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

• ChemBase ID: 73028
• Molecular Formular: C18H29ClN2O
• Molecular Mass: 324.88866
• Monoisotopic Mass: 324.19684124
• SMILES: c1ccc(c(c1C)NC(=O)C1N(CCCC1)CCCC)C.Cl
• Canonical SMILES: CCCCN1CCCCC1C(=O)Nc1c(C)cccc1C.Cl
• InChI: InChI=1S/C18H28N2O.ClH/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);1H
• InChIKey: SIEYLFHKZGLBNX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride
• IUPAC Traditional name: bupivacaine hydrochloride
• Synonyms: 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide Hydrochloride; dl-1-n-Butylpiperidine-2-carboxylic Acid 2,6-Dimethylanilide Hydrochloride; AH-2250; LAC-43; Carbostesin; Bupivacaine hydrochloride monohydrate; Marcain; Marcaine; Sensorcaine; Vivacaine; Bupivacaine hydrochloride; 1-Butyl-N-[2,6-dimethylphenyl]-2-piperidinecarboxamide; BUPIVACAINE; 1-丁基-N-(2,6-二甲基苯基)-2-哌啶甲酰胺; 布比卡因 盐酸盐

Database IDs

• CAS Number: 18010-40-7; 14252-80-3
• EC Number: 241-917-8
• MDL Number: MFCD00078956
• PubChem SID: 24891830; 162037948
• PubChem CID: 64737

CALCULATED PROPERTIES

• Acid pKa: 13.623539
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.0522962
• LogD (pH = 7.4): 3.8159845
• Log P: 4.5155187
• Molar Refractivity: 90.1933 cm^3
• Polarizability: 34.286346 Å^3
• Polar Surface Area: 32.34 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 249-251°C; 260-265°C

Safety Information

• Storage Condition: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS: TK6125000
• European Hazard Symbols: Toxic (T); Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Australian Hazchem: 2XE
• Risk Statements: 26/27/28; R:25
• Safety Statements: 22-36/37/39-45; S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Product Information

• Purity: ≥99%
• Grade: analytical standard, for drug analysis
• Salt Data: hydrochloride

DETAILS

MP Biomedicals - 02154904

(1-Butyl-N-[2,6-dimethylphenyl]-2-piperidinecarboxamide) Hydrochloride

Selleck Chemicals - S2454

Research Area: Neurological Disease
Biological Activity:
Bupivacaine hydrochloride(Marcain) is a more potent cAMP production inhibitor with an IC50 of 2.3 µM. It more potently inhibited basal cAMP production than either ropivacaine (IC50 = 4 µM) or mepivacaine (IC50 = 32 µM). Similarly, it was as potent as ropivacaine (IC50 = 1.7 µM) and more potent than mepivacaine (IC50 = 8.9 µM) at inhibiting epinephrine-stimulated cAMP production. Bupivacaine (IC50 = 5.3 µM) was only marginally more potent than ropivacaine (IC50 = 9.7 µM) or mepivacaine (IC50 = 6.8 µM) at inhibition of forskolin-stimulated cAMP production. Comparison of epinephrine concentration-response curves in the presence and absence of bupivacaine (0.35, 3.5, and 35 µM ) demonstrated noncompetitive inhibition of cAMP production by the local anesthetic. [1][2]

Sigma Aldrich - B5274

Biochem/physiol Actions
钠通道阻断剂，局部麻醉剂。

Toronto Research Chemicals - B689560

Sodium channel blocker, local anesthetic.

REFERENCES

• http://en.wikipedia.org/wiki/Bupivacaine
• Wilson, T.D., et al.: Anal. Profiles Drug Subs., 19, 59 (1990)
• McClellan, K.J., et al.: Drugs, 56, 355 (1990)