bupivacaine hydrochloride Chemical Properties

Melting point:

257°C(dec.)(lit.)

storage temp. 

4°C, protect from light

Water Solubility 

Soluble in water

solubility 

≥10.25 mg/mL in DMSO; ≥16.23 mg/mL in H2O with ultrasonic; ≥69.2 mg/mL in EtOH

form 

Solid

color 

White to Almost white

Stability:

Hygroscopic

Safety Information

Hazard Codes 

T+

Risk Statements 

26/27/28

Safety Statements 

22-36/37/39-45

RIDADR 

UN 2811 6.1/PG 2

RTECS 

TK6125000

HS Code 

2933.39.9200

HazardClass 

6.1

PackingGroup 

II

Toxicity

LD50 oral in rabbit: 18mg/kg

bupivacaine hydrochloride Usage And Synthesis

Originator

Carbostesin,Astra,W. Germany,1967

Uses

Local anesthesic;Na+ channel blocker

Definition

ChEBI: A racemate composed of equimolar amounts of dextrobupivacaine hydrochloride and levobupivacaine hydrochloride. The monohydrate form is commonly used as a local anaesthetic.

Manufacturing Process

121 parts by weight of 2.6-xylidine are heated with 400 parts of diethylmalonate at 160°C for 1 hour, and the alcohol formed by the reaction is allowed to distill off. Thereafter the reaction mass is cooled to 80°C, and 500 parts of alcohol are added. After cooling the dixylidide is sucked off, and the alcohol solution with malonic ester monoxylidide is poured into 2,000 parts of water. The monoxylidide precipitates, is filtered off and washed with water, and recrystallized in diluted alcohol. Nitrosation thereafter takes place by dissolving the dried monoxylidide in chloroform and by introducing nitrosyl chloride at 0°C until the nitrosation is completed. The isonitrosomalonic ester xylidide is filtered off and dried. Thereafter the reduction takes place with zinc powder and formic acid at 90°-100°C.
The formic acid is distilled off, and the remainder dissolved in warm benzene and washed with a bicarbonate solution to a neutral reaction. After the benzene has been distilled off, the aminomalonic ester xylidide is obtained. This is treated with an equal quantity of sodium ethylate and boiled with twice the theoretical quantity of tetramethylene bromide in absolute alcohol. After 6 hours of boiling, the sodium bromide formed is separated, and the mixture is steamdistilled in order to remove the excess of tetramethylene bromide. The remaining oil, which mainly consists of deltabromobutylaminomalonic ester xylidide is separated from the water and boiled with 3 parts of concentrated hydrochloric acid for 3 hours. Thereafter carbonfiltering and evaporation to dryness under vacuum takes place. The residue is dissolved in water, and the pH adjusted with sodium hydroxide to 5.5. The solution is extracted twice with ether, and the water is made strongly alkaline with sodium hydroxide.
The oil precipitates and is crystallized after a time. The crystals are separated and dried under vacuum. The pipecolyl-2,6-xylidide produced is alkylated by boiling for 10-20 hours with 0.6 part n-butylbromide in an n-butanol solution in the presence of 0.5 part potassium carbonate. The potassium carbonate is filtered off and the butanol is distilled off in vacuum. The residue is dissolved in diluted hydrochloric acid and carbon treated, after which the base is precipitated with sodium hydroxide in the form of white crystals, which are filtered off and washed with water. The base obtained, which consists of N-n-butyl-pipecolyl-2,6-xylidide is sufficiently pure for the production of salts.

brand name

Marcaine (Hospira); Sensorcaine (AstraZeneca).

Therapeutic Function

Local anesthetic

Biological Activity

bupivacaine hydrochloride is a local anaesthetic drug belonging to the amino amide group.bupivacaine hydrochloride is an effective local anesthetic agent. it has a rapid onset time, a high frequency of surgical anesthesia, a long duration, and a low incid

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