637-58-1

Basic information

• Product Name: Pramoxine hydrochloride
• Synonyms: Morpholine, 4-[3-(4-butoxyphenoxy)propyl]-, hydrochloride (1:1);Pramoxine hydrochloride 4-n-Butoxyphenyl gamma-morpholinopropyl ether hydrochloride;Pramoxine Hydrochloride (400 mg);4-(3-(p-butoxyphenoxy)propyl)-morpholinhydrochloride;gamma-morpholinopropyl4-n-butoxyphenyletherhydrochloride;p-butoxyphenylgamma-morpholinopropyletherhydrochloride;proctofoam;PRAMOXINE HCL
• CAS NO: 637-58-1
• Molecular Formula: C₁₇H₂₇NO₃*ClH
• Molecular Weight: 329.86
• EINECS: 211-293-1
• Product Categories: YUTOPAR
• Mol File: 637-58-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 181-183°
• Boiling Point: 427 °C at 760 mmHg
• Flash Point: 123.5 °C
• Appearance: White or off white crystalline powder
• Vapor Pressure: 1.7E-07mmHg at 25°C
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Pramoxine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Pramoxine hydrochloride(637-58-1)
• EPA Substance Registry System: Pramoxine hydrochloride(637-58-1)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: QD8750000
• Hazardous Substances Data: 637-58-1(Hazardous Substances Data)

Usage

Description

Pramoxine, also known as pramocaine, is different from other local anesthetic compounds in chemical structure. Active groups which are carboxylic acid derivatives like ester and amide are not present in this molecule. The drug molecule consists of ether functional groups that are much less active on a chemical level. The presence of the free radical morpholine in this compound is the cause of the reduction of the factor of toxicity and pharmacological activity. In pramoxine, toxicity is reduced but the local anesthetic affect is maintained.Pramoxine Hydrochloride is the hydrochloride salt form of pramoxine, It is a common, over-the-counter anti-itch ingredient that provides temporary relief from itching caused by insect bites, minor skin irritations, poison ivy, sunburn and more.

Uses

Different sources of media describe the Uses of 637-58-1 differently. You can refer to the following data:
1. slows growth of unwanted facial hair
2. Pramoxine Hydrochloride is used as a local anaesthetic and often in anti-itch formulations.

Indications

Pramoxine hydrochloride (Itch-X, PrameGel, Prax, Tronothane, AmLactin AP) is a local anesthetic that is structurally similar to dyclonine and unrelated to the esteror amide-type compounds.Apply to affected area t.i.d. to q.i.d., as directed by a physician. Useful for patients sensitive to ester and/or amide anesthetics. Onset of anesthesia is within minutes. Duration of anesthesia is 2 to 4 hours.

Therapeutic Function

Local anesthetic

Clinical Use

Pramoxine is an amino-ether which, like dyclonine, is used as a topical agent in the form of its hydrochloride. Pramoxine hydrochloride may be used for anaesthesia of minor skin wounds and the relief of haemomhoids and other anorectal disorders.The drug is an ingredient of many proprietary topical products, and the U.S.P. has official cream and gel formulations.

Veterinary Drugs and Treatments

A surface and local anesthetic to peripheral nerves not related structurally to procaine-type anesthetics, pramoxine is often added to other topicals to reduce pain and/or itching.

Mode of action

Pramoxine hydrochloride is the hydrochloride salt form of pramoxine, a morpholine derivative with local anesthetic property. Pramocaine hydrochloride decreases the permeability of the neuronal membrane to sodium ions by reversibly binding to and inhibiting voltage-gated sodium channels. This results in stabilization of the membrane and, thereby inhibiting the ionic fluxes required for membrane depolarization, hence resulting in the failure to initiate a propagated action potential and subsequent conduction blockade.

InChI:InChI=1/C17H27NO3.ClH/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;1H

Synthetic route

3-morpholin-4-ylpropan-1-ol (4441-30-9) + 1-bromo-4-butoxybenzene (39969-57-8) → pramoxine hydrochloride (637-58-1)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 5h; Reflux;	82.61%

Upstream product

• 4441-30-9 3-morpholin-4-ylpropan-1-ol 
• 39969-57-8 1-bromo-4-butoxybenzene 

Relevant articles and documents

A pramoxine hydrochloride preparing method

The invention belongs to the technical field of medicine synthesis, and particularly relates to a pramoxine hydrochloride preparing method. The method includes reacting p-bromophenol and 1-bromobutaneunder catalytic functions of an alkali to prepare an intermediate that is 1-bromo-4-tert-butoxybenzene; synthesizing pramoxine having a base group from the 1-bromo-4-tert-butoxybenzene and 3-morpholinopropanol with the existence of a strong alkali; and subjecting the pramoxine having the base group to salification to obtain the pramoxine hydrochloride. The yield of the pramoxine hydrochloride prepared by the method is higher than 80%, and liquid-phase purity of the prepared pramoxine hydrochloride is higher than 99.8%. The method is used for preparing the pramoxine hydrochloride, and is simple to operate and high in yield, raw materials are easily available, product purity is high, the cost is low, and pollution is low.