pramocaine Chemical Properties

Boiling point:

bp6 196°; bp2.8 183-184°

Density 

1.0112 (rough estimate)

refractive index 

1.5420 (estimate)

pka

7.18±0.10(Predicted)

Water Solubility 

3.574mg/L(22.5 ºC)

CAS DataBase Reference

140-65-8

Safety Information

Toxicity

LD50 in mice (mg/kg): 300 i.p., 900 s.c. (Monash, Gibbs)

pramocaine Usage And Synthesis

Originator

Tronothane, Abbott, US ,1954

Uses

Anesthetic (topical).

Definition

ChEBI: A member of the class of morpholines that is morpholine substituted at the nitrogen atom by a 3-(4-butoxyphenoxy)propyl group.

Manufacturing Process

About 5.6 g of potassium hydroxide is dissolved in about 150 cc of refluxing ethanol, and then about 16.6 g of hydroquinone monobutyl ether is added to the alcoholic solution. When the hydroquinone is dissolved, about 16.3 g of γmorpholinopropyl chloride (dissolved in a small amount of ethanol) is added to the refluxing solution. The solution is refluxed for about 24 hours and then cooled. The product is recovered by filtering the reaction mixture and then removing the solvent by vacuum distillation. The oily residue is acidified and shaken with ether. The acidic phase is made strongly alkaline with 40% sodium hydroxide, and the oil which separates is extracted into ether. The ethereal phase is dried, and the solvent removed by vacuum distillation. The product distills at 183° to 184°C at a pressure of 2.8 mm. The hydrochloride salt of the foregoing base is prepared by dissolving the base in ether and acidifying with hydrochloric acid and is found to have a MP of 181° to 183°C.

brand name

Tronolane (Ross); Tronothane (Abbott).

Therapeutic Function

Local anesthetic

pramocaine(140-65-8)Related Product Information

• Pramoxine hydrochloride
• pramocaine