27262-46-0

Basic information

• Product Name: (R)-(+)-Bupivacaine monohydrochloride
• Synonyms: 2',6'-Pipecoloxylidide, 1-butyl-, monohydrochloride, (+)- (8CI);2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, (2R)-;2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, (R)-;(R)-(+)-Bupivacaine Hydrochloride;1-Butyl-2',6'-pipecoloxylidide Monohydrochloride;(+)-Bupivacaine monohydrochloride;(R)-(+)-Bupivacaine monohydrochloride;dextrobupivacaine hydrochloride (anhydrous)
• CAS NO: 27262-46-0
• Molecular Formula: C₁₈H₂₈N₂O*ClH
• Molecular Weight: 324.94
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals;Chiral Standards
• Mol File: 27262-46-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 258 °C
• Boiling Point: 423.4°Cat760mmHg
• Flash Point: 209.9°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 2.24E-07mmHg at 25°C
• CAS DataBase Reference: (R)-(+)-Bupivacaine monohydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-Bupivacaine monohydrochloride(27262-46-0)
• EPA Substance Registry System: (R)-(+)-Bupivacaine monohydrochloride(27262-46-0)

Safety Data

• Hazardous Substances Data: 27262-46-0(Hazardous Substances Data)

Usage

Description

(R)-(+)-Bupivacaine monohydrochloride, also known as dextrobupivacaine, is a chiral local anesthetic drug derived from the bupivacaine family. It is characterized by its ability to block nerve conduction and provide pain relief through its interaction with the sodium channels in nerve cells. (R)-(+)-Bupivacaine monohydrochloride is the active isomer of bupivacaine, which means it possesses the desired anesthetic properties while minimizing potential side effects.

Uses

Used in Medical Applications:
(R)-(+)-Bupivacaine monohydrochloride is used as a local anesthetic for various medical procedures, including epidural and intrathecal anesthesia. It is particularly effective in providing pain relief during surgeries, labor, and postoperative pain management. The compound's long-lasting anesthetic effect and minimal systemic toxicity make it a preferred choice for these applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (R)-(+)-Bupivacaine monohydrochloride is used as an active ingredient in the formulation of various anesthetic products. These products are designed to target specific medical conditions and procedures, ensuring optimal pain relief and patient comfort during and after medical interventions.
Used in Research and Development:
(R)-(+)-Bupivacaine monohydrochloride is also utilized in research and development for the study of anesthetic mechanisms, drug interactions, and the development of new anesthetic agents. Its unique properties and applications make it a valuable compound for advancing the understanding of local anesthesia and its potential applications in medicine.

InChI:InChI=1/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/t16-;/m1./s1

Upstream product

• 856838-98-7 racemic 1-butylpiperidine-2-carboxylic acid 
• 109-65-9 1-bromo-butane 
• 15883-20-2 2',6'-pipecoloxylidide 
• 28697-07-6 N-benzyloxycarbonyl D/L-pipecolinic acid 
• 4043-87-2 pipecolic Acid 

Downstream Products

• 27262-45-9 (+)-Bupivacaine 
• 27262-47-1 levobupivacaine 
• 774604-08-9 C₁₈H₂₈N₂O*C₄₂H₇₀O₃₅*ClH 
• 14252-80-3 racemic bupivacaine 

Relevant articles and documents

Preparation method of levobupivacaine hydrochloride

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

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

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.