Skip to Content
Merck
All Photos(1)

Documents

SML1092

Sigma-Aldrich

Levobupivacaine hydrochloride

≥98% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C18H28N2O · HCl
CAS Number:
Molecular Weight:
324.89
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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)

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

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Joanne Guay et al.
The Cochrane database of systematic reviews, 3, CD006715-CD006715 (2019-03-02)
General anaesthesia combined with epidural analgesia may have a beneficial effect on clinical outcomes. However, use of epidural analgesia for cardiac surgery is controversial due to a theoretical increased risk of epidural haematoma associated with systemic heparinization. This review was
Different effects of local anesthetics on extracellular signal-regulated kinase phosphorylation in rat dorsal horn neurons
Zhang L, et al.
European Journal of Pharmacology, 734(6), 132-136 (2014)
Salima Qudsi-Sinclair et al.
Pain practice : the official journal of World Institute of Pain, 17(5), 578-588 (2016-09-20)
Knee osteoarthritis is a disease that affects a third of the population over 65 years of age, and it is increasingly becoming a motive for consultation and a source of pain and disability. The gold standard surgical treatment is a total
Lianxi Zhang et al.
European journal of pharmacology, 734, 132-136 (2014-04-15)
Local anesthetics, which are widely known to be neuronal voltage-gated Na(+) channel blockers, also affect a variety of other ion channels, N-methyl-d-asparate (NMDA) receptors and α-amino-3-hydroxy-5-methyl-4-izoxazolepropionic acid (AMPA) receptors. Glutamate, which is released from presynaptic fibers, activates extracellular signal-regulated kinase
Crina L Burlacu et al.
Therapeutics and clinical risk management, 4(2), 381-392 (2008-08-30)
In recent years levobupivacaine, the pure S (-)-enantiomer of bupivacaine, emerged as a safer alternative for regional anesthesia than its racemic parent. It demonstrated less affinity and strength of depressant effects onto myocardial and central nervous vital centers in pharmacodynamic

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service