Dibucaine HCl | CAS#61-12-1 | local anesthetic

MedKoo Cat#: 563317 | Name: Dibucaine HCl

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Description:

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

Dibucaine HCl is a long-acting local anesthetic.

Chemical Structure

Dibucaine HCl

CAS#61-12-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 563317

Name: Dibucaine HCl

CAS#: 61-12-1 (HCl)

Chemical Formula: C20H30ClN3O2

Exact Mass: 0.0000

Molecular Weight: 379.92

Elemental Analysis: C, 63.23; H, 7.96; Cl, 9.33; N, 11.06; O, 8.42

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 weeks
5g	USD 550.00	2 weeks

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Related CAS #

61-12-1 (HCl) 85-79-0 (free base)

Synonym

Dibucaine HCl; Dibucaine Hydrochloride; Cinchocaine hydrochloride; Cincaine chloride; Cincain; Nupercainal; Nupercaine; Sovcaine;

IUPAC/Chemical Name

2-Butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide hydrochloride

InChi Key

IVHBBMHQKZBJEU-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H29N3O2.ClH/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3;/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24);1H

SMILES Code

O=C(C1=CC(OCCCC)=NC2=CC=CC=C12)NCCN(CC)CC.[H]Cl

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

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dibucaine hydrochloride (Cinchocaine hydrochloride) is a sodium channel and SChE inhibitor.

In vitro activity:

Effects of dibucaine on depolarization of ΔΨm in platelets were investigated by flow cytometry with the cell-permeable lipophilic cationic dye TMRE. Figure 1a and b demonstrated clearly that dibucaine, but not the vehicle control DMSO, dose-dependently elicited depolarization of ΔΨm in platelets, as monitored by decreased fluorescence in TMRE-stained platelets, and an increase of depolarized platelets. To further investigate whether dibucaine can elicit platelet apoptosis through the mitochondria-mediated pathway, the expression profiles of the Bcl-2 family proteins including Bax, Bak, Bcl-2, and Bcl-XL were analyzed. As shown in Figure 1c and d, the expression levels of pro-apoptotic proteins Bax and Bak increased significantly in platelets following dibucaine induction. Conversely, decreased expression levels of anti-apoptotic proteins Bcl-2 and Bcl-XL were detected simultaneously, consistent with previous studies. In addition, there was an obvious increase in mitochondrial membrane-bound Bax. Taken together, these data indicate that dibucaine induces platelet apoptosis and platelet dysfunction. Reference: Int J Mol Sci. 2011; 12(4): 2125–2137. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3127107/

In vivo activity:

Dibucaine was administered intravenously at 2.5 mg/kg in a mouse stroke model. Dibucaine was administered immediately after the onset of photothrombotically-induced spreading depolarization. Though dibucaine did not inhibit the occurrence of spontaneous spreading depolarizations, dendritic structure remained remarkably stable following recovery from initial induced spreading depolarization (Fig. 3B). Dibucaine significantly reduced the percentage of spontaneous spreading depolarizations that were temporally correlated with dendritic beading (Fig. 3C). Intriguingly, in a subset of 4 mice in which dibucaine injection was delayed until 30 min after photothrombotically-induced initial spreading depolarization, no beading was seen following dibucaine administration. Additionally, dibucaine treatment did not affect the quantitative features of spontaneous spreading depolarizations (p>0.05, Mann–Whitney U test, data not shown). Nevertheless, dibucaine-treated mice had significantly fewer incidents of terminal dendritic beading (i.e. beading without further recovery), occurring in just 1 of 11 mice (compared to 13 of 17 control mice). Reference: PLoS One. 2011;6(7):e22351. https://pubmed.ncbi.nlm.nih.gov/21789251/

	Solvent	mg/mL	mM
Solubility
	DMSO	93.0	244.79
	H2O	88.0	231.63

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 379.92 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. Douglas HA, Callaway JK, Sword J, Kirov SA, Andrew RD. Potent inhibition of anoxic depolarization by the sodium channel blocker dibucaine. J Neurophysiol. 2011 Apr;105(4):1482-94. doi: 10.1152/jn.00817.2010. Epub 2011 Jan 27. PMID: 21273307; PMCID: PMC3075305. 2. Zhang W, Liu J, Sun R, Zhao L, Du J, Ruan C, Dai K. Calpain activator dibucaine induces platelet apoptosis. Int J Mol Sci. 2011;12(4):2125-37. doi: 10.3390/ijms12042125. Epub 2011 Mar 25. PMID: 21731431; PMCID: PMC3127107. 3. Risher WC, Lee MR, Fomitcheva IV, Hess DC, Kirov SA. Dibucaine mitigates spreading depolarization in human neocortical slices and prevents acute dendritic injury in the ischemic rodent neocortex. PLoS One. 2011;6(7):e22351. doi: 10.1371/journal.pone.0022351. Epub 2011 Jul 15. PMID: 21789251; PMCID: PMC3137632.

In vitro protocol:

In vivo protocol:

1. Risher WC, Lee MR, Fomitcheva IV, Hess DC, Kirov SA. Dibucaine mitigates spreading depolarization in human neocortical slices and prevents acute dendritic injury in the ischemic rodent neocortex. PLoS One. 2011;6(7):e22351. doi: 10.1371/journal.pone.0022351. Epub 2011 Jul 15. PMID: 21789251; PMCID: PMC3137632.

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