Synonym
Dibucaine; Cinchocaine; Nupercainal; Nupercaine; Sovcaine; Dibucaine Base; NSC 159055; NSC159055; NSC-159055
IUPAC/Chemical Name
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
InChi Key
PUFQVTATUTYEAL-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H29N3O2/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)
SMILES Code
CCCCOC1=NC2=CC=CC=C2C(=C1)C(=O)NCCN(CC)CC
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, not in water
Shelf Life
>2 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
2934.99.9001
Biological target:
Dibucaine (Cinchocaine) 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 |
comments |
| Solubility |
| DMSO |
45.0 |
131.02 |
|
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
343.46
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:
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.
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.
1: Li Y, Li CF, Du LM, Feng JX, Liu HL, Fu YL. A competitive strategy based on cucurbit[7]uril supramolecular interaction for simple and sensitive detection of dibucaine. Talanta. 2015 Jan;132:653-7. doi: 10.1016/j.talanta.2014.09.005. Epub 2014 Sep 11. PubMed PMID: 25476359.
2: Mocanu A, Pasca RD, Tomoaia G, Avranas A, Horovitz O, Tomoaia-Cotisel M. Selective effect of procaine, tetracaine and dibucaine on gold nanoparticles. J Nanosci Nanotechnol. 2012 Dec;12(12):8935-9. PubMed PMID: 23447941.
3: White SH, Brisson CD, Andrew RD. Examining protection from anoxic depolarization by the drugs dibucaine and carbetapentane using whole cell recording from CA1 neurons. J Neurophysiol. 2012 Apr;107(8):2083-95. doi: 10.1152/jn.00701.2011. Epub 2012 Jan 25. PubMed PMID: 22279188.
4: 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. PubMed PMID: 21789251; PubMed Central PMCID: PMC3137632.
5: 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. PubMed PMID: 21731431; PubMed Central PMCID: PMC3127107.
6: 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. PubMed PMID: 21273307; PubMed Central PMCID: PMC3075305.
7: Peropadre A, Fernández Freire P, Herrero O, Pérez Martín JM, Hazen MJ. Cellular responses associated with dibucaine-induced phospholipidosis. Chem Res Toxicol. 2011 Feb 18;24(2):185-92. doi: 10.1021/tx100262c. Epub 2011 Jan 24. PubMed PMID: 21261262.
8: Kang C, Shin SC. Preparation and evaluation of bioadhesive dibucaine gels for enhanced local anesthetic action. Arch Pharm Res. 2010 Aug;33(8):1277-83. doi: 10.1007/s12272-010-0819-8. Epub 2010 Aug 28. PubMed PMID: 20803132.
9: Hanzlicek AS, Van der Merwe D. Dibucaine toxicosis in a dog. J Med Toxicol. 2010 Mar;6(1):44-9. doi: 10.1007/s13181-010-0036-3. PubMed PMID: 20224995; PubMed Central PMCID: PMC3550451.
10: Van Eerdenbrugh B, Fanwick PE, Taylor LS. 2-But-oxy-N-[2-(diethyl-amino)-eth-yl]quinoline-4-carboxamide (dibucaine). Acta Crystallogr Sect E Struct Rep Online. 2010 Nov 17;66(Pt 12):o3189. doi: 10.1107/S1600536810045460. PubMed PMID: 21589483; PubMed Central PMCID: PMC3011580.
