Benzocaine

Alias: H-4-Abz-OEt; NSC-4688; NSC4688; NSC 41531; trade name Orajel amongst others
Cat No.:V1656 Purity: ≥98%
Benzocaine (H-4-Abz-OEt; NSC-4688; NSC-41531; tradename Orajel among others), the ethyl ester of p-aminobenzoic acid (PABA), is a local anesthetic that has been widely used as a topical pain reliever or in cough drops.
Benzocaine Chemical Structure CAS No.: 94-09-7
Product category: Sodium Channel
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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2g
5g
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Other Forms of Benzocaine:

  • Benzocaine-d4 (Benzocaine d4)
  • Benzocaine-(ethyl-d5) (Benzocaine d5)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Benzocaine (H-4-Abz-OEt; NSC-4688; NSC-41531; trade name Orajel among others), the ethyl ester of p-aminobenzoic acid (PABA), is a local anesthetic that has been widely used as a topical pain reliever or in cough drops. Benzocaine acts by reversibly inactivating voltage-dependent sodium channels. It is the active ingredient in many OTC anesthetic ointments (e.g. products for oral ulcers). It is also used in combination with antipyrine as A/B otic drops to relieve ear pain and to remove earwax.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Benzocaine blocks μ1 wild-type Na+ currents in a dose-dependent Manner. The Benzocaine concentration that inhibits 50% of Na+ currents (IC50) is estimated to be about 0.8 mM when a test potential of +30 mV is applied. The slope of the h∞ curve is also significantly reduced by benzocaine (from 6.6 to 9.9 mV). Mutation of μ1-N1584A also significantly increases the potency of Benzocaine. At 1 mM, Benzocaine blocks about 55% of wild-type Na+ current but about 95% of μ1-N1584A mutant current. Benzocaine also appears to bind more strongly to its LA receptor in the N1584A mutant than in the wild type[1]. The inhibition of Ca2+ uptake occurs at lower Benzocaine concentration (IC50=40.3±1.2mM) than that affecting the enzymatic activity[2].
ln Vivo
Dogs, domestic shorthair cats, Sprague-Dawley rats, Long-Evans rats, ferrets, rhesus monkeys, cynomolgus monkeys, owl monkeys, New Zealand White rabbits, miniature pigs, ICR mice, C3H mice, and C57BL/10SnJ mice are among the species to which benzocaine is applied topically. A 2-second spray is administered to the mucous membranes of the nasopharynx for an estimated dose of 56 mg to all animals, with the exception of mice and rats. An excessive amount of fluid is sprayed over the oral mucous membranes of rodents in a two-second burst. A few months later, the study is conducted again on dogs to confirm the poor response. Most studied animals show a reaction to benzocaine spray, with a peak response occurring 15–30 minutes after dosing[3].
Animal Protocol

Guinea pig
References
[1]. Wang GK et al. A common local anesthetic receptor for benzocaine and etidocaine in voltage-gated mu1 Na+ channels. Pflugers Arch. 1998 Jan;435(2):293-302.
[2]. Davis JA, et al. Benzocaine-induced methemoglobinemia attributed to topical application of the anesthetic in several laboratory animal species. Am J Vet Res. 1993 Aug;54(8):1322-6.
[3]. Di Croce D et al. Drug action of benzocaine on the sarcoplasmic reticulum Ca-ATPase from fast-twitch skeletal muscle. Naunyn Schmiedebergs Arch Pharmacol. 2015 Nov;388(11):1163-70.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H11NO2
Molecular Weight
165.19
CAS #
94-09-7
SMILES
O=C(OCC)C1=CC=C(N)C=C1
InChi Key
BLFLLBZGZJTVJG-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
Chemical Name
Benzoic acid, p-amino-, ethyl ester
Synonyms
H-4-Abz-OEt; NSC-4688; NSC4688; NSC 41531; trade name Orajel amongst others
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO:33 mg/mL (199.8 mM)
Water:<1 mg/mL
Ethanol:33 mg/mL (199.8 mM)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.0536 mL 30.2682 mL 60.5364 mL
5 mM 1.2107 mL 6.0536 mL 12.1073 mL
10 mM 0.6054 mL 3.0268 mL 6.0536 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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