18010-40-7 Usage
Description
Bupivacaine hydrochloride is a racemate composed of equimolar amounts of dextrobupivacaine hydrochloride and levobupivacaine hydrochloride, commonly used in its monohydrate form as a local anesthetic. It functions as a Na+ channel blocker, playing a crucial role in the temporary interruption of nerve impulse transmission.
Uses
Used in Medical Applications:
Bupivacaine hydrochloride is used as a local anesthetic for various medical procedures, providing pain relief by blocking the conduction of nerve impulses along nerve fibers. This is particularly useful in surgeries, dental procedures, and other clinical interventions where localized pain control is required.
Additionally, as a Na+ channel blocker, bupivacaine hydrochloride is utilized to regulate the flow of sodium ions across cell membranes, which is essential in stabilizing the electrical potential of nerve and muscle cells, thereby contributing to the overall management of pain and other related conditions.
Originator
Carbostesin,Astra,W. Germany,1967
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 18010-40-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,0,1 and 0 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 18010-40:
(7*1)+(6*8)+(5*0)+(4*1)+(3*0)+(2*4)+(1*0)=67
67 % 10 = 7
So 18010-40-7 is a valid CAS Registry Number.
InChI:InChI=1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H
18010-40-7Relevant articles and documents
Preparation method of levobupivacaine hydrochloride
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, (2017/07/19)
The invention belongs to the technical field of chemical synthesis and in particular relates to a preparation method of levobupivacaine hydrochloride. The preparation method takes racemic or S-configuration 2-piperidinecarboxylic acid as a starting raw material and comprises the following steps: taking the starting raw material and n-butylaldehyde to react and carrying out borohydride reduction reaction to obtain 1-butylpiperidine-2-carboxylic acid; taking the 1-butylpiperidine-2-carboxylic acid and 2,6-dimethylaniline to be subjected to condensation reaction, so as to generate bupivacaine or levobupivacaine; carrying out subsequent treatment to obtain a final product levobupivacaine hydrochloride. Compared with an existing synthesis route, the preparation method has the advantages of short synthesis route, simple method, convenience for operation, low cost and easiness for industrial production; reaction conditions of each step are relatively moderate, a process is stable, a strong-corrosion chlorination reagent is not used, the pollution to environment is reduced and the like.
Preparation process of bupivacaine hydrochloride
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Paragraph 0024; 0025; 0026; 0027, (2017/07/20)
The invention discloses a preparation process of bupivacaine hydrochloride. According to the specific scheme, N-(2,6-xylyl)-2-piperidine formamide is adopted as a starting raw material and dissolved in methylbenzene, then a deacidification agent, a phase transfer catalyst and bromobutane are added, certain temperature is kept for reacting, and after the reaction is finished, filtering is carried out at room temperature, and a bupivacaine solution is obtained; the bupivacaine solution is acidized with an acidification agent, aftertreatment is carried out, and bupivacaine hydrochloride is obtained through drying. According to the preparation process, the solvent can be recycled, the production cost can be reduced, environmental pollution can be reduced, meanwhile, byproducts of other products of the company are fully utilized, refuse reclamation is achieved, and generated waste gas, waste water and industrial residues are reduced.
PROCESS FOR ENANTIOMERIC ENRICHMENT OF 2 ', 6 ' - PIPECOLOXYLIDIDE
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Page/Page column 18-19, (2014/02/15)
The invention discloses a process for enantiomeric enrichment of 2',6'-pipecoloxylidide using a chiral carbamoyl benzoic acid to provide (S)-enantiomer in high yield and high enantiomeric purity. The invention also discloses novel intermediates formed in the process of enantiomeric enrichment of 2',6'-pipecoloxylidide, preparation of N- substituted amidic acids and alkylation of 2',6'-pipecoloxylidide.
