Dimetridazole free base | 551-92-8 | 25332-20-1

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

MedKoo CAT#: 329664

CAS#: 551-92-8 (free base)

Description: Dimetridazole is a drug that combats protozoan infections. It is a nitroimidazole class drug. It has been banned by the Canadian government as a livestock feed additive. It used to be commonly added to poultry feed. This led to it being found in eggs. Because of suspicions of it being carcinogenic its use has been legally limited but it is still found in the eggs.

Chemical Structure

Dimetridazole free base

CAS# 551-92-8 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329664
Name: Dimetridazole free base
CAS#: 551-92-8 (free base)
Chemical Formula: C5H7N3O2
Exact Mass: 141.05
Molecular Weight: 141.130
Elemental Analysis: C, 42.55; H, 5.00; N, 29.77; O, 22.67

Price and Availability

Size	Price	Availability
10g	USD 250	2 weeks
25g	USD 450	2 weeks
100g	USD 750	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Dimetridazole; Dimetridazole free base; NSC 226253; RP 8595; Emtryl; Emtrylvet; Emtrymix.

IUPAC/Chemical Name: 1,2-Dimethyl-5-nitroimidazole

InChi Key: IBXPYPUJPLLOIN-UHFFFAOYSA-N

InChi Code: InChI=1S/C5H7N3O2/c1-4-6-3-5(7(4)2)8(9)10/h3H,1-2H3

SMILES Code: O=[N+](C1=CN=C(C)N1C)[O-]

Appearance: Solid powder

Purity: >97% (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: >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

More Info:

Product Data:

Product Data

Instruction:

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Biological target:	Dimetridazole (1,2-Dimethyl-5-nitroimidazole), a nitroimidazole-based antibiotic, combats protozoan infections.
In vitro activity:	The results showed that both the production of pyocyanin and biofilm of P. aeruginosa PAO1 and the tested clinical isolates, including the isolates deficient in producing extracellular proteases, were significantly decreased upon the treatment of Dimetridazole or Ribavirin (Figure 3). These results clearly demonstrated the efficient antivirulence activities of Ribavirin and Dimetridazole on P. aeruginosa isolates. Reference: Front Microbiol. 2022 Aug 15;13:978502. https://pubmed.ncbi.nlm.nih.gov/36046018/
In vivo activity:	TBD

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	39.0	276.34

Preparing Stock Solutions

The following data is based on the product molecular weight 141.13 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. Yuan Y, Yang X, Zeng Q, Li H, Fu R, Du L, Liu W, Zhang Y, Zhou X, Chu Y, Zhang X, Zhao K. Repurposing Dimetridazole and Ribavirin to disarm Pseudomonas aeruginosa virulence by targeting the quorum sensing system. Front Microbiol. 2022 Aug 15;13:978502. doi: 10.3389/fmicb.2022.978502. PMID: 36046018; PMCID: PMC9421001. 2. Zaghdoudi M, Fourcade F, Soutrel I, Floner D, Amrane A, Maghraoui-Meherzi H, Geneste F. Direct and indirect electrochemical reduction prior to a biological treatment for dimetridazole removal. J Hazard Mater. 2017 Aug 5;335:10-17. doi: 10.1016/j.jhazmat.2017.04.028. Epub 2017 Apr 9. PMID: 28414944.
In vitro protocol:	1. Yuan Y, Yang X, Zeng Q, Li H, Fu R, Du L, Liu W, Zhang Y, Zhou X, Chu Y, Zhang X, Zhao K. Repurposing Dimetridazole and Ribavirin to disarm Pseudomonas aeruginosa virulence by targeting the quorum sensing system. Front Microbiol. 2022 Aug 15;13:978502. doi: 10.3389/fmicb.2022.978502. PMID: 36046018; PMCID: PMC9421001. 2. Zaghdoudi M, Fourcade F, Soutrel I, Floner D, Amrane A, Maghraoui-Meherzi H, Geneste F. Direct and indirect electrochemical reduction prior to a biological treatment for dimetridazole removal. J Hazard Mater. 2017 Aug 5;335:10-17. doi: 10.1016/j.jhazmat.2017.04.028. Epub 2017 Apr 9. PMID: 28414944.
In vivo protocol:	TBD

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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1: Zaghdoudi M, Fourcade F, Soutrel I, Floner D, Amrane A, Maghraoui-Meherzi H, Geneste F. Direct and indirect electrochemical reduction prior to a biological treatment for dimetridazole removal. J Hazard Mater. 2017 Aug 5;335:10-17. doi: 10.1016/j.jhazmat.2017.04.028. Epub 2017 Apr 9. PubMed PMID: 28414944.

2: Chen DM, Yu ZB, Sun L, Huang J, Gao LH, Li MJ. [Kinetics and Reactive Species Analysis of Dimetridazole Degradation by TiO2]. Huan Jing Ke Xue. 2015 Nov;36(11):4135-40. Chinese. PubMed PMID: 26911000.

