Pramocaine

Pramocaine

Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682429
Routes of administration	Topical, rectal, Vaginal
ATC code	D04AB07 (WHO) C05AD07 (WHO)
Legal status
Legal status	CA: OTC UK: POM (Prescription only) OTC/POM
Identifiers
IUPAC name 4-[3-(4-butoxyphenoxy)propyl]morpholine
CAS Number	140-65-8 N 637-58-1
PubChem CID	4886
ChemSpider	4717 Y
UNII	068X84E056
ChEBI	CHEBI:8357 Y
ChEMBL	ChEMBL1198 Y
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C17H27NO3
Molar mass	293.401 g/mol
3D model (JSmol)	Interactive image
SMILES O(c2ccc(OCCCN1CCOCC1)cc2)CCCC
InChI InChI=1S/C17H27NO3/c1-2-3-12-20-16-5-7-17(8-6-16)21-13-4-9-18-10-14-19-15-11-18/h5-8H,2-4,9-15H2,1H3 Y Key:DQKXQSGTHWVTAD-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Pramocaine (INN and BAN, also known as pramoxine or pramoxine HCI) is a topical anesthetic discovered at Abbott Laboratories in 1953 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. 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. 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.

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. Pramocaine and dibucaine are also common ingredients in over the counter hemorrhoid preparations.

Synthesis

Pramoxine synthesis:

See also

• Local anesthesia

Notes

Template:Vasoprotectives Template:Antipruritics