| Identification | Back Directory | [Name]
(±)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide | [CAS]
38396-39-3 | [Synonyms]
Ah 250
Bucain
Bupivan
Bupivacaina
Rac-Bupivacaine
Bupivacaine Free Base
Bupivacaine (SKY 0402)
(R,S)-Bupivqacaine hydrochloride
BUPIVACAINE FREE BASEBUPIVACAINE FREE BASE
2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-
(1)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboximidic Acid
rac-(2R*)-N-(2,6-Dimethylphenyl)-1-butyl-2β*-piperidinecarboxamide | [EINECS(EC#)]
253-911-2 | [Molecular Formula]
C18H28N2O | [MDL Number]
MFCD00243007 | [MOL File]
38396-39-3.mol | [Molecular Weight]
288.43 |
| Chemical Properties | Back Directory | [Melting point ]
106-110℃ | [Boiling point ]
423.4±45.0 °C(Predicted) | [density ]
1.032±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO:25.0(Max Conc. mg/mL);86.68(Max Conc. mM)
DMF:30.0(Max Conc. mg/mL);104.01(Max Conc. mM)
Ethanol:30.0(Max Conc. mg/mL);104.01(Max Conc. mM)
Ethanol:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);1.73(Max Conc. mM) | [form ]
Cyrstalline powder | [pka]
14.85±0.70(Predicted) | [Water Solubility ]
Soluble in water, ethanol, chloroform (slightly ), and acetone (slightly ). | [EPA Substance Registry System]
2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)- (38396-39-3) |
| Hazard Information | Back Directory | [Description]
Bupivacaine is a sodium channel blocker and local anesthetic. It inhibits sodium currents in rat dorsal horn neurons in a concentration-dependent manner and inhibits synaptic transmission in rat sympathetic ganglia, increasing the firing threshold when used at a concentration of 200 nM. Bupivacaine (10 μM) blocks cardiac sodium channels in a use-dependent manner and inhibits respiration in cardiac cell mitochondria when palmitoyl-carnitine or acetyl-carnitine are used as substrates (IC50s = 0.78 and 0.37 mM, respectively). It also reduces thermal hyperplasia in a rat model of sciatic ligation injury when 0.6 ml of a 0.5% solution is administered into the perinerve space, and the duration of this effect is extended by co-administration of the NMDA receptor antagonist MK-801 . Formulations containing bupivacaine have been used as local anesthetics for surgery, oral surgery, and dental procedures and for anesthetic purposes in research studies using animals. | [Uses]
Bupivacaine acts as a potent and long-acting local anesthetic agent in vivo. At 100 μM, it has been reported to inhibit the uptake of dopamine in striatal synaptosomes by 47%. | [Definition]
ChEBI: A piperidinecarboxamide obtained by formal condensation of the carboxy group of N-butylpipecolic acid with the amino group of 2,6-dimethylaniline. |
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