(±)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical Properties

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)

pka

14.85±0.70(Predicted)

form 

Cyrstalline powder

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)

Safety Information

RIDADR 

UN2811

TSCA 

Yes

HazardClass 

6.1

Hazardous Substances Data

38396-39-3(Hazardous Substances Data)

(±)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Usage And Synthesis

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

(±)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide (38396-39-3)Related Product Information

• Bupivacaine Hydrochloride
• 2,6-PIPECOLINOXYLIDIDE HYDROCHLORIDE
• BUPIVACAINE N-OXIDE
• Levobupivacaine hydrochloride
• Bupivacaine Impurity
• Bupivacaine Impurity
• N-(3,5-dimethylphenyl)picolinamide
• Levobupivacaine hydrochloride
• Bupivacaine IMpurity A
• Bupivacaine hydrochloride
• (R)-(+)-BUPIVACAINE HCL
• Bupivacaine IMpurity F
• Bupivacaine-d9
• Bupivacaine Impurity
• Bupivacaine EP Impurity C
• Bupivacaine-(butyl-1-13C)
• Bupivacaine IMpurity C
• Bupivacaine hydrochloride monohydrate