Levobupivacaine

Base Information

• Chemical Name: Levobupivacaine
• CAS No.: 27262-47-1
• Molecular Formula: C18H28N2O
• Molecular Weight: 288.433
• Hs Code.: 2933399090
• European Community (EC) Number: 690-076-7
• UNII: A5H73K9U3W
• DSSTox Substance ID: DTXSID8048496
• Nikkaji Number: J153.469F
• Wikipedia: Levobupivacaine
• Wikidata: Q3272027
• NCI Thesaurus Code: C87594
• Pharos Ligand ID: 1K8VDFWQQMK8
• Metabolomics Workbench ID: 43248
• ChEMBL ID: CHEMBL1201193
• Mol file: 27262-47-1.mol

Synonyms:Chirocaine;levobupivacaine;levobupivacaine hydrochloride

Chemical Property of Levobupivacaine

Chemical Property:

• Melting Point: 254ºC (dec.)(lit.)
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 423.4 °C at 760 mmHg
• PKA: 14.85±0.70(Predicted)
• Flash Point: 209.9 °C
• PSA: 32.34000
• Density: 1.032 g/cm³
• LogP: 4.70940
• Storage Temp.: Refrigerator
• 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

(S)-(-)-Bupivacaine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T+
• Hazard Codes: Xn,T+

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C
• Isomeric SMILES: CCCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C
• Recent ClinicalTrials: Safety and Efficacy of Magnesium Sulphate as an Adjuvant to Levobupivacaine in Ultra-sound Guided Transversus Abdominis Plan Block in Pediatric Abdominal Cancer Surgery
• Recent EU Clinical Trials: PAIN CONTROL WITH THE USE OF WALANT IN TOTAL TRAPEZECTOMY. RANDOMIZED CLINICAL TRIAL
• Recent NIPH Clinical Trials: The analgesic efficacy of constant fentanyl infusion and IV acetaminophen with transversus abdominis plane block in thoracoscopic esophagectomy: a randomized controlled trial.
• Uses: Local anaesthetic used for epidural and intrathecal anaesthesia.
• Therapeutic Function: Local anesthetic

Technology Process of Levobupivacaine

There total 41 articles about Levobupivacaine 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: 95.0%

1-bromo-butane (109-65-9) + (S)-2',6'-pipecoloxylidide (27262-40-4) → levobupivacaine (27262-47-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 3h;

Reference yield: 94.8%

chloroform (67-66-3,8013-54-5) + C9H18ClN + 2,6-dimethylaniline (87-62-7) → levobupivacaine (27262-47-1)

Guidance literature:

With [2,2]bipyridinyl; cesiumhydroxide monohydrate; copper diacetate; potassium carbonate; In toluene; at 100 - 105 ℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;

upstream raw materials:

1-bromo-butane

bupivacaine hydrochloride

(+)-Bupivacaine

racemic 1-butylpiperidine-2-carboxylic acid

Downstream raw materials:

(+)-Bupivacaine

Refernces

• 1、 Yang, Yuyan,Li, Hua,You, Zhonglin,Zhang, Xingxian. "A convenient and highly enantioselective synthesis of (S)-2-pipecolic acid: an efficient access to caine anesthetics". . p. 3084 - 3089. Retrieved 2021/08/12.
• 2、 -. "Insoluble complex, pharmaceutical composition and application of pharmaceutical composition". Paragraph 0081-0082. . Retrieved 2020/04/17.