Benzamide - Wikipedia

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• 3 References
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Appearance move to sidebar hide From Wikipedia, the free encyclopedia Benzamide

Names
Preferred IUPAC name Benzamide[1]
Systematic IUPAC name Benzenecarboxamide
Other names Benzoic acid amidePhenyl carboxamideBenzoylamide
Identifiers
CAS Number	55-21-0 Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	385876
ChEBI	CHEBI:28179 Y
ChEMBL	ChEMBL267373 Y
ChemSpider	2241 Y
ECHA InfoCard	100.000.207
EC Number	200-227-7
KEGG	C09815 Y
PubChem CID	2331
RTECS number	CU8700000
UNII	6X80438640 Y
CompTox Dashboard (EPA)	DTXSID0021709
InChI InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9) YKey: KXDAEFPNCMNJSK-UHFFFAOYSA-N Y InChI=1/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)Key: KXDAEFPNCMNJSK-UHFFFAOYAA
SMILES O=C(N)c1ccccc1 c1ccc(cc1)C(=O)N
Properties
Chemical formula	C7H7NO
Molar mass	121.139 g·mol−1
Appearance	Off-white solid
Density	1.341 g/cm3
Melting point	127 to 130 °C (261 to 266 °F; 400 to 403 K)
Boiling point	288 °C (550 °F; 561 K)
Solubility in water	13.5 g/L (at 25°C)[2]
Acidity (pKa)	approx. 13 (in H2O)[3] 23.3 (in DMSO)[4]
Magnetic susceptibility (χ)	−72.3·10−6 cm3/mol
Pharmacology
ATC code	N05AL (WHO)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H341
Precautionary statements	P201, P202, P264, P270, P281, P301+P312, P308+P313, P330, P405, P501
NFPA 704 (fire diamond)	1 1 0
Flash point	180 °C (356 °F; 453 K)
Autoignitiontemperature	> 500 °C (932 °F; 773 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

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.[5] It is slightly soluble in water,[2] and soluble in many organic solvents.[6] It is a natural alkaloid found in the herbs of Berberis pruinosa.[6]

Chemical derivatives

[edit]

A number of substituted benzamides are commercial drugs, including:

Analgesics

• Ethenzamide
• Salicylamide

Antidepressants

• Moclobemide

Antiemetics/Prokinetics

• Alizapride
• Batanopride
• Bromopride
• Cinitapride
• Cisapride
• Clebopride
• Dazopride
• Itopride
• Metoclopramide
• Mosapride
• Prucalopride
• Renzapride
• Trimethobenzamide
• Veralipride
• Zacopride

Antipsychotics

• Azapride
• Amisulpride
• Levosulpiride
• Nemonapride
• Remoxipride
• Sulpiride
• Sultopride
• Tiapride

Opioids

• AH-7921
• Bromadoline
• U-47700
• U-77891

Others

• 3-Aminobenzamide
• Alpiropride
• Aminohippuric acid
• Chidamide
• Entinostat
• Eticlopride
• Imatinib
• Mocetinostat
• Procarbazine
• Raclopride
• Sunifiram

See also

[edit]

• ATC code N05AL Benzamides – Pharmaceutical drug classification

References

[edit]

1. ^ Favre, Henri A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. p. 841. doi:10.1039/9781849733069-FP001. ISBN 9780854041824. OCLC 1077224056. Archived from the original on 2022-10-11. Retrieved 2022-10-11.
2. ^ a b "Benzamide | 55-21-0 supplier and manufacturer". BuyersGuideChem. Archived from the original on July 29, 2017. Retrieved October 11, 2022.
3. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89 [sic]. ISBN 9781498754286. OCLC 1012162798. Archived from the original on 2022-10-11. Retrieved 2022-10-11. page cited is 5-89, not 5 to 89
4. ^ Bordwell, Frederick G.; Ji, Guo Zhen (October 1991). "Effects of structural changes on acidities and homolytic bond dissociation energies of the hydrogen-nitrogen bonds in amidines, carboxamides, and thiocarboxamides". Journal of the American Chemical Society. 113 (22): 8398–8401. doi:10.1021/ja00022a029. Archived from the original on 2020-12-11. Retrieved 2022-10-11.
5. ^ CID 2331 from PubChem
6. ^ a b "benzamide, CAS number 55-21-0". The Good Scents Company. Retrieved October 11, 2022.

