Bupivacaine hydrochloride

Base Information

• Chemical Name: Bupivacaine hydrochloride
• CAS No.: 18010-40-7
• Deprecated CAS: 14252-80-3
• Molecular Formula: C₁₈H₂₈N₂O*ClH
• Molecular Weight: 324.894
• European Community (EC) Number: 241-917-8,627-065-3
• NSC Number: 758631,119660
• UNII: AKA908P8J1
• DSSTox Substance ID: DTXSID0030877
• Wikidata: Q27888209
• NCI Thesaurus Code: C28876
• RXCUI: 1375412
• Pharos Ligand ID: 1K8VL4VQM52G
• ChEMBL ID: CHEMBL1200396
• Mol file: 18010-40-7.mol

Synonyms:1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide;Bupivacain Janapharm;Bupivacain RPR;Bupivacain-RPR;Bupivacaina Braun;Bupivacaine;Bupivacaine Anhydrous;Bupivacaine Carbonate;Bupivacaine Hydrochloride;Bupivacaine Monohydrochloride, Monohydrate;Buvacaina;Carbostesin;Dolanaest;Marcain;Marcaine;Sensorcaine;Svedocain Sin Vasoconstr

Chemical Property of Bupivacaine hydrochloride

Chemical Property:

• Vapor Pressure: 2.24E-07mmHg at 25°C
• Melting Point: 257°C(dec.)(lit.)
• Boiling Point: 423.4 °C at 760 mmHg
• Flash Point: 209.9 °C
• PSA: 32.34000
• LogP: 4.70940
• Solubility.: ≥10.25 mg/mL in DMSO; ≥16.23 mg/mL in H2O with ultrasonic; ≥69.2 mg/mL in EtOH
• Water Solubility.: Soluble in water
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 324.1968412
• Heavy Atom Count: 22
• Complexity: 321

Purity/Quality:

98% ^*data from raw suppliers

Bupivacaine hydrochloride ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
• Recent ClinicalTrials: Comparing Liposomal Bupivacaine Versus Standard Bupivacaine in Colorectal Surgery
• Recent EU Clinical Trials: Pharmacodynamics of Liposomal Bupivacaine for Peripheral Nerve Blockade: A Randomized, Triple-blinded, Cross Over Study in Volunteers
• Recent NIPH Clinical Trials: Study of pain control on Impacted Mandibular Third Molar
• Uses: Local anesthesic;Na+ channel blocker
• Therapeutic Function: Local anesthetic

Technology Process of Bupivacaine hydrochloride

There total 6 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: 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: 92.0%

→ bupivacaine hydrochloride (14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In water; toluene; at 80 - 85 ℃; for 8.5h;

With hydrogenchloride; In isopropyl alcohol; acetone; toluene; at 40 ℃;

Reference yield:

pipecolic Acid (4043-87-2,83680-83-5) → bupivacaine hydrochloride (14252-80-3,15233-43-9,18010-40-7,27262-46-0,27262-48-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / water / 12 h / 20 °C

2.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 1 h / 20 °C

2.2: 18 h / 20 °C

3.1: palladium on activated charcoal; hydrogen / methanol / 0.5 h / 50 °C / Autoclave

4.1: N,N-dimethyl-formamide / 12 h / 20 - 80 °C

4.2: 20 °C

With palladium on activated charcoal; hydrogen; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; sodium hydroxide; In methanol; water; N,N-dimethyl-formamide;

upstream raw materials:

pipecolic Acid

N-benzyloxycarbonyl D/L-pipecolinic acid

1-bromo-butane

2',6'-pipecoloxylidide

Downstream raw materials:

(+)-Bupivacaine

levobupivacaine

C₁₈H₂₈N₂O*C₄₂H₇₀O₃₅*ClH

racemic bupivacaine

Refernces

• 1、 -. "Preparation method of bupivacaine hydrochloride". . . Retrieved 2018/01/12.
• 2、 -. "Preparation process of bupivacaine hydrochloride". Paragraph 0024; 0025; 0026; 0027. . Retrieved 2017/07/20.