3: Flores-Cano JV, Sánchez-Polo M, Messoud J, Velo-Gala I, Ocampo-Pérez R, Rivera-Utrilla J. Overall adsorption rate of metronidazole, dimetridazole and diatrizoate on activated carbons prepared from coffee residues and almond shells. J Environ Manage. 2016 Mar 15;169:116-25. doi: 10.1016/j.jenvman.2015.12.001. Epub 2015 Dec 28. PubMed PMID: 26731310.

4: Gadaj A, Cooper KM, Karoonuthaisiri N, Furey A, Danaher M. Determination of the persistence of dimetridazole, metronidazole and ronidazole residues in black tiger shrimp (Penaeus monodon) tissue and their stability during cooking. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(2):180-93. doi: 10.1080/19440049.2014.983997. Epub 2014 Dec 17. PubMed PMID: 25372355.

5: Hu C, Deng J, Zhao Y, Xia L, Huang K, Ju S, Xiao N. A novel core-shell magnetic nano-sorbent with surface molecularly imprinted polymer coating for the selective solid phase extraction of dimetridazole. Food Chem. 2014 Sep 1;158:366-73. doi: 10.1016/j.foodchem.2014.02.143. Epub 2014 Mar 6. PubMed PMID: 24731356.

6: Granja RH, Nino AM, Reche KV, Giannotti FM, de Lima AC, Wanschel AC, Salerno AG. Determination and confirmation of metronidazole, dimetridazole, ronidazole and their metabolites in bovine muscle by LC-MS/MS. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2013;30(6):970-6. doi: 10.1080/19440049.2013.787653. Epub 2013 May 24. PubMed PMID: 23701281.

7: Sakamoto M, Takeba K, Sasamoto T, Kusano T, Hayashi H, Kanai S, Kanda M, Nagayama T. Determination of dimetridazole, metronidazole and ronidazole in salmon and honey by liquid chromatography coupled with tandem mass spectrometry. Shokuhin Eiseigaku Zasshi. 2011;52(1):51-8. PubMed PMID: 21383535.

8: Callait-Cardinal MP, Leroux S, Venereau E, Chauve CM, Le Pottier G, Zenner L. Incidence of histomonosis in turkeys in France since the bans of dimetridazole and nifursol. Vet Rec. 2007 Oct 27;161(17):581-5. PubMed PMID: 17965368.

9: Dernburg A, Rogier-Saderne MC, Chauve C, Zenner L. Consequences of the withdrawal of dimetridazole on intestinal parasitism in ducks. Vet Rec. 2005 Jan 29;156(5):148-50. PubMed PMID: 15717397.

10: Dalton JR. Inclusion of dimetridazole in gamebird feeds. Vet Rec. 2000 Apr 29;146(18):535. PubMed PMID: 11321219.

11: Sams MJ, Strutt PR, Barnes KA, Damant AP, Rose MD. Determination of dimetridazole, ronidazole and their common metabolite in poultry muscle and eggs by high performance liquid chromatography with UV detection and confirmatory analysis by atmospheric pressure chemical ionisation mass spectrometry. Analyst. 1998 Dec;123(12):2545-9. PubMed PMID: 10435296.

12: Laing PW. In-feed dimetridazole for gamebirds. Vet Rec. 1998 Jan 3;142(1):24. PubMed PMID: 9460224.

13: Cannavan A, Kennedy DG. Determination of dimetridazole in poultry tissues and eggs using liquid chromatography-thermospray mass spectrometry. Analyst. 1997 Sep;122(9):963-6. PubMed PMID: 9374025.

14: Ré JL, De Méo MP, Laget M, Guiraud H, Castegnaro M, Vanelle P, Duménil G. Evaluation of the genotoxic activity of metronidazole and dimetridazole in human lymphocytes by the comet assay. Mutat Res. 1997 Apr 29;375(2):147-55. PubMed PMID: 9202725.

15: Posyniak A, Semeniuk S, Zmudzki J, Niedzielska J, Biernacki B. Tissue concentration of dimetridazole in laying hens. Food Addit Contam. 1996 Nov-Dec;13(8):871-7. PubMed PMID: 8950108.

16: Dalton P. Use of dimetridazole in gamebirds. Vet Rec. 1996 Oct 19;139(16):399. PubMed PMID: 8913016.

17: Inghelbrecht S, Vermeersch H, Ronsmans S, Remon JP, DeBacker P, Vercruysse J. Pharmacokinetics and anti-trichomonal efficacy of a dimetridazole tablet and water-soluble powder in homing pigeons (Columba livia). J Vet Pharmacol Ther. 1996 Feb;19(1):62-7. PubMed PMID: 8992028.

18: Posyniak A, Semeniuk S, Zmudzki J, Niedzielska J, Biernacki B. Residues of dimetridazole in eggs after treatment of laying hens. Vet Res Commun. 1996;20(2):167-74. PubMed PMID: 8711897.

19: EC bans use of dimetridazole in food animals. Vet Rec. 1995 Sep 2;137(10):230. PubMed PMID: 8533212.

20: Coles BH. Dimetridazole dose for birds. Vet Rec. 1992 Jan 11;130(2):40. PubMed PMID: 1542990.

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Dimetridazole free base featured