ethyl 4-aminobenzoate

• ChemBase ID: 957
• Molecular Formular: C9H11NO2
• Molecular Mass: 165.18914
• Monoisotopic Mass: 165.0789786
• SMILES: O(C(=O)c1ccc(N)cc1)CC
• Canonical SMILES: CCOC(=O)c1ccc(cc1)N
• InChI: InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
• InChIKey: BLFLLBZGZJTVJG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 4-aminobenzoate
• IUPAC Traditional name: benzocaine
• Brand Name: Aethoform; Amben Ethyl Ester; Americaine; Anaesthan-Syngala; Anaesthesin; Anaesthin; Anestezin; Anesthesin; Anesthesine; Anesthone; Baby Anbesol; Dermoplast; Ethoform; Hurricaine; Identhesin; Keloform; Norcain; Norcaine; Ora-Jel; Orthesin; Parathesin; Parathesine; Solu H; Topcaine; Anbesol, Cepacol, Lanacane
• Synonyms: Ethyl Aminobenzoate; Ethylester Kyseliny P-Aminobenzoove; Ethyl P-Aminophenylcarboxylate; Ethyl P-Aminobenzoate; P-Aminobenzoic Acid, Ethyl Ester; P-Carbethoxyaniline; P-Ethoxycarboxylic Aniline; Benzocaine; Benzocaine; ethyl 4-aminobenzoate; Benzocainum; p-Aminobenzoic Acid Ethyl Ester; (p-(Ethoxycarbonyl)phenylamine; 4-(Ethoxycarbonyl)aniline; 4-(Ethoxycarbonyl)phenylamine; 4-Carbethoxyaniline; Aethoform; Amben Ethyl Ester; Americaine; Anaesthan-syngala; Benzocaine(See B197952 for Labelled); H-4-Abz-OEt; Ethyl 4-aminobenzoate; Benzocaine solution; 4-Aminobenzoic acid ethyl ester; Benzocaine; ETHYL p-AMINOBENZOATE; Ethyl 4-aminobenzoate; 4-氨基苯甲酸乙酯; 对氨基苯甲酸乙酯; 苯佐卡因; 苯佐卡因; 苯佐卡因 溶液; 4-氨基苯甲酸乙酯

Database IDs

• CAS Number: 94-09-7
• EC Number: 200-659-6; 202-303-5
• MDL Number: MFCD00007892
• Beilstein Number: 638434
• Merck Index: 141086
• PubChem SID: 46508891; 24894416; 24845986; 24847117; 24891975; 160964420
• PubChem CID: 2337
• CHEBI ID: 116735
• ATC CODE: N01BA05; QN01AX92; C05AD03; R02AD01; D04AB04
• CHEMBL: 278172
• Chemspider ID: 13854242
• DrugBank ID: DB01086
• KEGG ID: D00552
• Unique Ingredient Identifier: U3RSY48JW5
• Wikipedia Title: Benzocaine

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.5037898
• LogD (pH = 7.4): 1.5045946
• Log P: 1.5046048
• Molar Refractivity: 47.5323 cm^3
• Polarizability: 17.72883 Å^3
• Polar Surface Area: 52.32 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.2
• LOG S: -1.76
• Solubility (Water): 2.85e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1310 mg/L; Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 84-86°C; 88-90 °C; 88-90 °C(lit.); 88-90°C; 88-92°C
• Boiling Point: 310°C
• Flash Point: >110°C(230°F); 11 °C; 51.8 °F
• Hydrophobicity(logP): 1.6

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: DG2450000
• European Hazard Symbols: Flammable (F); Toxic (T); Irritant (Xi)
• UN Number: 1230
• German water hazard class: 1; 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25; 36-43
• Safety Statements: 24-26-37; 7-16-36/37-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301-H311-H331-H370; H319-H317
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311; P261-P280-P305+P351+P338-P302+P352-P321-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US); Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• RID/ADR: UN 1230 3/PG 2
• Storage Temperature: 2-8°C; room temp

Pharmacology Properties

• Target: Others
• Admin Routes: Topical
• Pregnancy Category: C (US)

Product Information

• Purity: ≥98%; ≥99.0%; ≥99.0% (HPLC); 98%
• Concentration: 1.0 mg/mL±5% in methanol
• Grade: certified reference material; drug standard; Ph Eur; purum; SAJ first grade
• Salt Data: Free Base
• Packaging: pkg of 1 g
• Loss on Drying: ≤0.5% loss on drying, 20 °C (HV)
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Pharmacopeia Traceability: traceable to USP 1054000
• Linear Formula: H2NC6H4CO2C2H5
• Empirical Formula (Hill Notation): C9H11NO2

DETAILS

MP Biomedicals - 02157967

Crystalline

DrugBank - DB01086

• Drug Groups: approved
• Description: A surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings. [PubChem]
• Indication: For general use as a lubricant and topical anesthetic on esophagus, larynx, mouth, nasal cavity, rectum, respiratory tract or trachea, urinary tract, vagina. It is also used to suppress gag reflex.
• Pharmacology: Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter analgesic ointments. It is also indicated for general use as a lubricant and topical anesthetic on intratracheal catheters and pharyngeal and nasal airways to obtund the pharyngeal and tracheal reflexes; on nasogastric and endoscopic tubes; urinary catheters; laryngoscopes; proctoscopes; sigmoidoscopes and vaginal specula.
• Toxicity: LD₅₀=3040 mg/kg (rat, oral)
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - PHR1158

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.

Sigma Aldrich - 112909

Packaging
100, 500 g in poly bottle
5 g in glass bottle

Toronto Research Chemicals - B202970

Benzocaine is used as an anesthetic (local).

REFERENCES

• Kholod, Y., et al.: Environ. Sci. Technol., 43, 9208 (2009)
• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)
• Perez-Garrido, Alfonso; Helguera, A., et al.: J. Pharm. Sci., 98, 4557 (2009)
• Onoue, S., et al.: J. Pharm. Sci., 98, 3647 (2009)