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SML1092 Sigma-Aldrich

Levobupivacaine hydrochloride

≥98% (HPLC)

Synonym: (S)-bupivacaine hydrochloride, (S)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride

  • CAS Number 27262-48-2

  • Empirical Formula (Hill Notation) C18H28N2O · HCl

  • Molecular Weight 324.89

  •  MDL number MFCD01704265

  •  PubChem Substance ID 329825469

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Ion Channels,
Quality Level   100
assay   ≥98% (HPLC)
form   powder
optical activity   [α]/D -10 to -14°, c = 1.0 in H2O
storage condition   desiccated
color   white to beige
solubility   H2O: 20 mg/mL, clear
storage temp.   2-8°C
SMILES string   CC1=C(NC([C@H]2N(CCCC)CCCC2)=O)C(C)=CC=C1.Cl
InChI   1S/C18H28N2O.ClH/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);1H/t16-;/m0./s1
InChI key   SIEYLFHKZGLBNX-NTISSMGPSA-N
Gene Information   human ... SCN4A(6329)

Description

General description

Levobupivacaine belongs to the N-alkyl substituted pipecoloxylidide family and comprises amino-amide group.

Application

Levobupivacaine hydrochloride has been used as an analyte in tandem mass spectrometry. It may be used to test its inhibitory effect on phosphorylation of extracellular signal-regulated kinase (ERK) mediated by capsaicin It may also be used as a component of poly(D,L-lactide-co-glycolide) (PLGA) microparticles for testing its sustainable release by electrospraying technique

Packaging

10, 50 mg in glass bottle

Biochem/physiol Actions

Levobupivacaine hydrochloride is a sodium channel blocker used as a long-acting local anaesthetic for epidural anesthesia. Levobupivacaine is the (S)-isomer of bupivacaine, with efficacy similar to that of bupivacaine with a reduced risk of cardiotoxicity.

Levobupivacaine mediates its action by blocking the action potential and sodium passage in neuronal membrane.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Ion Channels Research

Ion transport across the relatively impermeable lipid bilayer of the cell membrane is accomplished via membrane proteins known as ion channels, pumps and transporters. Ion channels are gated pores an...
Keywords: Biological processes, Cell signaling, Diseases, Hormones, Ligands, Neurotransmitters

Peer-Reviewed Papers
15

References

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