Delmopinol free base | CAS#: 79874-76-3 | surface-active cationic agent

MedKoo Cat#: 581993 | Name: Delmopinol free base

Description:

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

Delmopinol is a surface-active cationic agent. Delmopinol interacts with the early acquired pellicle, the thin layer of saliva polymers and proteins covering teeth and gums, and forms a barrier over teeth and gums. This barrier prevents the microbial adhesion and colonisation on the tooth and gum surface. Delmopinol itself has no bactericidal activity. Delmopinol was approved by FDA under the name Decapinol for the treatment of gingivitis and prevention of periodontitis.

Chemical Structure

Delmopinol free base

CAS#79874-76-3 (free base)

Theoretical Analysis

MedKoo Cat#: 581993

Name: Delmopinol free base

CAS#: 79874-76-3 (free base)

Chemical Formula: C16H33NO2

Exact Mass: 271.2500

Molecular Weight: 271.44

Elemental Analysis: C, 70.80; H, 12.25; N, 5.16; O, 11.79

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Related CAS #

98092-92-3 (HCl) 79874-76-3 (free base) Delmopinol acetate

Synonym

Delmopinol; Decapinol; Decapinolum; Delmopinolum

IUPAC/Chemical Name

2-[3-(4-propylheptyl)morpholin-4-yl]ethanol

InChi Key

QSFOWAYMMZCQNF-UHFFFAOYSA-N

InChi Code

InChI=1S/C16H33NO2/c1-3-6-15(7-4-2)8-5-9-16-14-19-13-11-17(16)10-12-18/h15-16,18H,3-14H2,1-2H3

SMILES Code

CCCC(CCC)CCCC1N(CCO)CCOC1

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

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Delmopinol is a member of morpholines that can be used for its effect on acid adaptation and production in dental plaque biofilms.

In vitro activity:

The aim of this investigation was to determine the antibacterial effect of varying concentrations of delmopinol-HCl on attached as well as on planktonic Streptooccus sanguinis cells in vitro. Total counts of attached bacteria were performed to determine any possible detaching effect by the delmopinol-HCl. The CFU were determined for the planktonic bacteria. Attached as well as planktonic bacteria showed a marked decrease in vitality following exposure to 0.2% delmopinol-HCl. After exposure to 0.05% this was only the case with the attached microorganisms. The total number of attached bacteria was not reduced by the delmopinol treatment. During initial dental biofilm formation, delmopinol-HCl causes a bactericidal effect when applied in concentrations of 0.05% and higher. Reference: Eur J Oral Sci. 2001 Dec;109(6):425-7. https://pubmed.ncbi.nlm.nih.gov/11767281/

In vivo activity:

To study the mode of action of delmopinol, the influence of the compound on the stability of bacterial suspensions, both with and without saliva, and on the zeta-potentials of oral streptococci was studied. The results showed that delmopinol reduced the magnitude of the zeta-potentials, but, in contrast, the colloidal stability of the bacterial suspensions without saliva was increased. The explanation of these observations could be that non-DLVO interaction components, such as repulsive hydration/steric forces, have come into effect at very close distances between two approaching bacterial cells. To judge from the present results, it is possible that delmopinol forms films on bacterial cells in a plaque, thereby facilitating mechanical removal. Reference: Acta Odontol Scand. 1991 Oct;49(5):311-6. https://pubmed.ncbi.nlm.nih.gov/1803851/

	Solvent	mg/mL	mM
Solubility
	H2O	0.2	0.74

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 271.44 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. Neilands J, Troedsson U, Sjödin T, Davies JR. The effect of delmopinol and fluoride on acid adaptation and acid production in dental plaque biofilms. Arch Oral Biol. 2014 Mar;59(3):318-23. doi: 10.1016/j.archoralbio.2013.12.008. Epub 2013 Dec 28. PMID: 24581855. 2. Burgemeister S, Decker EM, Weiger R, Brecx M. Bactericidal effect of delmopinol on attached and planktonic Streptococcus sanguinis cells. Eur J Oral Sci. 2001 Dec;109(6):425-7. doi: 10.1034/j.1600-0722.2001.00121.x. PMID: 11767281. 3. Simonsson T, Arnebrant T, Petersson L, Hvid EB. Influence of delmopinol on bacterial zeta-potentials and on the colloidal stability of bacterial suspensions. Acta Odontol Scand. 1991 Oct;49(5):311-6. doi: 10.3109/00016359109005924. PMID: 1803851.

