Pramocaine

Pramocaine

Pramocaine
Systematic (IUPAC) name
4-[3-(4-butoxyphenoxy)propyl]morpholine
Clinical data
AHFS/Drugs.com
MedlinePlus
Legal status
Routes Topical, rectal, Vaginal
Identifiers
CAS number  N 637-58-1
ATC code D04 C05
PubChem
ChemSpider  YesY
UNII  YesY
ChEBI  YesY
ChEMBL  YesY
Chemical data
Formula C17H27NO3 
Mol. mass 293.401 g/mol
 N   

Pramocaine (INN and BAN, also known as pramoxine or pramoxine HCI) is a topical anesthetic discovered at Abbott Laboratories in 1953[1] and used as an antipruritic. Chemically, it is p-n butoxyphenyl gammamorpholinopropyl ether hydrochloride. During research and development, pramoxine hydrochloride stood out among a series of alkoxy aryl alkamine ethers as an especially good topical local anesthetic agent.[1] 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 man.[1] Like other local anesthetics, paramoxine 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.

The popular itch creams Gold Bond and Calamine Lotion use pramocaine hydrochloride to numb sensitive skin, as does the pain relief variant of Neosporin and some formulations of Sarna. The hydrochloride salt form of pramocaine is water-soluble.

Contents

  • Usage 1
  • Synthesis 2
  • See also 3
  • Notes 4

Usage

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 sumac, and minor cuts and scratches.[2] Pramocaine and dibucaine are also common ingredients in over the counter hemorrhoid preparations.

Synthesis

Pramoxine synthesis:[3]

See also

Notes

  1. ^ a b c Schmidt JL, Blockus LE, Richards RK. The Pharmacology of Pramoxine Hydrochloride: A New Topical Local Anesthetic. Curr Res Anesth Analg. 1953 Nov-Dec;32(6:1):418-25.
  2. ^ "Pramoxine". MedlinePlus Drug Information. National Library of Medicine. September 25, 2013. Retrieved October 9, 2013. 
  3. ^ WILSON, JAMES W. (1951). "ANALGESICS. III. AMINOPHTHALIDYLALKANES". The Journal of Organic Chemistry 16 (5): 792–799.