MarketBenzocaine
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Benzocaine

Benzocaine, sold under the brand name Orajel amongst others, is a local anesthetic, belonging to the amino ester drug class, commonly used as a topical painkiller or in cough drops. It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is combined with antipyrine to form A/B ear drops. In the US, products containing benzocaine for oral application are contraindicated in children younger than two years old.

Medical uses
Benzocaine is indicated to treat a variety of pain-related conditions. It may be used for: • Local anesthesia of oral and pharyngeal mucous membranes (sore throat, cold sores, mouth ulcers, toothache, sore gums, denture irritation) • Otic pain (earache) • Relief of skin pain caused by sunburn, ingrown toenails, hemorrhoids, Examples of combination medications of benzocaine include: • Antipyrine-benzocaine otic consists of antipyrine and benzocaine, and is used to relieve ear pain and remove earwax. • Cepacol consists of menthol and benzocaine, and is used to treat sore throat. • A solution of benzocaine and menthol is marketed for the treatment of bee stings, mosquito bites, jellyfish stings, and other insect bites Other uses Benzocaine is used as a key ingredient in numerous pharmaceuticals: • Some glycerol-based ear medications for use in removing excess wax as well as relieving ear conditions such as otitis media and swimmer's ear. • Some previous diet products such as Ayds. • Some condoms designed to prevent premature ejaculation. Benzocaine largely inhibits sensitivity on the penis, and can allow for an erection to be maintained longer (in a continuous act) by delaying ejaculation. Conversely, an erection will also fade faster if stimulus is interrupted. • Benzocaine mucoadhesive patches have been used in reducing orthodontic pain. • In Poland it is included, together with menthol and zinc oxide, in the liquid powder (not to be confused with the liquid face powder) used mainly after mosquito bites. Today's ready-made Pudroderm was once used there as pharmaceutical compound. Available forms Benzocaine can come in a variety of preparations including: Oral preparations: • Lozenges (ex. Cepacol, Mycinettes) • Throat Spray (ex. Ultra Chloraseptic) Topical preparations: • Aerosol (ex. Topex) • Gel (ex. Orajel, Kank-A) • Paste (ex. Orabase) • Cream (ex. Lanacane - active ingredient 3% Benzocaine) Otic preparations: • Solution (ex. Allergen) ==Side effects==
Side effects
Benzocaine is generally well tolerated and non-toxic when applied topically as recommended. However, there have been reports of serious, life-threatening adverse effects (e.g., seizures, coma, irregular heart beat, respiratory depression) with over-application of topical products or when applying topical products that contain high concentrations of benzocaine to the skin. The topical use of higher concentration (10–20%) benzocaine products applied to the mouth or mucous membranes has been found to be a cause of methemoglobinemia, a disorder in which the amount of oxygen carried by the blood is greatly reduced. Benzocaine may cause allergic reactions. These include: • Contact dermatitis (redness and itchiness) • Anaphylaxis (rare) ==Chemistry==
Chemistry
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 88–92 °C, and the boiling point is about 310 °C. The density of benzocaine is 1.17 g/cm3. Synthesis Benzocaine can be prepared by esterification using 4-aminobenzoic acid and ethanol. It can also be prepared by reduction of ethyl 4-nitrobenzoate to the amine. In industrial practice, the reducing agent is usually iron and water in the presence of a little acid. ==History==
History
Benzocaine was first synthesized in 1890 by the German chemist Eduard Ritsert (1859–1946), in the town of Eberbach and introduced to the market in 1902 under the name "Anästhesin". == Society and culture ==
Society and culture
Benzocaine is found, particularly in Britain, as an additive in street cocaine and also as a bulking agent in "legal highs". Benzocaine gives a numbing effect similar to cocaine and as a bulking and binding agent it can not be detected once mixed. It is the most popular cutting agent worldwide. ==Veterinary uses==
Veterinary uses
Bath solutions of benzocaine and its derivatives are commonly used to anesthetize amphibians for surgery. Benzocaine-based anesthetics are potent and highly effective for both anesthesia and euthanasia in amphibians. == References ==
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