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Revision as of 07:10, 13 March 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit Latest revision as of 05:42, 23 November 2024 edit undoCitation bot (talk | contribs)Bots5,391,530 edits Added bibcode. | Use this bot. Report bugs. | Suggested by ChemicalBear | Category:Salicylates | #UCB_Category 5/13 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 388684911
| Watchedfields = changed
⚫ | ImageFile = Copper_aspirinate.jpg
⚫ | verifiedrevid = 418579364
| ImageSize =
⚫ | ImageFile1 = Copper_aspirinate.jpg
| ImageFile2 = Cu2(asp)4.png
| ImageSize2 = | ImageSize1 =
| ImageFile3 = Copper(II)-aspirinate-3D-balls.png | ImageFile2 = Cu2(asp)4.png
| IUPACName = dicopper 2-acetyloxybenzoate | ImageSize2 =
| IUPACName = dicopper 2-acetyloxybenzoate
| OtherNames = tetrakis-μ-acetylsalicylato-dicopper(II),<br />copper(II) aspirinate, cupric acetylsalicylate, cupric aspirinate, cupric aspirin complex | OtherNames = tetrakis-μ-acetylsalicylato-dicopper(II),<br />copper(II) aspirinate, cupric acetylsalicylate, cupric aspirinate, cupric aspirin complex
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| Abbreviations = | Abbreviations =
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 23642-01-5 | CASNo = 23642-01-5
| EINECS = | EINECS =
| PubChem = 92244 | PubChem = 92244
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ | SMILES = CC(=O)OC1=CC=CC=C1C(=O).CC(=O)OC1=<br />CC=CC=C1C(=O).CC(=O)OC1=CC=CC=C1C(=O)<br />.CC(=O)OC1=CC=CC=C1C(=O)..
| ChemSpiderID = 83280
⚫ | InChI = 1/4C9H8O4.2Cu/c4*1-6(10)13-8-5-3<br />-2-4-7(8)9(11)12;;/h4*2-5H,1H3,(H,11,12);<br />;/q;;;;2*+2/p-4/f4C9H7O4.2Cu/q4*-1;2m
⚫ | SMILES = CC(=O)Oc1ccccc1C(=O).CC(=O)Oc1ccccc1C(=O).CC(=O)Oc1ccccc1C(=O).CC(=O)Oc1ccccc1C(=O)..
⚫ | 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
| InChIKey = BXBJCCCIFADZBU-XBHQNQODAY
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = BXBJCCCIFADZBU-UHFFFAOYSA-J
| RTECS = | RTECS =
| MeSHName = | MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = | ChEBI =
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = | KEGG =
| SMILES1 = CC(=O)Oc0ccccc0(O123)O(O(O1)c0ccccc0OC(=O)C)(O(O2)c0ccccc0OC(=O)C)O(O3)c0ccccc0OC(=O)C
| ATCCode_prefix =
}}
| ATCCode_suffix =
⚫ | Section2 = {{Chembox Properties
| ATC_Supplemental =}}
⚫ | Section2 = {{Chembox Properties
| Formula = C<sub>36</sub>H<sub>28</sub>Cu<sub>2</sub>O<sub>16</sub> | Formula = C<sub>36</sub>H<sub>28</sub>Cu<sub>2</sub>O<sub>16</sub>
| MolarMass = 843.69g/mol | MolarMass = 843.69g/mol
| Appearance = Bright blue crystalline solid. | Appearance = Bright blue crystalline solid.
| Density = | Density =
| MeltingPt = 248-255°C (decomp.) | MeltingPtC = 248 to 255
| MeltingPt_notes = (decomposes)
| Melting_notes =
| BoilingPt = | BoilingPt =
| Boiling_notes = | BoilingPt_notes =
| Solubility = | Solubility =
| SolubleOther = | SolubleOther =
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| pKa = | pKa =
| pKb = }} | pKb = }}
| Section3 = {{Chembox Structure | Section3 = {{Chembox Structure
| CrystalStruct = | CrystalStruct =
| Coordination = | Coordination =
| MolShape = }} | MolShape = }}
| Section4 = {{Chembox Thermochemistry | Section4 = {{Chembox Thermochemistry
| DeltaHf = | DeltaHf =
| DeltaHc = | DeltaHc =
| Entropy = | Entropy =
| HeatCapacity = }} | HeatCapacity = }}
| Section5 = {{Chembox Pharmacology | Section5 = {{Chembox Pharmacology
| AdminRoutes = | AdminRoutes =
| Bioavail = | Bioavail =
| Metabolism = | Metabolism =
| HalfLife = | HalfLife = 8.67 h (Human)
| ProteinBound = | ProteinBound =
| Excretion = | Excretion =
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| Legal_AU = | Legal_AU =
| Legal_CA = | Legal_CA =
| Pregnancy_category =
| PregCat =
| PregCat_AU = | Pregnancy_AU =
}}
| PregCat_US = }}
| Section6 = {{Chembox Explosive | Section6 = {{Chembox Explosive
| ShockSens = | ShockSens =
| FrictionSens = | FrictionSens =
| ExplosiveV = | DetonationV =
| REFactor = }} | REFactor = }}
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
| EUClass =
| EUIndex =
| MainHazards = | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| NFPA-O = | NFPA-S =
| RPhrases =
| SPhrases =
| RSPhrases =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| ExploLimits = | ExploLimits =
| PEL = TWA 1 mg/m<sup>3</sup> (as Cu)<ref name=PGCH>{{PGCH|0150}}</ref>
| PEL = }}
| REL = TWA 1 mg/m<sup>3</sup> (as Cu)<ref name=PGCH/>
⚫ | Section8 = {{Chembox Related
| IDLH = TWA 100 mg/m<sup>3</sup> (as Cu)<ref name=PGCH/>
}}
⚫ | Section8 = {{Chembox Related
| OtherAnions = | OtherAnions =
| OtherCations = ], ] | OtherCations = ], ]
| OtherFunctn = | OtherFunction =
| OtherFunction_label =
| Function =
| OtherCpds = ]}} | OtherCompounds = ]}}
}} }}


'''Copper(II) aspirinate''' is an ] ] of copper(II) cations (Cu<sup>2+</sup>). It is used to treat ]. '''Copper(II) aspirinate''' is an ] ] of copper(II) cations (Cu<sup>2+</sup>). It is used to treat ].

