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MedKoo Cat#: 461170 | Name: Coumachlor

Description:

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

Coumachlor is a first genereation anticoagulant rodenticide which blocks formation of prothrombin and inhibits blood coagulation causing death by internal haemorrhage.

Chemical Structure

Coumachlor
Coumachlor
CAS#81-82-3

Theoretical Analysis

MedKoo Cat#: 461170

Name: Coumachlor

CAS#: 81-82-3

Chemical Formula: C19H15ClO4

Exact Mass: 342.0659

Molecular Weight: 342.77

Elemental Analysis: C, 66.58; H, 4.41; Cl, 10.34; O, 18.67

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Synonym
Coumachlor; Ratilan; Tomorin; p-Chlorowarfarin; (±)-p-Chlorowarfarin; (±)-Coumachlor; Racemic coumachlor
IUPAC/Chemical Name
3-(1-(4-chlorophenyl)-3-oxobutyl)-4-hydroxy-2H-chromen-2-one
InChi Key
DEKWZWCFHUABHE-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H15ClO4/c1-11(21)10-15(12-6-8-13(20)9-7-12)17-18(22)14-4-2-3-5-16(14)24-19(17)23/h2-9,15,22H,10H2,1H3
SMILES Code
CC(CC(C1=CC=C(C=C1)Cl)C2=C(C3=CC=CC=C3OC2=O)O)=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 342.77 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: WANNTORP H. Studies on chemical determination of warfar in and coumachlor and their toxicity for dog and swine. Acta Pharmacol Toxicol (Copenh). 1959;16(Suppl 2):1-123. PubMed PMID: 13842849. 2: Gómez-Canela C, Lacorte S. Comprehensive characterization of anticoagulant rodenticides in sludge by liquid chromatography-tandem mass spectrometry. Environ Sci Pollut Res Int. 2016 Aug;23(15):15739-48. doi: 10.1007/s11356-016-6743-9. Epub 2016 May 4. PubMed PMID: 27146526. 3: Muscarella M, Armentano A, Iammarino M, Palermo C, Amorena M. Anticoagulant rodenticide poisoning in animals of Apulia and Basilicata, Italy. Vet Ital. 2016 Jun 30;52(2):153-9. doi: 10.12834/VetIt.118.333.3. PubMed PMID: 27393877. 4: Mesban HA, Tayeb EH, Mourad AK, Younis LK, el Zaher MA, Aly MT. Toxicology and histopathology of some rodenticides and palatable food items combinations on the common mice Mus musculus var. albus in Egypt. Commun Agric Appl Biol Sci. 2003;68(4 Pt B):771-87. PubMed PMID: 15151313. 5: Schaff JE, Montgomery MA. An HPLC-HR-MS-MS method for identification of anticoagulant rodenticides in blood. J Anal Toxicol. 2013 Jul-Aug;37(6):321-5. doi: 10.1093/jat/bkt036. Epub 2013 May 10. PubMed PMID: 23667199. 6: Stavrou IJ, Breitbach ZS, Kapnissi-Christodoulou CP. Combined use of cyclofructans and an amino acid ester-based ionic liquid for the enantioseparation of huperzine A and coumarin derivatives in CE. Electrophoresis. 2015 Dec;36(24):3061-8. doi: 10.1002/elps.201500367. Epub 2015 Oct 7. PubMed PMID: 26444144. 7: DAM H, SØNDERGAARD E. Comparison of the anticoagulant action of 3-(alpha-p-chlorphenyl-beta-acetylethyl)-4-hydroxycoumarin (coumachlor) and dicoumarol in chicks and rats. Acta Pharmacol Toxicol (Copenh). 1953;9(2):137-47. PubMed PMID: 13079850. 8: Shimshoni JA, Soback S, Cuneah O, Shlosberg A, Britzi M. New validated multiresidue analysis of six 4-hydroxy-coumarin anticoagulant rodenticides in hen eggs. J Vet Diagn Invest. 2013 Nov;25(6):736-43. doi: 10.1177/1040638713501510. Epub 2013 Sep 30. PubMed PMID: 24081927. 