Desbutylbupivacaine | 15883-20-2

MedKoo Cat#: 581642 | Name: Desbutylbupivacaine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Desbutylbupivacaine also known as N-Desbutyl Bupivacaine, it is a major metabolite of Bupivacaine.

Chemical Structure

Desbutylbupivacaine

CAS#15883-20-2

Theoretical Analysis

MedKoo Cat#: 581642

Name: Desbutylbupivacaine

CAS#: 15883-20-2

Chemical Formula: C14H20N2O

Exact Mass: 232.1576

Molecular Weight: 232.33

Elemental Analysis: C, 72.38; H, 8.68; N, 12.06; O, 6.89

Price and Availability

Size	Price	Availability	Quantity
5g	USD 250.00	2 Weeks
25g	USD 450.00	2 Weeks

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Synonym

Desbutylbupivacaine; Debutylbupivacaine; Demethylmepivacaine; N-Desbutylbupivacaine; 2',6'-Pipecolylxylidine.

IUPAC/Chemical Name

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

InChi Key

SILRCGDPZGQJOQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C14H20N2O/c1-10-6-5-7-11(2)13(10)16-14(17)12-8-3-4-9-15-12/h5-7,12,15H,3-4,8-9H2,1-2H3,(H,16,17)

SMILES Code

O=C(C1NCCCC1)NC2=C(C)C=CC=C2C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

A sodium channel blocker and local anesthetic.

In vitro activity:

Bupivacaine suppressed proliferation and induced apoptosis of HepG2 and SNU-449 cells in a time- and dose-dependent manner. Bupivacaine treatment also decreased colony formation, migration, and invasion of HepG2 and SNU-449 cells. Reference: J Biochem Mol Toxicol. 2021 Aug 2:e22871. https://pubmed.ncbi.nlm.nih.gov/34338398/

In vivo activity:

CAL-27 cells were subcutaneously injected to form xenograft tumors in vivo. The results showed that tumor weight and volume treated with 40 µmol/kg Bupi (bupivacaine) were obviously lower compared with the control group (Figure 7A,B). The apoptotic cells were increased, and the number of Ki67+ expression was decreased (Figure 7C,D,E). Neferine treatment also down-regulated the expression of SOX2, NANOG, and OCT4 proteins (Figure 7F). Reference: Ann Transl Med. 2021 May; 9(10): 839. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8184410/

Preparing Stock Solutions

The following data is based on the product molecular weight 232.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Wang L, Guo W, Guan H, Yan N, Cai X, Zhu L. Local anesthetic bupivacaine inhibits proliferation and metastasis of hepatocellular carcinoma cells via suppressing PI3K/Akt and MAPK signaling. J Biochem Mol Toxicol. 2021 Aug 2:e22871. doi: 10.1002/jbt.22871. Epub ahead of print. PMID: 34338398. 2. Gu JH, Liu CC, Xie JL, Ma B, Cui SM, Yang GZ, He SC. The Local Anesthetic Bupivacaine Inhibits the Progression of Non-Small Cell Lung Cancer by Inducing Autophagy Through Akt/mTOR Signaling. Front Oncol. 2021 Mar 11;11:616445. doi: 10.3389/fonc.2021.616445. PMID: 33777755; PMCID: PMC7991299. 3. Wang Z, Zhang J, Wen Y, Wang P, Fan L. Bupivacaine inhibits the malignant biological behavior of oral squamous cell carcinoma cells by inhibiting the activation of ERK1/2 and STAT3. Ann Transl Med. 2021 May;9(10):839. doi: 10.21037/atm-21-1414. PMID: 34164473; PMCID: PMC8184410. 4. Liu B, Yan X, Hou Z, Zhang L, Zhang D. Impact of Bupivacaine on malignant proliferation, apoptosis and autophagy of human colorectal cancer SW480 cells through regulating NF-κB signaling path. Bioengineered. 2021 Dec;12(1):2723-2733. doi: 10.1080/21655979.2021.1937911. PMID: 34151717.

In vitro protocol:

In vivo protocol:

1. Wang Z, Zhang J, Wen Y, Wang P, Fan L. Bupivacaine inhibits the malignant biological behavior of oral squamous cell carcinoma cells by inhibiting the activation of ERK1/2 and STAT3. Ann Transl Med. 2021 May;9(10):839. doi: 10.21037/atm-21-1414. PMID: 34164473; PMCID: PMC8184410. 2. Liu B, Yan X, Hou Z, Zhang L, Zhang D. Impact of Bupivacaine on malignant proliferation, apoptosis and autophagy of human colorectal cancer SW480 cells through regulating NF-κB signaling path. Bioengineered. 2021 Dec;12(1):2723-2733. doi: 10.1080/21655979.2021.1937911. PMID: 34151717.

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