(±)-N-(2,6-dimethylphenyl)-2-(ethylpropylamino)butyramide monohydrochloride

(±)-N-(2,6-dimethylphenyl)-2-(ethylpropylamino)butyramide monohydrochloride Property

Melting point:

203-203.5°

storage temp. 

Hygroscopic, Refrigerator, under inert atmosphere

solubility 

DMSO, Methanol

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

Safety

Toxicity

LD50 in female mice (mg/kg): 6.7 i.v.; 99 s.c. (Adams, 1972)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

(±)-N-(2,6-dimethylphenyl)-2-(ethylpropylamino)butyramide monohydrochloride Chemical Properties,Usage,Production

Originator

Duranest,Astra,US,1976

Uses

Etidocaine Hydrochloride is a local anesthetic amide used during surgical procedures and during labor in pregnancies.

Definition

ChEBI: Etidocaine hydrochloride is an amino acid amide.

Manufacturing Process

α-(n-Propylamino)-n-butyro-2,6-xylidide(0.243 mol) and freshly distilled diethyl sulfate (1.6 mols were mixed in a flask equipped with reflux condenser, drying tube and stirrer. The mixture was stirred for 5 hours at 90°C. After cooling, water (110 ml) was added with stirring for 15 minutes followed by 4M HCl (110 ml). The solution was washed with ether (3 X 100 ml) and made alkaline with 7M NaOH to pH 10-11. The freed base was taken up in ether (3 X 100 ml); the extracts were dried over sodium sulfate, filtered and evaporated. The residue was dissolved in absolute ether (200 ml) and the hydrochloride prepared by addition of ethereal hydrogen chloride. The precipitate was filtered, washed with ether, and recrystallized twice from absolute ethanol/ether and from isopropanol/isopropylether; MP 203°C to 203.5°C; yield: 0.126 mol (52%). The starting material is prepared by reacting 2-bromobutyric acid with sulfonyl chloride to give the acid chloride. It is then reacted with 2,6-xylidine, then with potassium iodide followed by n-propylamine.

Therapeutic Function

Local anesthetic

Biological Functions

Etidocaine hydrochloride (Duranest), although chemically similar to lidocaine, has a more prolonged action. It is used for regional blocks, including epidural anesthesia. It exhibits a preference for motor rather than sensory block; therefore, its use in obstetrics is limited, although fetal drug concentrations remain low. It can be used with or without epinephrine.