Bupivacaine

Base Information

• Chemical Name: Bupivacaine
• CAS No.: 38396-39-3
• Deprecated CAS: 2180-92-9
• Molecular Formula: C₁₈H₂₈N₂O
• Molecular Weight: 288.433
• European Community (EC) Number: 218-553-3,253-911-2
• UNII: Y8335394RO
• DSSTox Substance ID: DTXSID2022703
• Nikkaji Number: J7.351B
• Wikipedia: Bupivacaine
• Wikidata: Q422806
• NCI Thesaurus Code: C62011
• RXCUI: 1815
• Pharos Ligand ID: 1K8VL4VQM52G
• Metabolomics Workbench ID: 143582
• ChEMBL ID: CHEMBL1098
• Mol file: 38396-39-3.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

Chemical Property:

• Melting Point: 106-110℃
• Boiling Point: 423.4 °C at 760 mmHg
• PKA: 14.85±0.70(Predicted)
• Flash Point: 209.9 °C
• PSA: 35.83000
• Density: 1.032 g/cm³
• LogP: 4.48390
• Water Solubility.: Soluble in water, ethanol, chloroform (slightly ), and acetone (slightly ).
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 288.220163521
• Heavy Atom Count: 21
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

Bupivacaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
• Recent ClinicalTrials: Effects of Stellate Ganglion Block in Post-traumatic Stress Disorder
• Recent EU Clinical Trials: ECOGUIDED GENICULAR NERVE BLOCK IN PATIENTS WITH KNEE OSTEOARTHRITIS BY LOCAL ANESTHETIC OR BY COMBINATION OF LOCAL ANESTHETIC AND CORTICOID: PLACEBO-CONTROLLED RANDOMIZED BLIND CLINICAL TRIAL
• Recent NIPH Clinical Trials: Comparision of Anesthetic drug combinations Bupivacaine with clonidine and Levobupivacaine with clonidine used in nerve blocks for surgeries of upper limb
• Description: Bupivacaine is a sodium channel blocker and local anesthetic. It inhibits sodium currents in rat dorsal horn neurons in a concentration-dependent manner and inhibits synaptic transmission in rat sympathetic ganglia, increasing the firing threshold when used at a concentration of 200 nM. Bupivacaine (10 μM) blocks cardiac sodium channels in a use-dependent manner and inhibits respiration in cardiac cell mitochondria when palmitoyl-carnitine or acetyl-carnitine are used as substrates (IC50s = 0.78 and 0.37 mM, respectively). It also reduces thermal hyperplasia in a rat model of sciatic ligation injury when 0.6 ml of a 0.5% solution is administered into the perinerve space, and the duration of this effect is extended by co-administration of the NMDA receptor antagonist MK-801 . Formulations containing bupivacaine have been used as local anesthetics for surgery, oral surgery, and dental procedures and for anesthetic purposes in research studies using animals.
• Uses: Bupivacaine acts as a potent and long-acting local anesthetic agent in vivo. At 100 μM, it has been reported to inhibit the uptake of dopamine in striatal synaptosomes by 47%.

Technology Process of Bupivacaine

There total 10 articles about Bupivacaine 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: 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;

Reference yield: 89.0%

2-pyridine-carboxamide-N-(2,6-dimethylphenyl) (39627-98-0) + butyraldehyde (123-72-8) → racemic bupivacaine (14252-80-3,2180-92-9,27262-45-9,27262-47-1,38396-39-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 50 ℃;

DOI:10.1002/ejoc.201700824

upstream raw materials:

1-bromo-butane

bupivacaine hydrochloride

(+)-Bupivacaine

racemic 1-butylpiperidine-2-carboxylic acid

Refernces

• 1、 -. "Preparation method of levobupivacaine hydrochloride". Paragraph 0053; 0054. . Retrieved 2017/09/26.
• 2、 Suveges, Nícolas S.,de Souza, Rodrigo O. M. A.,Gutmann, Bernhard,Kappe, C. Oliver. "Synthesis of Mepivacaine and Its Analogues by a Continuous-Flow Tandem Hydrogenation/Reductive Amination Strategy". . p. 6511 - 6517. Retrieved 2017/12/02.