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MedKoo Cat#: 412206 | Name: Trimedoxime bromide
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Description:

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

Trimedoxime bromide is a cholinesterase reactivator used as an antidote in alkyl phosphate poisoning. Trimedoxime bromide, also known as dipyroxime or TMB-4, is an oxime used in the treatment of organophosphate poisoning. It is chemically related to asoxime, pralidoxime, and obidoxime.

Chemical Structure

Trimedoxime bromide
Trimedoxime bromide
CAS#56-97-3 (bromide)

Theoretical Analysis

MedKoo Cat#: 412206

Name: Trimedoxime bromide

CAS#: 56-97-3 (bromide)

Chemical Formula: C15H18Br2N4O2

Exact Mass: 443.9797

Molecular Weight: 446.14

Elemental Analysis: C, 40.38; H, 4.07; Br, 35.82; N, 12.56; O, 7.17

Price and Availability

Size Price Availability Quantity
1g USD 2,950.00 4-6 weeks
2g USD 5,250.00 4-6 weeks
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Related CAS #
6736-02-3 (cation) 56-97-3 (bromide)
Synonym
Trimedoxime bromide; C-434; C434; C 434; TMB-4; dipyroxime;
IUPAC/Chemical Name
1,1'-(propane-1,3-diyl)bis(4-((E)-(hydroxyimino)methyl)pyridin-1-ium) bromide
InChi Key
JHZHWVQTOXIXIV-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H16N4O2.2BrH/c20-16-12-14-2-8-18(9-3-14)6-1-7-19-10-4-15(5-11-19)13-17-21;;/h2-5,8-13H,1,6-7H2;2*1H
SMILES Code
O/N=C/c1cc[n+](CCC[n+]2ccc(/C=N/O)cc2)cc1.[Br-].[Br-]
Appearance
Solid powder
Purity
>95% (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
Certificate of Analysis
View CoA: current batch, Lot#M23P01S20
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 446.14 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.

