| 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) | [color ]
White to off-white | [Water Solubility ]
Soluble in water, ethanol, chloroform (slightly ), and acetone (slightly ). | [InChI]
InChI=1S/C18H28N2O/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) | [InChIKey]
LEBVLXFERQHONN-UHFFFAOYSA-N | [SMILES]
N1(CCCC)CCCCC1C(NC1=C(C)C=CC=C1C)=O | [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. | [Synthesis]
General procedure for the synthesis of free base from bupivacaine hydrochloride: first, 5 g of bupivacaine hydrochloride was dissolved in 195 g of USP grade pure water. Subsequently, about 15 ml of 1.0 N sodium hydroxide solution was slowly added and the pH was adjusted to 9.5. After completion of the reaction, the resulting precipitate was collected by filtration and washed with pure water. Next, the solid was re-dispersed in 50 ml of pure water, stirred for 15 minutes and then filtered and washed again. The above dispersion, filtration and washing operations were repeated. Finally, the resulting material was dried at 40 °C for 72 hours. | [IC 50]
NMDA Receptor | [References]
[1] Patent: WO2008/88756, 2008, A1. Location in patent: Page/Page column 30-31
[2] Patent: WO2003/99293, 2003, A1. Location in patent: Page 10
[3] Patent: US2006/78606, 2006, A1. Location in patent: Page/Page column 4
[4] Organic Process Research and Development, 2000, vol. 4, # 6, p. 530 - 533 |
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