Specifications
- Purity
- ≥98% (T)
- Appearance
- White to off-white powder
- Identity
- 1H-NMR
Properties
- Solvents
- water (10mg/ml), DMSO (20mg/ml), ethanol (20mg/ml), chloroform or acetone (slightly)
Available from stock
Bupivacaine hydrochloride monohydrate
- SKU
- B0326
Category: Metabolites
- Synonyms
- 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide , 1-Butyl-2',6'-pipecoloxylidide
- 73360-54-0
- CAS-Number
- C18H28N2O · HCl · H2O
- Molecular Formula
- 342.9
- Molecular Weight
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
- Shipping
- AMBIENT
- Short Term Storage
- RT
- Long Term Storage
- RT
- Handling Advice
- Protect from light and moisture.
- Use / Stability
- Stable for at least 2 years after receipt when stored at RT.
- Hazard statements
- H300 + H310 + H330
- Precautionary statements
- P260-P264-P280-P284-P301 + P310-P302 + P350
- GHS Symbol
- GHS06
- Signal word
- Danger
- RIDADR
- UN 2811 6.1
- Transportation
- Packing Group II
- Description
- Bupivacaine is an amino amide local anesthetic that decreases current amplitude and inhibits whole cell K+ currents in Ca2+-activated K+ channels and N-type voltage-gated (KCNA and KCNC) K+ channels. Bupivacaine also inhibits voltage-gated Na+ channels and tandem pore domain (TASK-2/KCNK-5) K+ channels. The compound is cytotoxic at high concentrations inducing apoptosis and/or necrosis by interference with the mitochondrial energy transduction. Shown to inhibit aerobic ATP synthesis by (i) uncoupling of the oxidative phosphorylation (OXPHOS) and (ii) inhibition of the complex I of the respiratory. Other mechanisms include inhibition of the carnitine-acylcarnitine translocase or activation of the mitochondrial permeability transition pore (MPTP). The analgesic effects of bupivicaine are thought to potentially be due to its binding to the prostaglandin E2 receptors, subtype EP1 (PGE2EP1), which inhibits the production of prostaglandins, thereby reducing fever, inflammation, and hyperalgesia. It is employed as cAMP production inhibitor, it acts as a surfactant molecule possessing both hydrophilic and lipophilic properties, adrenergic antagonist and cholinesterase inhibitor.
- Smiles
- CCCCN1CCCCC1C(NC2=C(C)C=CC=C2C)=O.Cl.O
- InChi Key
- HUCIWBPMHXGLFM-UHFFFAOYSA-N
- References
- (1) F. Sztark, et al., Anesthesiology 88, 1340 (1998) , (2) G.L. Weinberg, et al., Anesthesiology 92, 523 (2000) , (3) C.W. Hoenemann, et al., Anesth. Analg. 93, 628 (2001) , (4) W. Irwin, et al., J. Biol. Chem. 277, 12221 (2002) , (5) W.H. Kluge, et al., Scand. J. Clin. Lab Invest. 62, 495 (2002) , (6) A. Unami, et al., J. Toxicol. Sci. 28, 77 (2003) , (7) C.H. Kindler, et al., J. Pharmacol. Exp. Ther. 306, 84 (2003) , (8) J. Nilsson, et al., Biophys. J. 95, 5138 (2008) , (9) O. Cela, et al. , Mitochondrion 10, 487 (2010) , (10) J. Lu, et al., Eur. J. Pharmacol. 657, 51 (2011) , (11) M. Harato, et al., BMC Neurosci. 13, 149 (2012) , (12) P. Martin, et al., Channels 6, 174 (2012) , (13) M.A. Paganelli & G.K. Popescu, J. Neurosci. 35, 831 (2015)
Bupivacaine is an amino amide local anesthetic that decreases current amplitude and inhibits whole cell K+ currents in Ca2+-activated K+ channels and N-type voltage-gated (KCNA and KCNC) K+ channels. Bupivacaine also inhibits voltage-gated Na+ channels and tandem pore domain (TASK-2/KCNK-5) K+ channels. The compound is cytotoxic at high concentrations inducing apoptosis and/or necrosis by interference with the mitochondrial energy transduction. Shown to inhibit aerobic ATP synthesis by (i) uncoupling of the oxidative phosphorylation (OXPHOS) and (ii) inhibition of the complex I of the respiratory. Other mechanisms include inhibition of the carnitine-acylcarnitine translocase or activation of the mitochondrial permeability transition pore (MPTP). The analgesic effects of bupivicaine are thought to potentially be due to its binding to the prostaglandin E2 receptors, subtype EP1 (PGE2EP1), which inhibits the production of prostaglandins, thereby reducing fever, inflammation, and hyperalgesia. It is employed as cAMP production inhibitor, it acts as a surfactant molecule possessing both hydrophilic and lipophilic properties, adrenergic antagonist and cholinesterase inhibitor.
Additional information
| Synonyms | 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide, 1-Butyl-2',6'-pipecoloxylidide |
|---|---|
| Purity | ≥98% (T) |
| Appearance | White to off-white powder |
| CAS-Number | 73360-54-0 |
| Molecular Formula | C18H28N2O · HCl · H2O |
| Molecular Weight | 342.9 |
| Identity | 1H-NMR |
| Solvents | water (10mg/ml), DMSO (20mg/ml), ethanol (20mg/ml), chloroform or acetone (slightly) |
| Smiles | CCCCN1CCCCC1C(NC2=C(C)C=CC=C2C)=O.Cl.O |
| InChi Key | HUCIWBPMHXGLFM-UHFFFAOYSA-N |
| Shipping | AMBIENT |
| Short Term Storage | RT |
| Long Term Storage | RT |
| Handling Advice | Protect from light and moisture. |
| Use / Stability | Stable for at least 2 years after receipt when stored at RT. |
| Hazard statements | H300 + H310 + H330 |
| Precautionary statements | P260-P264-P280-P284-P301 + P310-P302 + P350 |
| GHS Symbol | GHS06 |
| Signal word | Danger |
| RIDADR | UN 2811 6.1 |
| Transportation | Packing Group II |
| References | (1) F. Sztark, et al., Anesthesiology 88, 1340 (1998), (2) G.L. Weinberg, et al., Anesthesiology 92, 523 (2000), (3) C.W. Hoenemann, et al., Anesth. Analg. 93, 628 (2001), (4) W. Irwin, et al., J. Biol. Chem. 277, 12221 (2002), (5) W.H. Kluge, et al., Scand. J. Clin. Lab Invest. 62, 495 (2002), (6) A. Unami, et al., J. Toxicol. Sci. 28, 77 (2003), (7) C.H. Kindler, et al., J. Pharmacol. Exp. Ther. 306, 84 (2003), (8) J. Nilsson, et al., Biophys. J. 95, 5138 (2008), (9) O. Cela, et al. , Mitochondrion 10, 487 (2010), (10) J. Lu, et al., Eur. J. Pharmacol. 657, 51 (2011), (11) M. Harato, et al., BMC Neurosci. 13, 149 (2012), (12) P. Martin, et al., Channels 6, 174 (2012), (13) M.A. Paganelli & G.K. Popescu, J. Neurosci. 35, 831 (2015) |
| Quantity | 1 g, 5 g, Bulk |