Recalculate based on batch purity %
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
1: de Castro AA, Polisel DA, Pereira BTL, da Cunha EFF, Kuca K, Nepovimova E, Ramalho TC. Understanding the Interaction Modes and Reactivity of Trimedoxime toward MmAChE Inhibited by Nerve Agents: Theoretical and Experimental Aspects. Int J Mol Sci. 2020 Sep 5;21(18):6510. doi: 10.3390/ijms21186510. PMID: 32899591; PMCID: PMC7554915. 2: Talley TT, Chao CK, Berkman CE, Richardson RJ, Thompson CM. Inhibition of Acetylcholinesterases by Stereoisomeric Organophosphorus Compounds Containing Both Thioester and p-Nitrophenyl Leaving Groups. Chem Res Toxicol. 2020 Sep 21;33(9):2455-2466. doi: 10.1021/acs.chemrestox.0c00236. Epub 2020 Sep 9. PMID: 32833441. 3: Gore A, Neufeld-Cohen A, Egoz I, Baranes S, Gez R, Grauer E, Chapman S, Lazar S. Efficacy of retigabine in ameliorating the brain insult following sarin exposure in the rat. Toxicol Appl Pharmacol. 2020 May 15;395:114963. doi: 10.1016/j.taap.2020.114963. Epub 2020 Mar 21. PMID: 32209366. 4: Chapman S, Grauer E, Gez R, Egoz I, Lazar S. Time dependent dual effect of anti-inflammatory treatments on sarin-induced brain inflammation: Suggested role of prostaglandins. Neurotoxicology. 2019 Sep;74:19-27. doi: 10.1016/j.neuro.2019.05.006. Epub 2019 May 13. PMID: 31095963. 5: Bloch-Shilderman E, Yacov G, Cohen L, Egoz I, Gutman H, Gez R, Rabinovitz I, Nili U. Repetitive antidotal treatment is crucial in eliminating eye pathology, respiratory toxicity and death following whole-body VX vapor exposure in freely moving rats. Arch Toxicol. 2019 May;93(5):1365-1384. doi: 10.1007/s00204-019-02401-0. Epub 2019 Feb 7. PMID: 30729277. 6: Muckova L, Vanova N, Misik J, Herman D, Pejchal J, Jun D. Oxidative stress induced by oxime reactivators of acetylcholinesterase in vitro. Toxicol In Vitro. 2019 Apr;56:110-117. doi: 10.1016/j.tiv.2019.01.013. Epub 2019 Jan 23. PMID: 30682493. 7: Gorecki L, Soukup O, Kucera T, Malinak D, Jun D, Kuca K, Musilek K, Korabecny J. Oxime K203: a drug candidate for the treatment of tabun intoxication. Arch Toxicol. 2019 Mar;93(3):673-691. doi: 10.1007/s00204-018-2377-7. Epub 2018 Dec 18. PMID: 30564897. 8: Malinak D, Nepovimova E, Jun D, Musilek K, Kuca K. Novel Group of AChE Reactivators-Synthesis, In Vitro Reactivation and Molecular Docking Study. Molecules. 2018 Sep 7;23(9):2291. doi: 10.3390/molecules23092291. PMID: 30205495; PMCID: PMC6225275. 9: Caisberger F, Pejchal J, Misik J, Kassa J, Valis M, Kuca K. The benefit of combinations of oximes for the ability of antidotal treatment to counteract sarin-induced brain damage in rats. BMC Pharmacol Toxicol. 2018 Jun 28;19(1):35. doi: 10.1186/s40360-018-0227-0. PMID: 29954446; PMCID: PMC6022407. 10: Muckova L, Pejchal J, Jost P, Vanova N, Herman D, Jun D. Cytotoxicity of acetylcholinesterase reactivators evaluated in vitro and its relation to their structure. Drug Chem Toxicol. 2019 May;42(3):252-256. doi: 10.1080/01480545.2018.1432641. Epub 2018 Feb 9. PMID: 29421945. 11: Pittel Z, Lazar S, Gez R, Chapman S. Early changes in M2 muscarinic acetylcholine receptors (mAChRs) induced by sarin intoxication may be linked to long lasting neurological effects. Neurotoxicology. 2018 Mar;65:248-254. doi: 10.1016/j.neuro.2017.11.002. Epub 2017 Nov 8. PMID: 29128314. 12: Antonijevic E, Kotur-Stevuljevic J, Musilek K, Kosvancova A, Kuca K, Djukic- Cosic D, Spasojevic-Kalimanovska V, Antonijevic B. Effect of six oximes on acutely anticholinesterase inhibitor-induced oxidative stress in rat plasma and brain. Arch Toxicol. 2018 Feb;92(2):745-757. doi: 10.1007/s00204-017-2101-z. Epub 2017 Nov 2. PMID: 29098328. 13: Egoz I, Nili U, Grauer E, Gore A. Optimization of the Ocular Treatment Following Organophosphate Nerve Agent Insult. Toxicol Sci. 2017 Sep 1;159(1):50-63. doi: 10.1093/toxsci/kfx119. PMID: 28903494. 14: Kassa J, Misik J, Hatlapatkova J, Zdarova Karasova J, Sepsova V, Caisberger F, Pejchal J. The Evaluation of the Reactivating and Neuroprotective Efficacy of Two Newly Prepared Bispyridinium Oximes (K305, K307) in Tabun-Poisoned Rats-A Comparison with Trimedoxime and the Oxime K203. Molecules. 2017 Jul 11;22(7):1152. doi: 10.3390/molecules22071152. PMID: 28696367; PMCID: PMC6152392. 15: Kassa J, Misik J, Hatlapatkova J, Zdarova Karasova J. A comparison of neuroprotective efficacy of two novel reactivators of acetylcholinesterase called K920 and K923 with the oxime K203 and trimedoxime in tabun-poisoned rats. Toxicol Mech Methods. 2017 Mar;27(3):236-243. doi: 10.1080/15376516.2016.1275907. Epub 2017 Jan 22. PMID: 28043192. 16: Antonijevic E, Musilek K, Kuca K, Djukic-Cosic D, Vucinic S, Antonijevic B. Therapeutic and reactivating efficacy of oximes K027 and K203 against a direct acetylcholinesterase inhibitor. Neurotoxicology. 2016 Jul;55:33-39. doi: 10.1016/j.neuro.2016.05.006. Epub 2016 May 10. PMID: 27177985. 17: Singh AL, Klick JC, McCracken CE, Hebbar KB. Evaluating Hospice and Palliative Medicine Education in Pediatric Training Programs. Am J Hosp Palliat Care. 2017 Aug;34(7):603-610. doi: 10.1177/1049909116643747. Epub 2016 Apr 26. PMID: 27122617. 18: Kassa J, Hatlapatková J, Žďárová Karasová J. The Evaluation of the Potency of Newly Developed Oximes (K727, K733) and Trimedoxime to Counteract Acute Neurotoxic Effects of Tabun in Rats. Acta Medica (Hradec Kralove). 2015;58(4):135-43. doi: 10.14712/18059694.2016.6. PMID: 26960827. 19: Sharma R, Gupta B, Singh N, Acharya JR, Musilek K, Kuca K, Ghosh KK. Development and Structural Modifications of Cholinesterase Reactivators against Chemical Warfare Agents in Last Decade: A Review. Mini Rev Med Chem. 2015;15(1):58-72. doi: 10.2174/1389557514666141128102837. PMID: 25441834. 20: Kassa J, Sepsova V, Tumova M, Horova A, Musilek K. A comparison of the reactivating and therapeutic efficacy of two newly developed oximes (k727 and k733) with oxime k203 and trimedoxime in tabun-poisoned rats and mice. Basic Clin Pharmacol Toxicol. 2015 Apr;116(4):367-71. doi: 10.1111/bcpt.12327. Epub 2014 Oct 24. PMID: 25225130.