ChemicalBook > CAS DataBase List > (±)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

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

Product Name: (±)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
CAS No.: 38396-39-3
Chemical Name: (±)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide
Synonyms: Bupivacaina;Ah 250;Bucain;Bupivan;Rac-Bupivacaine;Bupivacaine Base CRS;Bupivacaine Free Base;Bupivacaine (SKY 0402);Bupivacaine Base (IHS);Bupivacaine Impurity 37
CBNumber: CB8897837
Molecular Formula: C18H28N2O
Formula Weight: 288.43
MOL File: 38396-39-3.mol

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

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)

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Safety

RIDADR: UN2811
TSCA: Yes
HazardClass: 6.1
Hazardous Substances Data: 38396-39-3(Hazardous Substances Data)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

H310Fatal in contact with skin

H330Fatal if inhaled

Precautionary statements

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P320Specific treatment is urgent (see … on this label).

P330Rinse mouth.

P405Store locked up.

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 16618
Product name: Bupivacaine
Purity: ≥98%
Packaging: 1g
Price: $50
Updated: 2024/03/01

Cayman Chemical

Product number: 16618
Product name: Bupivacaine
Purity: ≥98%
Packaging: 5g
Price: $68
Updated: 2024/03/01

Cayman Chemical

Product number: 16618
Product name: Bupivacaine
Purity: ≥98%
Packaging: 500mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 16618
Product name: Bupivacaine
Purity: ≥98%
Packaging: 25g
Price: $214
Updated: 2024/03/01

TRC

Product number: B689561
Product name: Bupivacaine
Packaging: 1g
Price: $95
Updated: 2021/12/16

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

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

14252-80-3

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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

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

1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboximidic Acid

2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-

Bupivan

(R,S)-Bupivqacaine hydrochloride

rac-(2R*)-N-(2,6-Dimethylphenyl)-1-butyl-2β*-piperidinecarboxamide

(1)-1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

Ah 250

Bupivacaina

Bupivacaine Free Base

Bucain

BUPIVACAINE FREE BASEBUPIVACAINE FREE BASE

Rac-Bupivacaine

Bupivacaine (SKY 0402)

1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboximidicaci

Bupivacaine Base (IHS)

Bupivacaine, 10 mM in DMSO

BUPIVACAINE (NON-STERILE, ACTIVE PHARMACEUTICAL INGREDIENT)

Bupivacaine Base CRS

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

Bupivacaine Impurity 37

38396-39-3