Bupivacaine hydrochloride

Base Information

• Chemical Name: Bupivacaine hydrochloride
• CAS No.: 14252-80-3
• Molecular Formula: C18H28N2O.ClH
• Molecular Weight: 324.88900
• Hs Code.: 2933399090
• Mol file: 14252-80-3.mol

Synonyms:Bupivacaine hydrochloride;

Chemical Property of Bupivacaine hydrochloride

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 2.24E-07mmHg at 25°C
• Melting Point: 249-251oC
• Boiling Point: 423.4oC at 760 mmHg
• Flash Point: 209.9oC
• PSA: 32.34000
• LogP: 4.70940
• Storage Temp.: Refrigerator
• Solubility.: Soluble in water, freely soluble in alcohol.

Purity/Quality:

99%min. ^*data from raw suppliers

Bupivacaine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R26/27/28:
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Uses: antineoplastic Sodium channel blocker, local anesthetic Bupivacaine Hydrochloride is the salt form of Bupivacaine (B689561); is a sodium channel blocker, local anesthetic.
• Biological Functions: Bupivacaine hydrochloride (Marcaine, Sensorcaine) has particularly long action, and some nerve blocks last more than 24 hours; this is often an advantage for postoperative analgesia. Its use for epidural anesthesia in obstetrics has attracted interest because it can relieve the pain of labor at concentrations as low as 0.125% while permitting some motor activity of abdominal muscles to aid in expelling the fetus. The lower concentration minimizes the possibility of cardiac toxicity. Fetal drug concentrations remain low, and drug-induced neurobehavioral changes are not observed in the newborn. Bupivacaine also is approved for spinal anesthesia and is approximately four times more potent and more toxic than mepivacaine and lidocaine. It can be used with or without epinephrine.

Technology Process of Bupivacaine hydrochloride

There total 16 articles about Bupivacaine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(+)-Bupivacaine (27262-45-9) → racemic bupivacaine (14252-80-3,2180-92-9,27262-45-9,27262-47-1,38396-39-3)

Guidance literature:

With water; In ethylene glycol; at 138 ℃; for 9h;

Reference yield: 96.0%

1-bromo-butane (109-65-9) + 2',6'-pipecoloxylidide (15883-20-2,27262-40-4,27262-43-7,78341-12-5) → bupivacaine hydrochloride (14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2)

Guidance literature:

1-bromo-butane; 2',6'-pipecoloxylidide; With tetrabutylammomium bromide; potassium carbonate; In toluene; at 80 - 85 ℃; for 5h; Green chemistry;

With hydrogenchloride; In water; toluene; Reagent/catalyst; Green chemistry;

Reference yield: 93.0%

bupivacaine hydrochloride (14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2) → racemic bupivacaine (14252-80-3,2180-92-9,27262-45-9,27262-47-1,38396-39-3)

Guidance literature:

With sodium hydroxide; In water; pH=9.5;

upstream raw materials:

1-bromo-butane

bupivacaine hydrochloride

(+)-Bupivacaine

racemic 1-butylpiperidine-2-carboxylic acid

Downstream raw materials:

racemic bupivacaine

(+)-Bupivacaine

levobupivacaine

Refernces

• 1、 -. "HYDROPHOBIC ACID ADDITION SALTS AND PHARMACEUTICAL FORMULATIONS THEREOF". Page/Page column 86. . Retrieved 2019/05/22.
• 2、 -. "Preparation method of levobupivacaine hydrochloride". Paragraph 0054; 0055. . Retrieved 2017/07/19.