Benzamide

Names
Preferred IUPAC name

Benzamide[1]

Systematic IUPAC name

Benzenecarboxamide

Other names

Benzoic acid amide
Phenyl carboxamide
Benzoylamide

Identifiers

CAS Number

* 55-21-0 Y

3D model (JSmol)

* Interactive image
* Interactive image

3DMet  |

* B01116

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) Y

Key: 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)  |

Flash point | 180 °C (356 °F; 453 K)

Autoignition
temperature

| > 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
* Salverine
* procainamide

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
* aminohippuric acid
* Chidamide
* Denipride
* Entinostat
* Eticlopride
* imatinib
* Mocetinostat
* Procarbazine
* Pyramide (pyridinyl ethylbenzimide)[7]
* Raclopride
* Sunifiram

## See also[edit]

* ATC code N05AL Benzamides – Therapeutic subgroup for alphanumeric classification of drugs

## 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. p. 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.
7. ^ Kent, James A.; Singh, K. N.; Merchant, Kavita (2012). "The Agrochemical Industry, Annex 17.1". In Kent, James A. (ed.). Handbook of Industrial Chemistry and Biotechnology. New York: Springer Verlag. pp. 643–698. doi:10.1007/978-1-4614-4259-2_17. ISBN 9781461442592. OCLC 1097100876. Archived from the original on 2022-10-11. Retrieved 2022-10-11.

## 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
* 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

* 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
* Metoclopramide
* 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|

* Alizapride
* Bromopride
* Chlorpromazine
* Clebopride
* Domperidone
* Haloperidol
* Hydroxyzine
* Itopride
* 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

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|

* Oxyphencyclimine
* Camylofin
* Mebeverine
* Trimebutine
* Rociverine
* Dicycloverine
* Dihexyverine
* Difemerine
* Piperidolate

|

Quaternary
ammonium
compounds|

* Benzilone
* Mepenzolate
* Pipenzolate
* Glycopyrronium
* Oxyphenonium
* Penthienate
* Methantheline
* Propantheline
* Otilonium
* Tridihexethyl
* Isopropamide
* Hexocyclium
* Poldine
* Bevonium
* Diphemanil
* Tiemonium
* Prifinium
* Timepidium
* Fenpiverinium

Phosphodiesterase
inhibitors|

* Papaverine
* Drotaverine
* Moxaverine

Acting on
serotonin receptors|

* 5-HT3 antagonists
* Alosetron
* Cilansetron
* 5-HT4 agonists
* Mosapride

Other|

* Alverine
* Caroverine
* Chlorbenzoxamine
* Diisopromine
* Dimethylaminopropionylphenothiazine
* Fenpiprane
* Fenoverine
* 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
* Methylatropine
* Fentonium bromide
* Cimetropium bromide

Propulsives|

* Primarily dopamine antagonists
* Metoclopramide/Bromopride
* Clebopride
* Domperidone
* Alizapride
* 5-HT4 agonists
* Cinitapride
* Cisapride

* v
* t
* e

Analgesics (N02A, N02B)

Opioids|

| Opiates/opium|

* Codeine#
* +aspirin
* +paracetamol
* Morphine# (+naltrexone)
* Opium
* Laudanum
* Paregoric

|

Semisynthetic|

* Acetyldihydrocodeine
* Benzylmorphine
* Buprenorphine (+naloxone)
* Butorphanol
* Desomorphine
* Diamorphine (heroin)
* 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
* Tilidine
* Tramadol (+celecoxib, +paracetamol)
* Viminol

Paracetamol-type|

* Acetanilide‡
* Bucetin‡
* Butacetin‡
* Paracetamol (acetaminophen)#
* +aspirin/caffeine
* +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 channel
modulators|

| 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§

Potassium openers|

* Flupirtine‡

Myorelaxants|

* Carisoprodol
* Chlorzoxazone
* Cyclobenzaprine
* Mephenoxalone
* Methocarbamol
* Orphenadrine

Others|

* Analgecine
* Analgesic adjuvant
* Bedinvetmab
* Camphor
* Capsaicin
* Clonidine
* Frunevetmab
* Ketamine
* Menthol
* Methoxyflurane
* Phenazopyridine
* Proglumide
* Rimazolium
* Tanezumab

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

Authority control: National |

* Germany
* Israel
* United States

|

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H302]: H302: Harmful if swallowed
*[H341]: H341: Suspected of causing genetic defects
*[P201]: P201: Obtain special instructions before use.
*[P202]: P202: Do not handle until all safety precautions have been read and understood.
*[P264]: P264: Wash ... thoroughly after handling.
*[P270]: P270: Do not eat, drink or smoke when using this product.
*[P281]: P281: Use personal protective equipment as required.
*[P301+P312]: P301+P312: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell.
*[P308+P313]: P308+P313: IF exposed or concerned: Get medical advice/attention.
*[P330]: P330: Rinse mouth.
*[P405]: P405: Store locked up.
*[P501]: P501: Dispose of contents/container to ...
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