Copper aspirinate

Copper aspirinate
Names
IUPAC name
dicopper 2-acetyloxybenzoate
Other names
tetrakis-μ-acetylsalicylato-dicopper(II),
copper(II) aspirinate, cupric acetylsalicylate, cupric aspirinate, cupric aspirin complex
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.041.622 Edit this at Wikidata
  • InChI=1S/4C9H8O4.2Cu/c4*1-6(10)13-8-5-3-2-4-7(8)9(11)12;;/h4*2-5H,1H3,(H,11,12);;/q;;;;2*+2/p-4 ☒N
    Key: BXBJCCCIFADZBU-UHFFFAOYSA-J ☒N
  • InChI=1/4C9H8O4.2Cu/c4*1-6(10)13-8-5-3-2-4-7(8)9(11)12;;/h4*2-5H,1H3,(H,11,12);;/q;;;;2*+2/p-4
    Key: BXBJCCCIFADZBU-XBHQNQODAY
  • CC(=O)Oc1ccccc1C(=O)[O-].CC(=O)Oc1ccccc1C(=O)[O-].CC(=O)Oc1ccccc1C(=O)[O-].CC(=O)Oc1ccccc1C(=O)[O-].[Cu+2].[Cu+2]
  • CC(=O)Oc0ccccc0[C-](O[Cu+2]123)O[Cu+2](O[C-](O1)c0ccccc0OC(=O)C)(O[C-](O2)c0ccccc0OC(=O)C)O[C-](O3)c0ccccc0OC(=O)C
Properties
C36H28Cu2O16
Molar mass 843.69g/mol
Appearance Bright blue crystalline solid.
Melting point 248 to 255 °C (478 to 491 °F; 521 to 528 K) (decomposes)
Pharmacology
Pharmacokinetics:
8.67 h (Human)[Ref#2]
Hazards
NIOSH (US health exposure limits):
PEL (Permissible)
 TWA 1 mg/m3 (as Cu)[1]
REL (Recommended)
 TWA 1 mg/m3 (as Cu)[1]
IDLH (Immediate danger)
 TWA 100 mg/m3 (as Cu)[1]
Related compounds
Other cations
 Zinc aspirinate, Aluminium aspirinate
Related compounds
 Aspirin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Copper(II) aspirinate is an aspirin chelate of copper(II) cations (Cu2+). It is used to treat rheumatoid arthritis.

Picture of Copper II Aspirinate (a.k.a. Copper II Acetylsalicylate)

Preparation

Copper aspirinate can be prepared by several methods. In one route of preparation, an excess of acetylsalicylic acid is dissolved in aqueous sodium carbonate. Sodium hydroxide is not suitable for this purpose, because it will hydrolyse acetylsalicylic acid (ASA) into salicylic acid and sodium acetate.

2 HC9H7O4 + Na2CO3 → 2 NaC9H7O4 + CO2↑ + H2O

The resulting solution is then filtered to remove any undissolved acetylsalicylic acid and is mixed with a solution containing Cu2+ cations (copper(II) sulfate is suitable), precipitating bright blue crystals of copper aspirinate immediately. The crystals can then be filtered from solution, washed, and dried. An excess of acetylsalicylic acid is used in the first step, because it eliminates the possibility of unreacted carbonate anions precipitating the copper in this step.

4 NaC9H7O4 + 2 CuSO4 → C36H28Cu2O16↓ + 2 Na2SO4

Medicinal use

Copper aspirinate has been proven effective as a treatment for rheumatoid arthritis.[2] A pharmacokinetic study in healthy human volunteers supports its enhanced efficacy as compared with aspirin.[3] The studies on animal models suggest that copper aspirinate is very promising in treating against thrombotic diseases and it has all the prospects of success in becoming an antithrombotic drug that prevents and treats thrombotic diseases in humans.[4]

Other uses

The use of copper aspirinate as a pigment in PVC and polystyrene has also been investigated.[5]

Footnotes

  1. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0150". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ "Rheumatoid Arthritis (RA)". Copper Development Association. June 2000. Archived from the original on 2007-02-02. Retrieved 2007-03-05.
  3. ^ MS Iqbal, M Sher, H Pervez & M Saeed (2008). "Pharmacokinetic Study of Copper (II) Acetylsalicylate" Biol. Trace Elem. Res. 124:283–288. doi:10.1007/s12011-008-8146-3
  4. ^ Weiping Liu,corresponding author1 Huizhou Xiong, Yikun Yang Ling Li, Zhiqiang Shen, and Zhihe Chen (1998). "Potential Application of Copper Aspirinate in Preventing and Treating Thromboembolic Diseases". Metal-Based Drugs. 5 (3): 123–126. doi:10.1155/MBD.1998.123. PMC 2365110. PMID 18475833. {{cite journal}}: |author= has generic name (help)CS1 maint: multiple names: authors list (link) CS1 maint: numeric names: authors list (link)
  5. ^ Allan, J R; A Renton; W E Smith; D L Gerrard; J Birnie (1991). "A Study of the Performance of Bis(acetylsalicylate) Copper(II) and the Cobalt(II), Nickel(II) and Copper(II) Complexes of Pyridine-3,4-dicarboxylic Acid as Colouring Materials for Poly(vinyl chloride) and Polystyrene". Eur. Polym. J. 27 (7): 669–672. Bibcode:1991EurPJ..27..669A. doi:10.1016/0014-3057(91)90155-H.