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    Benzocaine
    Benzocaine

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1656
    CAS #: 94-09-7Purity ≥98%

    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.

    References: Pflugers Arch. 1998 Jan;435(2):293-302; Biophys Chem. 2000;87(2-3):213-23.

    Related CAS#: 23239-88-5 (HCl)

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    Molecular Weight (MW)165.19 
    FormulaC9H11NO2 
    CAS No.94-09-7 
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 33 mg/mL (199.8 mM) 
    Water: <1 mg/mL
    Ethanol: 33 mg/mL (199.8 mM) 
    Other info

    Chemical Name: Benzoic acid, p-amino-, ethyl ester

    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

    SMILES Code: O=C(OCC)C1=CC=C(N)C=C1

    Synonyms

    H-4-Abz-OEt; NSC-4688; NSC4688; NSC 41531; trade name Orajel amongst others


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    In Vitro

    In vitro activity: Benzocaine blocks µ1 wild-type Na+ currents in a dose-dependent manner with IC50 of 0.8 mM in HEK293T cells. Benzocaine (1 mM) blocks about 55% of wild-type Na+ current but about 95% of µ1-N1584A mutant current. Benzocaine (1 mM) blocks about 55% of wild-type µ1 currents, but about 80% of µ1-I1575A mutant current. Benzocaine results in a biphasic (protective/inductive) concentration-dependent hemolytic effect upon rat erythrocytes, with an effective Benzocaine:lipid molar ratio in the membrane for protection (RePROT), onset of hemolysis (ReSAT) and 100% membrane solubilization (ReSOL) of 1.0:1, 1.1:1 and 1.3:1, respectively. Benzocaine and 4-hydroxybenzoate interact with the open and inactivated channels during repetitive pulses, but during the interpulse the complex dissociates too fast to accumulate sufficient use-dependent block of Na+ currents. Benzocaine (500 μM) reduces the peak and steady-state currents and increases the amplitude of the inactivating component from 21.7% to 30.2% (n=7, P<0.05), so that benzocaine-induced block at the end of pulses to +60 mV averaged 30.9% (n=7). Benzocaine (500 μM) significantly accelerates the initial phase of deactivation (τf=27.2±2.6 ms, n=7, P<0.01), but does not modify the slow phase of tail current decline. Benzocaine binds with high affinity to an intracellular binding site to produce 'agonist' effects and to a low affinity subsite, which is also located in the inner mouth, to produce the blocking effects. Benzocaine and extracellular K(+) interact to modify the voltage-dependence of channel opening.

    In VivoBenzocaine is absorbed rapidly and similarly through both viable and nonviable skin of the hairless guinea pig, the absorption of the two acidic compounds, benzoic acid and PABA, is greater through nonviable skin. 
    Animal modelGuinea pig
    Formulation & Dosage
    References

    Pflugers Arch. 1998 Jan;435(2):293-302; Biophys Chem. 2000 Oct 30;87(2-3):213-23; Biophys Chem. 2000 Oct 30;87(2-3):213-23. 


    These protocols are for reference only. InvivoChem does not independently validate these methods.

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