Copper aspirinate

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)

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
CAS Number	23642-01-5 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	83280 N
ECHA InfoCard	100.041.622
PubChem CID	92244
CompTox Dashboard (EPA)	DTXSID4066919
InChI 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
SMILES 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
Chemical formula	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:
Biological half-life	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). N verify (what is YN ?) Infobox references

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]

External links

• IR Spectrum from Eckerd College's Chem Department

Footnotes

1. 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. doi:10.1016/0014-3057(91)90155-H.