Bupivacaine Hydrochloride

Names

[ Name ]:
Bupivacaine Hydrochloride

[Synonym ]:
Win 11,318
Bupivacaine HCl H2-O
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrate hydrochloride
Bupivacaine hydrochloride
Marcaine (TN)
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide,hydrate,hydrochloride
2-Piperidinecarboxamide,1-butyl-N-(2,6-dimethylphenyl)-,monohydrochloride,monohydrate

Biological Activity

[Description]:

Bupivacaine hydrochloride monohydrate is a NMDA receptor inhibitor. Bupivacaine hydrochloride monohydrate can block sodium, L-calcium, and potassium channels. Bupivacaine hydrochloride monohydrate potently blocks SCN5A channels with the IC50 of 69.5 μM. Bupivacaine hydrochloride monohydrate can be used for the research of chronic pain[1][2][3].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> iGluR

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Signaling Pathways >> Membrane Transporter/Ion Channel >> Calcium Channel

Research Areas >> Cancer

Research Areas >> Neurological Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

Signaling Pathways >> Membrane Transporter/Ion Channel >> iGluR

[Target]

NMDA Receptor

[References]

[1]. Meaghan A Paganelli, et al. Actions of Bupivacaine, a widely used local anesthetic, on NMDA receptor responses. J Neurosci. 2015 Jan 14;35(2):831-42.

[2]. Alexander P Schwoerer, et al. A Comparative Analysis of Bupivacaine and Ropivacaine Effects on Human Cardiac SCN5A Channels. Anesth Analg. 2015 Jun;120(6):1226-34.

[3]. Carsten Stoetzer, et al. Inhibition of Voltage-Gated Na⁺ Channels by Bupivacaine Is Enhanced by the Adjuvants Buprenorphine, Ketamine, and Clonidine. Reg Anesth Pain Med.Jul/Aug 2017;42(4):462-468.

Chemical & Physical Properties

[ Melting Point ]:
255-259℃

[ Molecular Formula ]:
C₁₈H₃₁ClN₂O₂

[ Molecular Weight ]:
342.90

[ Exact Mass ]:
342.20700

[ PSA ]:
45.06000

[ LogP ]:
5.22160

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300 + H310 + H330

[ Precautionary Statements ]:
P260-P264-P280-P284-P301 + P310-P302 + P350

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
26/27/28

[ Safety Phrases ]:
22-36/37/39-45

[ RIDADR ]:
UN 2811 6.1 / PGII

[ RTECS ]:
TK6125000

[ Hazard Class ]:
6.1

Articles

Differential requirement for IL-2 and IL-15 during bifurcated development of thymic regulatory T cells.

J. Immunol. 193(11) , 5525-33, (2014)

The developmental pathways of regulatory T cells (T(reg)) generation in the thymus are not fully understood. In this study, we reconstituted thymic development of Zap70-deficient thymocytes with a tet...

The distinct effects of lipid emulsions used for "lipid resuscitation" on gating and bupivacaine-induced inhibition of the cardiac sodium channel Nav1.5.

Anesth. Analg. 117(5) , 1101-8, (2013)

Systemic administration of lipid emulsions is an established treatment for local anesthetic intoxication. However, it is unclear by which mechanisms lipids achieve this function. The high cardiac toxi...

MK-801-induced behavioural sensitisation alters dopamine release and turnover in rat prefrontal cortex.

Psychopharmacol. Ser. 232(3) , 509-17, (2015)

Repeated exposure to psychostimulants that either increase dopamine (DA) release or target N-methyl-D-aspartate (NMDA) receptors can induce behavioural sensitisation, a phenomenon that may be importan...