External links

[edit]

• Physical characteristics
• Safety MSDS data

v t e Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Bromperidol decanoate Droperidol Haloperidol# Haloperidol decanoate Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acepromazine Acetophenazine Butaperazine Carphenazine (carfenazine)‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Fluphenazine decanoate Fluphenazine enanthate Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine BL-1020 Perphenazine decanoate Perphenazine enanthate Piperacetazine Pipotiazine Pipotiazine palmitate Pipotiazine undecylenate Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Clopenthixol decanoate Flupentixol Flupentixol decanoate Tiotixene (thiothixene) Zuclopenthixol Zuclopenthixol acetate Zuclopenthixol decanoate
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride‡ Sulpiride Sultopride Tiapride Veralipride‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Oxyprothepin decanoate Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Milsaperidone Paliperidone Paliperidone palmitate Perospirone Risperidone# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine# Olanzapine (+samidorphan) Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Monoamine-depleting agents: Oxypertine Reserpine Tetrabenazine Muscarinic agonists: Xanomeline/trospium chloride Others/unknown: Azacyclonol
#WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III

v t e Antiemetics (A04)
5-HT3 serotonin ion channel antagonists	Alosetron Azasetron Bemesetron Cilansetron Clozapine Dazopride Dolasetron Granisetron Lerisetron Mianserin Mirtazapine Olanzapine Ondansetron Palonosetron (+netupitant) Quetiapine Ramosetron Ricasetron Tropisetron Zatosetron
5-HT serotonin G-protein receptor antagonists	Clozapine Cyproheptadine Hydroxyzine Olanzapine Risperidone Ziprasidone
CB1 agonists (cannabinoids)	Dronabinol Nabilone Tetrahydrocannabinol (cannabis)
D2/D3 antagonists	Chlorpromazine Haloperidol Hydroxyzine Metoclopramide Metopimazine Prochlorperazine Thiethylperazine Trimethobenzamide
H1 antagonists (antihistamines)	Cyclizine Dimenhydrinate Diphenhydramine Hydroxyzine Meclizine Promethazine
mACh antagonists (anticholinergics)	Atropine Diphenhydramine Hydroxyzine (very mild) Hyoscyamine Scopolamine
NK1 antagonists	Aprepitant Fosaprepitant Maropitant Netupitant Rolapitant Tradipitant
Others	Amisulpride Cerium oxalate Dexamethasone Lorazepam Midazolam Propofol

v t e Drugs for functional gastrointestinal disorders (A03)
Drugs for functional bowel disorders	Antimuscarinics Tertiary amino group Camylofin Dicycloverine Difemerine Dihexyverine Mebeverine Oxyphencyclimine Piperidolate Rociverine Trimebutine Quaternary ammonium compounds Benzilone Bevonium Diphemanil Fenpiverinium Glycopyrronium Hexocyclium Isopropamide Mepenzolate Methantheline Otilonium Oxyphenonium Penthienate Pipenzolate Poldine Prifinium Propantheline Tiemonium Timepidium Tridihexethyl Phosphodiesterase inhibitors Drotaverine Moxaverine Papaverine Acting on serotonin receptors 5-HT3 antagonists Alosetron Cilansetron 5-HT4 agonists Mosapride Other Alverine Caroverine Chlorbenzoxamine Diisopromine Dimethylaminopropionylphenothiazine Fenoverine Fenpiprane Idanpramine Isometheptene Mentha piperita Phloroglucinol Pinaverium bromide Proxazole Simeticone Tiropramide Trepibutone Trimethyldiphenylpropylamine
Belladonna and derivatives (antimuscarinics)	Tertiary amines: Atropine Hyoscyamine Quaternary ammonium compounds: Scopolamine Butylscopolamine Methylscopolamine Cimetropium bromide Fentonium bromide Methylatropine
Propulsives	Primarily dopamine antagonists Alizapride Bromopride Clebopride Domperidone Metoclopramide 5-HT4 agonists Cinitapride Cisapride Acotiamide Ilebopride Mosapride

