagen based on in vitro assay data. Exposure to benzamide dust may cause mild physical irritation to the skin, eyes, and upper respiratory tract. Elevated temperatures or combustion generate toxic fumes, including nitrogen oxides and carbon monoxide.
Sources and credits
This article is adapted from the Wikipedia article “Benzamide”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Benzamide.svg by Yikrazuul, Public domain
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