27262-45-9

Basic information

• Product Name: (R)-(+)-BUPIVACAINE HCL
• Synonyms: D-(+)-Bupivacaine;d-Bupivacaine;(2R)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2β-carboxamide;(R)-(+)-BUPIVACAINE HCL;1-butyl-6’-pipecoloxylididd-(+)-2;(R)-(+)-Bupivacaine;2',6'-Pipecoloxylidide, 1-butyl-, (+)- (8CI);2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, (2R)-
• CAS NO: 27262-45-9
• Molecular Formula: C₁₈H₂₈N₂O
• Molecular Weight: 288.43
• Product Categories: Chiral Standards
• Mol File: 27262-45-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 430.65°C (rough estimate)
• Flash Point: 209.9ºC
• Appearance: /
• Density: 1.0238 (rough estimate)
• Vapor Pressure: 2.24E-07mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• CAS DataBase Reference: (R)-(+)-BUPIVACAINE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-BUPIVACAINE HCL(27262-45-9)
• EPA Substance Registry System: (R)-(+)-BUPIVACAINE HCL(27262-45-9)

Safety Data

• Hazardous Substances Data: 27262-45-9(Hazardous Substances Data)

Usage

Description

(R)-(+)-BUPIVACAINE HCL, also known as the (R)-(+)-enantiomer of bupivacaine, is a chiral local anesthetic drug. It possesses a unique molecular structure that allows it to selectively block nerve conduction, providing pain relief during medical procedures. Its hydrochloride salt form enhances its solubility and stability, making it suitable for various applications in the medical field.

Uses

Used in Medical Applications:
(R)-(+)-BUPIVACAINE HCL is used as a local anesthetic for providing pain relief during surgical procedures and other medical interventions. It is particularly effective for epidural and intrathecal anesthesia, where it can be administered near the spinal cord to numb a specific region of the body, reducing the need for general anesthesia and its associated risks.
Used in Pain Management:
(R)-(+)-BUPIVACAINE HCL is also used for managing postoperative pain and other types of chronic pain. Its long-lasting anesthetic effect makes it a valuable option for patients who require extended periods of pain relief without the need for continuous administration.
Used in Obstetrics:
In the field of obstetrics, (R)-(+)-BUPIVACAINE HCL is used for providing pain relief during labor and delivery. It can be administered via an epidural injection, which helps to reduce the pain associated with contractions and childbirth, allowing for a more comfortable and controlled experience for the mother.
Used in Regional Anesthesia:
(R)-(+)-BUPIVACAINE HCL is employed in regional anesthesia for various surgeries, including orthopedic, vascular, and urological procedures. Its ability to block nerve conduction in a specific area makes it an ideal choice for surgeries that require localized pain relief without affecting the patient's consciousness or overall bodily function.

InChI:InChI=1/C18H28N2O/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)/t16-/m1/s1

Upstream product

• 109-65-9 1-bromo-butane 
• 14252-80-3 bupivacaine hydrochloride 
• 856838-98-7 racemic 1-butylpiperidine-2-carboxylic acid 
• 87-62-7 2,6-dimethylaniline 
• 4043-87-2 pipecolic Acid 
• 39627-98-0 2-pyridine-carboxamide-N-(2,6-dimethylphenyl) 
• 123-72-8 butyraldehyde 
• 98-98-6 2-Picolinic acid 
• 14252-80-3 racemic bupivacaine 
• 27262-40-4 (S)-2',6'-pipecoloxylidide 

Downstream Products

• 27262-47-1 levobupivacaine 
• 14252-80-3 racemic bupivacaine 

Relevant articles and documents

Enantioseparation of racemic bupivacaine via ultrasonic-assisted diastereomeric crystallization using 12,14-dinitrodehydroabietic acid

12,14-Dinitrodehydroabietic acid (12,14-dinitroDHAA), a chiral acid obtained by the nitration of optical dehydroabietic acid (DHAA), was successfully employed as resolving agent. The resolution of racemic bupivacaine by ultrasonic-assisted diastereomeric crystallization in ethanol was investigated. The results indicated that ultrasonic-assist can well facilitate resolution of (R,S)-bupivacaine and a higher enantiomeric excess (ee) and yield was obtained for (S)-bupivacaine, and while without ultrasound, the ee value decreases by increasing the crystallization time. A Box-Behnken experimental design with four factors (amount of 12,14-dinitroDHAA, ethanol amount, ultrasonic power and crystallization temperature) combined with response surface methodology (RSM) was applied to explore resolution effects. A second-order polynomial equation was adequate to model the relationship between the ee (or yield) and the dependent variables. When maintaining a lower limit of 90% for the yield of (S)-bupivacaine, the optimal resolution conditions by RSM were 12,14-dinitroDHAA/bupivacaine molar ratio of 1.6, solvent/propranolol ratio of 16.5 mL/g, 63.2 W ultrasonic power and crystallization temperature of 0 °C, respectively. Under the optimal conditions, the experimental ee and yield of (S)-bupivacaine were 69.8% and 87.5%.

Synthesis of Mepivacaine and Its Analogues by a Continuous-Flow Tandem Hydrogenation/Reductive Amination Strategy

Herein we report a convenient, fast, and high-yielding method for the generation of the racemic amide anaesthetics mepivacaine, ropivacaine, and bupivacaine. Coupling of α-picolinic acid and 2,6-xylidine under sealed-vessel microwave conditions generates the intermediate amide after a reaction time of only 5 min at 150 °C. Subsequent reaction in a continuous-flow high-pressure hydrogenator (H-Cube ProTM) in the presence of the respective aldehyde directly converts the intermediate to the final amide anaesthetics in a continuous, integrated, multi-step ring-hydrogenation/reductive amination protocol. Merits and limitations of the protocol are discussed.

Preparation method of levobupivacaine hydrochloride

The invention belongs to the technical field of chemical synthesis and particularly relates to a preparation method of levobupivacaine hydrochloride. The preparation method comprises the steps of carrying out catalytic hydrogenation on racemic or S-form 2-piperidinecarboxylicacid as a raw material and n-butanal so as to obtain 1-butylpiperidine-2-carboxylic acid, carrying out condensation reaction on 1-butylpiperidine-2-carboxylic acid and 2,6-dimethylaniline so as to generate bupivacaine or levobupivacaine, and carrying out subsequent treatment, so as to obtain a final product, namely levobupivacaine hydrochloride. Compared with existing synthetic routes, the preparation method has the advantages that the synthetic route is short, the method is simple, convenient in operation, low in cost and easy for industrial production, reaction conditions of each step are relatively mild, the process is stable, a strong-corrosion chlorinated reagent is not used, and the environmental pollution is reduced.