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Benzocaine

Benzocaine Structure
CAS No.
94-09-7
Chemical Name:
Benzocaine
Synonyms
ETHYL 4-AMINOBENZOATE;Benzocaine base;ethyl aminobenzoate;4-AMINOBENZOIC ACID ETHYL ESTER;Anestezin;Benzocaine, USP, EP;ETHYL P-AMINOBENZOATE;NSC 4688;anesthesin;benzociane
CBNumber:
CB1217951
Molecular Formula:
C9H11NO2
Molecular Weight:
165.19
MOL File:
94-09-7.mol
MSDS File:
SDS
Modify Date:
2024/8/13 17:19:14

Benzocaine Properties

Melting point 88-90 °C
Boiling point 172 °C (12.7517 mmHg)
Density 1.17
refractive index 1.5600 (estimate)
Flash point 172°C/13mm
storage temp. 2-8°C
solubility alcohol: soluble1 gm in 5 ml
form Crystalline Powder
pka 2.5(at 25℃)
color White
Odor odorless
Water Solubility Soluble in ethanol, chloroform, ethyl ether and dilute acids. Sparingly soluble in water
Merck 14,1086
BRN 638434
Stability Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey BLFLLBZGZJTVJG-UHFFFAOYSA-N
LogP 1.860
CAS DataBase Reference 94-09-7(CAS DataBase Reference)
NIST Chemistry Reference Benzoic acid, 4-amino-, ethyl ester(94-09-7)
EPA Substance Registry System Benzocaine (94-09-7)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07
Signal word  Warning
Hazard statements  H317
Precautionary statements  P261-P272-P280-P302+P352-P333+P313-P362+P364
Hazard Codes  Xi,T,F
Risk Statements  43-36/37/38-39/23/24/25-23/24/25-11
Safety Statements  22-24/25-37/39-26-24-45-36/37-16-7
RIDADR  3077
WGK Germany  2
RTECS  DG2450000
TSCA  Yes
HazardClass  9
PackingGroup  III
HS Code  29224995
Toxicity LD50 oral in rat: 3042mg/kg
NFPA 704
0
2 0

Benzocaine price More Price(13)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) E1501 Benzocaine ≥99% (HPLC) 94-09-7 100G ₹4611.45 2022-06-14 Buy
Sigma-Aldrich(India) PHR1158 Benzocaine Pharmaceutical Secondary Standard; Certified Reference Material 94-09-7 1G ₹8356.9 2022-06-14 Buy
Sigma-Aldrich(India) E1501 Benzocaine ≥99% (HPLC) 94-09-7 500G ₹9103.83 2022-06-14 Buy
Sigma-Aldrich(India) 112909 Ethyl 4-aminobenzoate 98% 94-09-7 5G ₹996.99 2022-06-14 Buy
Sigma-Aldrich(India) 112909 Ethyl 4-aminobenzoate 98% 94-09-7 100G ₹2035.1 2022-06-14 Buy
Product number Packaging Price Buy
E1501 100G ₹4611.45 Buy
PHR1158 1G ₹8356.9 Buy
E1501 500G ₹9103.83 Buy
112909 5G ₹996.99 Buy
112909 100G ₹2035.1 Buy

Benzocaine Chemical Properties,Uses,Production

Description

Benzocaine (ethyl p-aminobenzoate) is used topically by itself or in combination with menthol or phenol in nonprescription dosage forms such as gels, creams, ointments, lotions, aerosols, and lozenges to relieve pain or irritation caused by such conditions as sunburn, insect bites, toothache, teething, cold sores or canker sores in or around the mouth, and fever blisters. Benzocaine is a lipophilic local anesthetic agent with a short duration of action.
Like most amino ester-type local anesthetics, it is easily hydrolyzed by plasma cholinesterase. Because of its low pKa, however, it is un-ionized under most physiological conditions and, therefore, can only bind to the lipid side of the local anesthetic receptor. It also can easily cross membranes into systemic circulation to cause systemic toxicities. Furthermore, being a PABA derivative, it has similar allergenic properties to procaine and is contraindicated with sulfonamide antibacterial agents.

Chemical Properties

Benzocaine is a white odourless needle-like crystal, slightly soluble in water and easily soluble in organic solvents. For example: ethanol, chloroform, ether, soluble in almond oil, olive oil.

