Structure via PubChem · Public domain (PubChem)
benzocaine
Sign in to saveAlso known as Baby Anbesol, Americaine, Ethyl p-Aminophenylcarboxylate, p-(Ethoxycarbonyl)aniline, p-Ethoxycarboxylic Aniline, Benzocainum, Amben ethyl ester, p-Carbethoxyaniline
Benzocaine, sold under the brand name Orajel amongst others, is a local anesthetic, belonging to the amino ester drug class, commonly used as a topical painkiller or in cough drops. It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is combined with antipyrine to form A/B ear drops. In the US, products containing benzocaine for oral application are contraindicated in children younger than two years old.
OverviewAI-generated
Benzocaine is a chemical compound with the formula C₉H₁₁NO₂. Its IUPAC name is ethyl 4-aminobenzoate. The substance has a mass of 165.079 and a weight of 165.19. It features a melting point of 90.
Chemical properties include an xlogp of 1.9 and a tpsa of 52.3. The molecule contains one hydrogen bond donor and three hydrogen bond acceptors, with a charge of 0. The canonical SMILES notation is CCOC(=O)C1=CC=C(C=C1)N.
Benzocaine is referenced by 548 other encyclopedia articles. A search for the term yields 1692 results in the PubMed database.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.image
- Benzocaine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 200
- Drug.image2
- Benzocaine-from-xtal-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200
- Drug.tradename
- Anbesol, Lanacane, Orajel, others
- Drug.routes_of_administration
- Topical, Oral
- Drug.ATC_prefix
- C05
- Drug.ATC_suffix
- AD03
- Drug.ATC_supplemental
- , , ,
- Drug.legal_AU
- S4
- Drug.legal_AU_comment
- /Schedule 2
- Drug.legal_UK
- GSL, P
- Drug.legal_US
- OTC
- Drug.CAS_number
- 94-09-7
- Drug.PubChem
- 2337
- Drug.DrugBank
- DB01086
via Wikipedia infobox
Chemical data
- Formula
- C9H11NO2
- Molecular weight
- 165.19 g/mol
- IUPAC name
- ethyl 4-aminobenzoate
- SMILES
- CCOC(=O)C1=CC=C(C=C1)N
- InChIKey
- BLFLLBZGZJTVJG-UHFFFAOYSA-N
- XLogP
- 1.9
- Polar surface area
- 52.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
1,692 papers- Benzocaine: Review on a Drug with Unfold Potential.Mini reviews in medicinal chemistry · 2020
- Benzocaine-Associated Methemoglobinemia.American journal of therapeutics · 2018
- Benzocaine-Induced Methemoglobinemia.The Journal of emergency medicine · 2017
- Benzocaine-induced methemoglobinemia in the pediatric population.Journal of pediatric nursing · 2012
- Benzocaine-induced methemoglobinemia.American journal of diseases of children (1960) · 1977
via PubMed
~5 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Other uses
- Available forms
- Side effects
- Chemistry
- Synthesis
- History
- Society and culture
- Veterinary uses
- References
Benzocaine, sold under the brand name Orajel amongst others, is a local anesthetic, belonging to the amino ester drug class, commonly used as a topical painkiller or in cough drops. It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is combined with antipyrine to form A/B ear drops. In the US, products containing benzocaine for oral application are contraindicated in children younger than two years old.
It was first synthesised in 1890 in Germany and approved for medical use in 1902.
Excerpted from Wikipedia’s “benzocaine” article, available under the CC BY-SA 4.0 licence.