In vitro protocol:

In vivo protocol:

1. Simonsson T, Arnebrant T, Petersson L, Hvid EB. Influence of delmopinol on bacterial zeta-potentials and on the colloidal stability of bacterial suspensions. Acta Odontol Scand. 1991 Oct;49(5):311-6. doi: 10.3109/00016359109005924. PMID: 1803851.

1: Sjödin T, Movert R, Åström M. Reduced Use of Antibiotics and Nasal Decongestants During Treatment with a Mouthwash Containing Delmopinol. Oral Health Prev Dent. 2023 Nov 2;21:347-356. doi: 10.3290/j.ohpd.b4586769. PMID: 37916545. 2: Waldron C, Eifert J, O'Keefe S, Williams R, Le T. Delmopinol hydrochloride inhibits Campylobacter jejuni on skinless poultry meat, stainless steel, and high-density polyethylene food contact surfaces. Lett Appl Microbiol. 2023 Apr 3;76(4):ovad042. doi: 10.1093/lambio/ovad042. PMID: 37019823. 3: Zhang J, Rustum AM, Adhikari S. Development of a Simple Extraction Procedure and an HPLC Method for the Determination of Delmopinol in a Challenging Rubbery Dental Chew. J AOAC Int. 2023 May 3;106(3):778-785. doi: 10.1093/jaoacint/qsad003. PMID: 36610994. 4: Dovrat S, Kashi-Zagdoun E, Soufiev Z, Mendelson E, Schlossberg T. The Solution Is a Solution. Isr Med Assoc J. 2022 Feb;24(2):80-84. PMID: 35187895. 5: Zhuang J, Rustum AM. Development and Validation of a Stability-Indicating Reversed-Phase Ultra High Pressure Liquid Chromatography Method for Assay of Delmopinol Hydrochloride and Estimation of Its Related Substances in Commercial Bulk Batches. J Chromatogr Sci. 2022 Nov 5;60(9):880-886. doi: 10.1093/chromsci/bmab133. PMID: 34894125. 6: Philip J, Buijs MJ, Pappalardo VY, Crielaard W, Brandt BW, Zaura E. The microbiome of dental and peri-implant subgingival plaque during peri-implant mucositis therapy: A randomized clinical trial. J Clin Periodontol. 2022 Jan;49(1):28-38. doi: 10.1111/jcpe.13566. Epub 2021 Nov 3. PMID: 34664294; PMCID: PMC9298297. 7: Komine A, Yamaguchi E, Okamoto N, Yamamoto K. Virucidal activity of oral care products against SARS-CoV-2 in vitro. J Oral Maxillofac Surg Med Pathol. 2021 Jul;33(4):475-477. doi: 10.1016/j.ajoms.2021.02.002. Epub 2021 Feb 22. PMID: 33643836; PMCID: PMC7898974. 8: Sjödin T, Diogo Löfgren C, Glantz PO, Christersson C. Delmopinol - adsorption to and absorption through the oral mucosa. Acta Odontol Scand. 2020 Nov;78(8):572-579. doi: 10.1080/00016357.2020.1758772. Epub 2020 Apr 29. PMID: 32348171. 9: Philip J, Laine ML, Wismeijer D. Adjunctive effect of mouthrinse on treatment of peri-implant mucositis using mechanical debridement: A randomized clinical trial. J Clin Periodontol. 2020 Jul;47(7):883-891. doi: 10.1111/jcpe.13295. Epub 2020 May 27. PMID: 32315444; PMCID: PMC7317778. 10: Tartaglia GM, Tadakamadla SK, Connelly ST, Sforza C, Martín C. Adverse events associated with home use of mouthrinses: a systematic review. Ther Adv Drug Saf. 2019 Sep 23;10:2042098619854881. doi: 10.1177/2042098619854881. PMID: 31579502; PMCID: PMC6759706. 