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 accommo ...

and

BAN Ban, or BAN, may refer to: Law * Ban (law), a decree that prohibits something, sometimes a form of censorship, being denied from entering or using the place/item ** Imperial ban (''Reichsacht''), a form of outlawry in the medieval Holy Roman ...

, also known as pramoxine or pramoxine HCI) 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. Top ...

discovered at

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

in 1953 and used as an

antipruritic Antipruritics, abirritants, or anti-itch drugs, are medications that inhibit the itching (Latin: ''pruritus'') often associated with sunburns, allergic reactions, eczema, psoriasis, chickenpox, fungal infections, insect bites and stings like those ...

. 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 pain sensation. In the context of surgery, a local anesthetic creates an absence of pain in a specific location of the body without a loss of consciousness, as opposed to a general an ...

, 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 or other minor burns, insect bites or stings, poison ivy,

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

, poison sumac, and minor cuts and scratches. The popular itch creams

Gold Bond Gold Bond is a brand of over-the-counter skin care products produced by Chattem of Chattanooga, Tennessee, now a subsidiary of the French pharmaceutical company Sanofi. It is available as both a powder and a topical cream. Gold Bond is used to cur ...

and some forms of

calamine lotion Calamine, also known as calamine lotion, is a medication used to treat mild itchiness. This includes from sunburn, insect bites, poison ivy, poison oak, and other mild skin conditions. It may also help dry out skin irritation. It is applied ...

use pramocaine hydrochloride to numb sensitive skin, as does the pain relief variant of Neosporin and some formulations of Sarna. The hydrochloride

salt Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quantitie ...

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

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 ''hemo ...

preparations.

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 1-Bromobutane is the organobromine compound with the formula CH3(CH2)3Br. It is a colorless liquid, although impure samples appear yellowish. It is insoluble in water, but soluble in organic solvents. It is a primarily used as a source of the buty ...

(2) gives 4-butoxyphenol 22-94-1(3). Alkylation with 3-chloropropoylmorpholine 7616-74-7(4) gives pramocaine (5).

References

{{Antipruritics Local anesthetics 4-Morpholinyl compunds Phenol ethers

Use

Synthesis

See also

References