v t e Analgesics (N02A, N02B)
Opioids	Opiates/opium Codeine# +aspirin +paracetamol Morphine# (+naltrexone) Opium Laudanum Paregoric Semisynthetic Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Papaveretum Thebacon Synthetic Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl# (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone# NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tegileridine Tilidine Tramadol (+celecoxib, +paracetamol) Viminol
Paracetamol-type	Acetanilide‡ Bucetin‡ Butacetin‡ Paracetamol (acetaminophen)# +aspirin/caffeine +butalbital +codeine +hydrocodone +ibuprofen +metoclopramide +oxycodone +propyphenazone/caffeine +tramadol Parapropamol‡ Phenacetin‡ Propacetamol‡
NSAIDs	Propionates Benoxaprofen ‡ Fenoprofen Flurbiprofen Ibuprofen# (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen Oxicams Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam Acetates Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac ‡ COX-2 inhibitors Celecoxib (+tramadol) Etoricoxib Lumiracoxib ‡ Parecoxib Rofecoxib ‡ Valdecoxib ‡ Fenamates Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid Salicylates Aspirin (acetylsalicylic acid)# (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate) Pyrazolones Aminophenazone‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine) Others Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone
Cannabinoids	Cannabidiol Cannabis Nabilone Nabiximols Tetrahydrocannabinol (dronabinol)
Ion channelmodulators	Calcium blockers Alcohol (ethanol) Gabapentin Gabapentin enacarbil Leconotide Mirogabalin Pregabalin Ziconotide Sodium blockers Carbamazepine Lacosamide Local anesthetics (e.g., cocaine, lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g., amitriptyline#) Nav1.7/1.8-selective: DSP-2230§ Funapide§ PF-05089771§ Suzetrigine Potassium openers Flupirtine‡
Myorelaxants	Carisoprodol Chlorzoxazone Cyclobenzaprine Mephenoxalone Methocarbamol Orphenadrine
Others	Analgecine Analgesic adjuvant Bedinvetmab Camphor Capsaicin Clonidine Frunevetmab Izenivetmab Ketamine Menthol Methoxyflurane Phenazopyridine Proglumide Relfovetmab Rimazolium Tanezumab
#WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III