11: Sjödin T. The pH-dependent effect of cationic and non-ionic delmopinol on planktonic and biofilm bacteria. Arch Oral Biol. 2019 Jun;102:101-105. doi: 10.1016/j.archoralbio.2019.03.014. Epub 2019 Apr 6. PMID: 30981076. 12: Levin L, Barbu H, Kurgan S, Comăneanu RM, Referendaru D, Lorean A. Evaluation of 0.2% delmopinol mouth rinse for prevention of peri-implant mucositis and peri-implantitis: A randomized controlled canine study. Clin Implant Dent Relat Res. 2019 Feb;21(1):46-51. doi: 10.1111/cid.12692. Epub 2018 Nov 15. PMID: 30444075. 13: Saucedo-Alderete RO, Eifert JD, Boyer RR, Williams RC, Welbaum GE. Delmopinol hydrochloride reduces Salmonella on cantaloupe surfaces. Food Sci Nutr. 2017 Dec 15;6(2):373-380. doi: 10.1002/fsn3.564. PMID: 29564104; PMCID: PMC5849904. 14: Reddy R, Palaparthy R, Durvasula S, Koppolu P, Elkhatat E, Assiri KAR, Abdulrahman Saad AAS. Gingivitis and plaque prevention using three commercially available dentifrices: A comparative clinical and microbiological randomized control parallel study. Int J Pharm Investig. 2017 Jul-Sep;7(3):111-118. doi: 10.4103/jphi.JPHI_41_17. PMID: 29184822; PMCID: PMC5680645. 15: LuIs HS, Luis LS, Bernardo M. In vitro study of the effect of an essential oil and a delmopinol mouth rinse on dental plaque bacteria. Indian J Dent Res. 2016 Nov-Dec;27(6):648-651. doi: 10.4103/0970-9290.199602. PMID: 28169264. 16: Tartaglia GM, Kumar S, Fornari CD, Corti E, Connelly ST. Mouthwashes in the 21st century: a narrative review about active molecules and effectiveness on the periodontal outcomes. Expert Opin Drug Deliv. 2017 Aug;14(8):973-982. doi: 10.1080/17425247.2017.1260118. Epub 2016 Nov 20. PMID: 27835926. 17: Escribano M, Figuero E, Martín C, Tobías A, Serrano J, Roldán S, Herrera D. Efficacy of adjunctive anti-plaque chemical agents: a systematic review and network meta-analyses of the Turesky modification of the Quigley and Hein plaque index. J Clin Periodontol. 2016 Dec;43(12):1059-1073. doi: 10.1111/jcpe.12616. Epub 2016 Oct 10. PMID: 27531174. 18: Jafer M, Patil S, Hosmani J, Bhandi SH, Chalisserry EP, Anil S. Chemical Plaque Control Strategies in the Prevention of Biofilm-associated Oral Diseases. J Contemp Dent Pract. 2016 Apr 1;17(4):337-43. doi: 10.5005/jp- journals-10024-1851. PMID: 27340170. 19: Sjödin T, Nilner K, Sparre B, Bernet C, Åström M. A clinical and microbiological study on the enantiomers of delmopinol. Acta Odontol Scand. 2016 Jul;74(5):355-61. doi: 10.3109/00016357.2016.1151546. Epub 2016 Mar 3. PMID: 26940371. 20: Ready D, Theodoridis G, Green I, Ciric L, Pratten J, Tay W, McDonald A. In vitro evaluation of the antibiofilm properties of chlorhexidine and delmopinol on dental implant surfaces. Int J Antimicrob Agents. 2015 Jun;45(6):662-6. doi: 10.1016/j.ijantimicag.2015.01.020. Epub 2015 Mar 14. PMID: 25963339.