Benzocaine, sold under the brand name Orajel among others, is an ester local anesthetic commonly used as a topical pain reliever or in cough drops.
It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is also combined with antipyrine to form A/B otic drops to relieve ear pain and remove earwax.
Benzocaine is the ethyl ester of p-aminobenzoic acid (PABA). It can be prepared from PABA and ethanol by Fischer esterification or via the reduction of ethyl p-nitrobenzoate. Benzocaine is sparingly soluble in water; it is more soluble in dilute acids and very soluble in ethanol, chloroform, and ethyl ether. The melting point of benzocaine is 88–90 °C, and the boiling point is about 310 °C. The density of benzocaine is 1.17 g/cm3.
Benzocaine is commonly found, particularly in Britain, as an impurity in street cocaine and also as a bulking agent in "legal highs". Whilst giving a numbing effect similar to cocaine on users' gums, it does not actually produce the effects of cocaine. Benzocaine was used in synthesis of leteprinim. Treatment of benzocaine with hydrazine leads to aminostimil, a compound related to isoniazid.