Uses

Benzocaine is used as an anesthetic (Local and topical) that in products such as burn and sunburn remedies, hemorrhoidal creams, suppositories, creams for treatment of poison ivy, oral and gingival products, sore-throat sprays/lozenges, astringents, appetite suppressants, callus and wart remedies, athlete's-foot remedies, toothache- and denture-irritation products.

Definition

ChEBI: Benzocaine is a benzoate ester having 4-aminobenzoic acid as the acid component and ethanol as the alcohol component. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina. It has a role as a topical anaesthetic, an antipruritic drug, an allergen and a sensitiser. It is a benzoate ester and a substituted aniline.

Biological Functions

Benzocaine is a PABA derivative used primarily for topical application to skin and mucous membranes. Its low aqueous solubility allows it to stay at the site of application for long periods. Its minimal rate of absorption after topical administration is associated with a low incidence of systemic toxicity. Benzocaine is contraindicated in patients with known sensitivity to ester-linked anesthetics or PABA-containing compounds.

General Description

Benzocaine is a unique local anesthetic because it does notcontain a tertiary amine. The pKa of the aromatic amine is 3.5ensuring that benzocaine is uncharged at physiological pH.Because it is uncharged, it is not water soluble but is ideal fortopical applications. The onset of action is within 30 secondsand the duration of drug action is 10 to 15 minutes.

Clinical Use

Benzocaine is used for endoscopy, bronchoscopy, and topicalanesthesia. Benzocaine is available as a 20% solution topicalspray, in a 1% gel for mucous membrane application, and a14% glycerin suspension for topical use in the outer ear.Toxicity to benzocaine can occur when the topical doseexceeds 200 to 300 mg resulting in methemoglobinemia.Infants and children are more susceptible to this and methemoglobinemiahas been reported after benzocaine lubricationof endotracheal tubes and after topical administration to treata painful diaper rash.

Safety Profile

Poison by ingestion and intraperitoneal routes. Human systemic effects by rectal route: methemoglobinemia/carboxyhemoglobinem ia in infants. A skin irritant and a mild sensitizer. Local contact may cause contact dermatitis. Used as a topical anesthetic and as a sun-screening agent. When heated to decomposition it emits highly toxic fumes of NOx. See also ETHYL ALCOHOL and ESTERS

Purification Methods

Crystallise Benzocaine from EtOH/H2O or EtOH (m 93-94o), and dry it in air. [Beilstein 14 H 422, 14 IV 1129.]

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Benzocaine (See B197952 for Labelled) Ethyl 4-aMinobenzoate, 98% 500GR (p-(Ethoxycarbonyl)phenylaMine 4-(Ethoxycarbonyl)phenylaMine 4-Aminobenzoic Acid Ethyl Ester Benzocaine The aMino acid ethyl ester Benzocaine solution Ethyl 4-aminobenzoate Vetec(TM) reagent grade, 98% Benzocaine, >=99% Anaesthesin Anaesthin Anesthesine Anesthone Baby Anbesol Benzoic acid, p-amino-, ethyl ester Benzoicacid,4-amino-,ethylester component of Anbesol maximum strength component of Cough-x component of Outgro component of Solarcaine aerosol component of Tympagesic Dermoplast Ethoform Ethyl p-aminophenylcarboxylate Ethylester kyseliny p-aminobenzoove ethylesterkyselinyp-aminobenzoove Hurricaine Identhesin Norcain Norcaine Ora-jel p-(Ethoxycarbonyl)aniline p-amino-benzoicaciethylester Parathesine p-Carbethoxyaniline p-Ethoxycarboxylic aniline Solarcaine Solu H Topcaine Snow Lotus Herb Extract Anaesthesine,Ethyl Aminobenzoate 4-minobenzoic acid ethyl ester AKOS BBS-00003658 4-(Ethoxycarbonyl)aniline 4-amino-benzoicaciethylester 4-Carbethoxyaniline LABOTEST-BB LTBB000527 H-4-ABZ-OET ETHYLAMINOBENZOATE-4 auralgan otic BENZOCAINE benzocaine bp98 BENZOCAINUM parathesin ORTHESIN ETHYL PABA ETHYL-PARA-AMINOBENZOATE PARA-AMINOBENZOICACIDETHYLESTER