Pramocaine (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway. Before the advent of motorized transportation, they also provided accomm ...

and BAN, also known as pramoxine or pramoxine HCl) is a

topical anesthetic A topical anesthetic is a local anesthetic that is used to numb the surface of a body part. They can be used to numb any area of the skin as well as the front of the eyeball, the inside of the nose, ear or throat, the anus and the genital area. ...

discovered at

Abbott Laboratories Abbott Laboratories is an American multinational medical devices and health care company with headquarters in Abbott Park, Illinois, in the United States. The company was founded by Chicago physician Wallace Calvin Abbott in 1888 to formulate k ...

in 1953 and used as an

antipruritic Antipruritics, abirritants, or anti-itch drugs, are medications that inhibit itching (Latin: ''pruritus''). Itching is often associated with sunburns, allergic reactions, eczema, psoriasis, chickenpox, Fungal infection in animals, fungal infections ...

. During research and development, pramocaine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent. Pharmacologic study revealed it to be potent and of low acute and subacute toxicity, well tolerated by most mucous membranes and of a low sensitizing index in humans. Like other

local anesthetics A local anesthetic (LA) is a medication that causes absence of all sense, sensation (including pain) in a specific body part without loss of consciousness, providing local anesthesia, as opposed to a general anesthetic, which eliminates all sen ...

, pramocaine decreases the permeability of neuronal membranes to sodium ions, blocking both initiation and conduction of nerve impulses. Depolarization and repolarization of excitable neural membranes is thus inhibited, leading to numbness.

Use

Topical anesthetics are used to relieve pain and itching caused by conditions such as

sunburn Sunburn is a form of radiation burn that affects living tissue, such as skin, that results from an overexposure to ultraviolet (UV) radiation, usually from the Sun. Common symptoms in humans and other animals include red or reddish skin tha ...

or other minor burns, insect bites or stings,

poison ivy Poison ivy is a type of allergenic plant in the genus '' Toxicodendron'' native to Asia and North America. Formerly considered a single species, '' Toxicodendron radicans'', poison ivies are now generally treated as a complex of three separate s ...

poison oak Poison oak refers to two plant species in the genus '' Toxicodendron,'' both of which can cause skin irritation: *'' Toxicodendron diversilobum'' or Pacific poison oak, found in western North America *'' Toxicodendron pubescens'' or Atlantic po ...

poison sumac ''Toxicodendron vernix'', commonly known as poison sumac, or swamp-sumach, is a woody shrub or small tree growing to tall. It was previously known as ''Rhus vernix''. This plant is also known as thunderwood, particularly where it occurs in the ...

, and minor cuts and scratches. The hydrochloride

salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...

form of pramocaine is water-soluble. Pramocaine is a common component of

over the counter Over-the-counter (OTC) drugs are medicines sold directly to a consumer without a requirement for a prescription from a healthcare professional, as opposed to prescription drugs, which may be supplied only to consumers possessing a valid pres ...

hemorrhoid Hemorrhoids (or haemorrhoids), also known as piles, are vascular structures in the anal canal. In their normal state, they are cushions that help with stool control. They become a disease when swollen or inflamed; the unqualified term ''h ...

preparations. Pramocaine is also included in some topical antibiotics like Neosporin Plus Pain Relief used to treat or prevent infections due to its pain relieving effects. However, there is no additional antibiotic effect compared to antibiotics without pramocaine.

Synthesis

The ether formation between

hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para' ...

(1) and 1-bromobutane (2) gives 4-butoxyphenol 22-94-1(3). Alkylation with 4-(3-chloropropyl)morpholine 7616-74-7(4) gives pramocaine (5).

References

{{Antipruritics Local anesthetics 4-Morpholinyl compounds Phenol ethers

Use

Synthesis

See also

References