v t e Chemical classes of psychoactive drugs
Stimulants	Amphetamine-type/dopamine releasing agents: Alkylamines Cycloalkylaminopropanes Arylpiperazines Benzylpiperazines Phenylpiperazines Phenethylamines Aminorexes/phenyloxazolamines Amphetamines/α-methylphenethylamines Cathinones/β-ketoamphetamines β-Hydroxyamphetamines/cathinols Naphthylaminopropanes Phentermines Phenylisobutylamines/α-ethylphenethylamines α-Propylphenethylamines Phenylmorpholines/phenmetrazines Thiopropamines/thienylaminopropanes Cocaine-type/typical dopamine reuptake inhibitors: Phenethylamines Phenidates/benzylpiperidines Phenylethylpyrrolidines Pyrrolidinophenones Phenyltropanes/cocaine analogues Modafinil-type/atypical dopamine reuptake inhibitors: Modafinil analogues Phenylpiracetams Caffeine-type/adenosine receptor antagonists: Xanthines/methylxanthines Nicotine-type/nicotinic acetylcholine receptor agonists: Nicotine analogues
Depressants	GABAA receptor positive allosteric modulators: Alcohols/ethanol analogues Barbiturates Benzodiazepines Pyrrolobenzodiazepines Thienobenzodiazepines Thienodiazepines Thienotriazolodiazepines Triazolobenzodiazepines Carbamates Ethers Neuroactive steroids Nonbenzodiazepines β-Carbolines Cyclopyrrolones Imidazopyridines Pyrazolopyrimidines Phenols Piperidinediones Quinazolinones GABAA receptor agonists: Isoxazoles GHB receptor agonists: 1,4-Butanediols α2δ subunit-containing voltage-gated calcium channel blockers: Gabapentinoids Opioids/μ-opioid receptor agonists: Benzimidazoles Nitazenes Fentanyl analogues/phenylpiperidines Mitragyna alkaloids Morphinans/phenanthrenes Opiates/opium alkaloids Utopioids Antihistamines/H1 receptor antagonists: Benzimidazoles Diarylmethanes Ethylenediamines Tricyclics Dibenzocycloheptenes
Hallucinogens	Serotonergic psychedelics/serotonin 5-HT2A receptor agonists: Arylpiperazines Phenylpiperazines Quinolinylpiperazines Cyclized phenethylamines 3-Benzazepines Cyclized tryptamines Azepinoindoles Ibogalogs Iboga alkaloids β-Carbolines Harmala alkaloids Ergolines Lysergamides Simplified/partial lysergamides Phenethylamines (methoxyphenethylamines) 2Cs 25-NB/NBOMes 2C-Os 2C-Ts HOT-x TWEETIOs Amphetamines/α-methylphenethylamines 3Cs Dimethoxyamphetamines/DMAs DOx Alephs Ethylenedioxyamphetamines/EDxx Methylenedioxyamphetamines/MDxx Trimethoxyamphetamines/TMAs BOx FLYs/benzofurans Phenylisobutylamines/α-ethylphenethylamines 4Cs Scalines Ψ-PEAs Tryptamines α-Alkyltryptamines α-Alkyl-β-ketotryptamines 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Miscellaneous Dissociatives/NMDA receptor antagonists: Adamantanes Arylcyclohexylamines Diarylethylamines Morphinans κ-Opioid receptor agonists: Benzomorphans Salvinorins GABAA receptor agonists: Isoxazoles Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists: Diarylmethanes Tropanes Others: Cyclized tryptamines Azepinoindoles Iboga alkaloids (Phyto)cannabinoids
Entactogens	Serotonin releasing agents: Phenethylamines 2-Aminoindanes 2-Aminotetralins Amphetamines Benzofuranylaminopropanes Benzothiophenylaminopropanes Ethylenedioxyamphetamines/EDxx Indanylaminopropanes Indolylaminopropanes Methylenedioxyamphetamines/MDxx Tetralinylaminopropanes Tryptamines α-Alkyltryptamines Miscellaneous
Psychiatric drugs	Anxiolytics: Azapirones Benzodiazepines Pyrrolobenzodiazepines Thienobenzodiazepines Thienodiazepines Thienotriazolodiazepines Triazolobenzodiazepines Antidepressants: Tricyclic antidepressants Dibenzazepines Dibenzocycloheptenes Dibenzothiepins Dibenzoxazepines Dibenzoxepins Tetracyclic antidepressants Antipsychotics/dopamine D2 receptor antagonists or partial agonists: Benzamides Benzimidazoles Benzisothiazoles Benzisoxazoles Butyrophenones Diphenylbutylpiperidines Phenylpiperazines Tricyclics Dibenzazepines Dibenzodiazepines Dibenzothiazepines Dibenzothiepins Dibenzoxazepines Phenothiazines Thienobenzodiazepines Mood stabilizers/anticonvulsants: Gabapentinoids Tricyclics Dibenzazepines Valproates
Others	Nootropics: Racetams Phenylpiracetams Miscellaneous: 3-Benzazepines Adamantanes Catecholamines Tetrahydroisoquinolines Yohimbans

Authority control databases
International	GND
National	United States Israel
Other	Yale LUX

Retrieved from "https://en.wikipedia.org/w/index.php?title=Benzamide&oldid=1329177751" Categories:

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• Phenyl compounds

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• Multiple chemicals in an infobox that need indexing
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