9: Kostova I, Manolov I, Karaivanova M. Synthesis, physicochemical characterization, and cytotoxic screening of new zirconium complexes with coumarin derivatives. Arch Pharm (Weinheim). 2001 May;334(5):157-62. PubMed PMID: 11413821. 10: Luces CA, Warner IM. Achiral and chiral separations using MEKC, polyelectrolyte multilayer coatings, and mixed mode separation techniques with molecular micelles. Electrophoresis. 2010 Mar;31(6):1036-43. doi: 10.1002/elps.200900508. PubMed PMID: 20155738; PubMed Central PMCID: PMC4197839. 11: Hou J, Zheng J, Shamsi SA. Separation and determination of warfarin enantiomers in human plasma using a novel polymeric surfactant for micellar electrokinetic chromatography-mass spectrometry. J Chromatogr A. 2007 Aug 3;1159(1-2):208-16. Epub 2007 Apr 21. PubMed PMID: 17499757; PubMed Central PMCID: PMC2748864. 12: Zheng J, Shamsi SA. Brush-type chiral stationary phase for enantioseparation of acidic compounds. Optimization of chiral capillary electrochromatographic parameters. J Chromatogr A. 2003 Jul 11;1005(1-2):177-87. PubMed PMID: 12924792. 13: Gallocchio F, Basilicata L, Benetti C, Angeletti R, Binato G. Multi-residue determination of eleven anticoagulant rodenticides by high-performance liquid chromatography with diode array/fluorimetric detection: investigation of suspected animal poisoning in the period 2012-2013 in north-eastern Italy. Forensic Sci Int. 2014 Nov;244:63-9. doi: 10.1016/j.forsciint.2014.08.012. Epub 2014 Aug 20. PubMed PMID: 25195128. 14: Lao W, Gan J. Characterization of warfarin unusual peak profiles on oligoproline chiral high performance liquid chromatography columns. J Chromatogr A. 2010 Oct 15;1217(42):6545-54. doi: 10.1016/j.chroma.2010.08.066. Epub 2010 Sep 16. PubMed PMID: 20846657. 15: Brown NA, Müller WE. Binding of coumarin anticoagulants to human and bovine serum albumin. Circular dichroism studies. Pharmacology. 1978;17(4):233-8. PubMed PMID: 567809. 16: Maršálek P, Modrá H, Doubková V, Večerek V. Simultaneous determination of ten anticoagulant rodenticides in tissues by column-switching UHPLC-ESI-MS/MS. Anal Bioanal Chem. 2015 Oct;407(25):7849-54. doi: 10.1007/s00216-015-8954-1. Epub 2015 Aug 18. PubMed PMID: 26280206. 17: Fauconnet V, Pouliquen H, Pinault L. Reversed-phase HPLC determination of eight anticoagulant rodenticides in animal liver. J Anal Toxicol. 1997 Nov-Dec;21(7):548-53. PubMed PMID: 9399124. 18: Armentano A, Iammarino M, Lo Magro S, Muscarella M. Validation and application of multi-residue analysis of eight anticoagulant rodenticides by high-performance liquid chromatography with fluorimetric detection. J Vet Diagn Invest. 2012 Mar;24(2):307-11. doi: 10.1177/1040638711433354. PubMed PMID: 22379046. 19: Manolov I, Kostova I, Netzeva T, Konstantinov S, Karaivanova M. Cytotoxic activity of cerium complexes with coumarin derivatives. Molecular modeling of the ligands. Arch Pharm (Weinheim). 2000 Apr;333(4):93-8. PubMed PMID: 10816901. 20: Chernonosov A. Quantification of Warfarin in Dried Rat Plasma Spots by High-Performance Liquid Chromatography with Tandem Mass Spectrometry. J Pharm (Cairo). 2016;2016:6053295. doi: 10.1155/2016/6053295. Epub 2016 Dec 12. PubMed PMID: 28058133; PubMed Central PMCID: PMC5183798.

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