3022 Benzocaine Benzocaine is a surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings. Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter analgesic ointments. Benzocaine is an ester, a compound made from the organic acid PABA (para-aminobenzoic acid) and ethanol. The process in which this ester is created is known as Fischer esterification. 94-09-7 2337 C9H11NO2 165.078980 White powder. 92°C 310°C 1310 mg/L (at 30°C) Topical; oral Benzocaine binds to sodium channels and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions. Depolarization of the neuronal membrane is inhibited thereby blocking the initiation and conduction of nerve impulses. Hepatic (to a lesser extent) and plasma via hydrolysis by cholinesterase. Excretion trhough urine (as metabolites) (L1861) LD50: 3040 mg/kg (Oral, Rat) (A308) No indication of carcinogenicity to humans (not listed by IARC). Local anesthetic commonly used as a topical pain reliever. Benzocaine is used as a key ingredient in numerous pharmecuticals: Phenazone, an anti-inflammatory; some glycerol-based ear medications for use in removing excess wax as well as relieving ear conditions such as Otitis Media and swimmers ear; some previous diet products such as Ayds; some condoms designed to prevent premature ejaculation. Benzocaine acts to desensitize the penis, and theoretically allows an erection to be maintained. [Wikipedia] Allergic reactions occur with ester local anaesthetics (like benzocaine) because of the PABA structure. Benzocaine also is a well-known cause of methemoglobinemia. [Wikipedia]. Methemoglobinemia has been reported with benzocaine in oral overdose. (L1861) Treatment is primarily symptomatic and supportive; termination of anesthesia by pneumatic tourniquet inflation should be attempted when the agent is administered by infiltration or regional injection. Methemoglobinemia may be treated with methylene blue, 1-2 mg/kg I.V. infused over several minutes. Seizures commonly respond to diazepam, while hypotension responds to I.V. fluids and Trendelenburg positioning. Bradyarrhythmias (when the heart rate is <60) can be treated with I.V., I.M., or SubQ atropine 15 mcg/kg. With the development of metabolic acidosis, I.V. sodium bicarbonate 0.5-2 mEq/kg and ventilatory assistance should be instituted. (L1861) 2009-07-21T20:28:20Z 2014-12-24T20:25:54Z Benzocaine C07527 116735 Benzocaine DB01086 1756 true CCOC(=O)C1=CC=C(N)C=C1 C9H11NO2 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 165.1891 165.078978601 Exogenous Solid 1.86 HMDB04992 CHEMBL278172 13854242