]


==Preparation== ==Preparation==
Copper aspirinate can be prepared by several methods. In one route of preparation, an excess of acetylsalicylic acid is dissolved in ] ]. ] is not suitable for this purpose, because it will ] acetylsalicylic acid (''ASA'') into ] and ]. Copper aspirinate can be prepared by several methods. In one route of preparation, an excess of ] is dissolved in ] ]. ] is not suitable for this purpose, because it will ] acetylsalicylic acid (''ASA'') into ] and ].


::2 HC<sub>9</sub>H<sub>7</sub>O<sub>4</sub> + Na<sub>2</sub>CO<sub>3</sub> → 2 NaC<sub>9</sub>H<sub>7</sub>O<sub>4</sub> + CO<sub>2</sub>↑ + H<sub>2</sub>O ::2 HC<sub>9</sub>H<sub>7</sub>O<sub>4</sub> + Na<sub>2</sub>CO<sub>3</sub> → 2 NaC<sub>9</sub>H<sub>7</sub>O<sub>4</sub> + CO<sub>2</sub>↑ + H<sub>2</sub>O


The resulting solution is then filtered to remove any undissolved acetylsalicylic acid and is mixed with a solution containing ] cations (] 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. The resulting solution is then filtered to remove any undissolved acetylsalicylic acid and is mixed with a solution containing ] cations (] 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 NaC<sub>9</sub>H<sub>7</sub>O<sub>4</sub> + 2 CuSO<sub>4</sub> → C<sub>36</sub>H<sub>28</sub>Cu<sub>2</sub>O<sub>16</sub>↓ + 2 Na<sub>2</sub>SO<sub>4</sub> ::4 NaC<sub>9</sub>H<sub>7</sub>O<sub>4</sub> + 2 CuSO<sub>4</sub> → C<sub>36</sub>H<sub>28</sub>Cu<sub>2</sub>O<sub>16</sub>↓ + 2 Na<sub>2</sub>SO<sub>4</sub>


==Medicinal Use== ==Medicinal use==
Copper aspirinate has been proven effective as a treatment for ].<ref>{{cite web | last = | first = | title = Rheumatoid Arthritis (RA) | publisher = Copper Development Association | date = June 2000 | url = http://www.copper.org/innovations/2000/06/medicine-chest.html }}</ref> Copper aspirinate has been proven effective as a treatment for ].<ref>{{cite web | title = Rheumatoid Arthritis (RA) | publisher = Copper Development Association | date = June 2000 | url = http://www.copper.org/innovations/2000/06/medicine-chest.html | access-date = 2007-03-05 | archive-url = https://web.archive.org/web/20070202230851/http://www.copper.org/innovations/2000/06/medicine-chest.html | archive-date = 2007-02-02 | url-status = dead }}</ref> A pharmacokinetic study in healthy human volunteers supports its enhanced efficacy as compared with aspirin.<ref>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</ref>
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.<ref>{{cite journal | title = Potential Application of Copper Aspirinate in Preventing and Treating Thromboembolic Diseases |journal =Met Based Drugs. | publisher = Hindawi Publishing Corporation | year = 1998 |volume = 5 |issue = 3 |pages = 123–126 |doi = 10.1155/MBD.1998.123 |url = http://www.copper.org/innovations/2000/06/medicine-chest.html |author = Weiping Liu,corresponding author1 Huizhou Xiong, Yikun Yang Ling Li, Zhiqiang Shen, and Zhihe Chen | pmid = 18475833 | pmc = 2365110 }}</ref> 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.<ref>{{cite journal |title = Potential Application of Copper Aspirinate in Preventing and Treating Thromboembolic Diseases |journal = Metal-Based Drugs|year = 1998 |volume = 5 |issue = 3 |pages = 123–126 |doi = 10.1155/MBD.1998.123 |author = Weiping Liu,corresponding author1 Huizhou Xiong, Yikun Yang Ling Li, Zhiqiang Shen, and Zhihe Chen |pmid = 18475833 |pmc = 2365110 |doi-access = free}}</ref>


==Other uses== ==Other uses==
The use of copper aspirinate as a pigment in ] and ] has also been investigated.<ref>{{cite journal | last = Allan | first = J R | coauthors = A Renton, W E Smith, D L Gerrard, J Birnie | title = 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 | journal = Eur. Polym. J. | volume = 27 | issue = 7 | pages = 669–672 | publisher = | year = 1991 | url = | accessdate = | doi = 10.1016/0014-3057(91)90155-H }}</ref> The use of copper aspirinate as a pigment in ] and ] has also been investigated.<ref>{{cite journal | last = Allan | first = J R |author2=A Renton |author3=W E Smith |author4=D L Gerrard |author5=J Birnie | title = 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 | journal = Eur. Polym. J. | volume = 27 | issue = 7 | pages = 669–672 | year = 1991 | doi = 10.1016/0014-3057(91)90155-H | bibcode = 1991EurPJ..27..669A }}</ref>


==External links== ==External links==
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{{DEFAULTSORT:Copper Aspirinate}} {{DEFAULTSORT:Copper Aspirinate}}
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