LKT Labs

Biochemicals for Life Science Research

Bupivacaine

Bupivacaine

Product ID B8261
Cas No. 38396-39-3
Purity ≥99%
Product Unit SizeCostQuantityStock
1 g $75.00 In stock
5 g $187.00 In stock
25 g $386.00 In stock
Bulk Quote

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Description

Bupivacaine is an amino amide anesthetic that decreases current amplitude and inhibits whole cell K+ currents in Ca2+-activated (BK/SK) K+ channels and N-type voltage-gated (Kv1/shaker and Kv3 KCNA/KCNC) K+ channels. Bupivacaine also inhibits voltage-gated Na+ channels and tandem pore domain (TASK-2/KCNK-5) K+ channels. Bupivacaine may be neurotoxic at high doses, activating p38 MAPK, increasing levels of ROS and WDR53, and inducing apoptosis in neuroblastoma cells. In other cellular models, bupivacaine induces depolarization of the mitochondrial membrane potential, resulting in apoptosis.

Product Info

Cas No.

38396-39-3
Purity

≥99%
Formula

C18H28N2O
Formula Wt.

288.43
Chemical Name

1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
IUPAC Name

1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Melting Point

107-108°C
Solubility

DMF (30 mg/mL), DMSO (50 mg/mL) Ethanol (50mg/mL) Water: Insoluble
Appearance

White to off white powder

Shipping and Storage

Store Temp

Ambient
Ship Temp

Ambient

Downloads

MSDS

B8261 MSDS PDF
Info Sheet

B8261 Info Sheet PDF

References

Harato M, Huang L, Kondo F, et al. Bupivacaine-induced apoptosis independently of WDR35 expression in mouse neuroblastoma Neuro2a cells. BMC Neurosci. 2012 Dec 10;13:149. PMID: 23227925.

Martín P, Enrique N, Palomo AR, et al. Bupivacaine inhibits large conductance, voltage- and Ca2+- activated K+ channels in human umbilical artery smooth muscle cells. Channels (Austin). 2012 May-Jun;6(3):174-80. PMID: 22688134.

Lu J, Xu SY, Zhang QG, et al. Bupivacaine induces apoptosis via mitochondria and p38 MAPK dependent pathways. Eur J Pharmacol. 2011 Apr 25;657(1-3):51-8. PMID: 21315711.

Cela O, Piccoli C, Scrima R, et al. Bupivacaine uncouples the mitochondrial oxidative phosphorylation, inhibits respiratory chain complexes I and III and enhances ROS production: results of a study on cell cultures. Mitochondrion. 2010 Aug;10(5):487-96. PMID: 20546950.

Nilsson J, Madeja M, Elinder F, et al. Bupivacaine blocks N-type inactivating Kv channels in the open state: no allosteric effect on inactivation kinetics. Biophys J. 2008 Dec;95(11):5138-52. PMID: 18790854.

Kindler CH, Paul M, Zou H, et al. Amide local anesthetics potently inhibit the human tandem pore domain background K+ channel TASK-2 (KCNK5). J Pharmacol Exp Ther. 2003 Jul;306(1):84-92. PMID: 12660311.

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