View source for 2,2'-Azobis(2-amidinopropane) dihydrochloride

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| ImageFile =2,2'-Azobis(2-amidinopropane) dihydrochloride.svg
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| IUPACName = (1Z,1'Z)-2,2'-[(E)-1,2-Diazenediyl]bis(2-methylpropanimidamide) dihydrochloride
| OtherNames = AAPH; AMPA; 2,2'-Azobisisobutyramidinium chloride
|Section1={{Chembox Identifiers
| CASNo = 2997-92-4
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7381JDR72F
| ChemSpiderID = 68821
| PubChem =84924
| SMILES = Cl.Cl.[N@H]=C(N)C(/N=N/C(C(=[N@H])N)(C)C)(C)C
| StdInChI = 1S/C8H18N6.2ClH/c1-7(2,5(9)10)13-14-8(3,4)6(11)12;;/h1-4H3,(H3,9,10)(H3,11,12);2*1H/b14-13+
| StdInChIKey = LXEKPEMOWBOYRF-QDBORUFSSA-N
}}
|Section2={{Chembox Properties
| Formula =
| C=8 | H=20 | Cl=2 | N=6
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|Section3={{Chembox Hazards
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'''2,2'-Azobis(2-amidinopropane) dihydrochloride''' (abbreviated AAPH or AMPA) is a chemical compound used to study the chemistry of the [[oxidation]] of [[drug]]s.<ref>{{Cite journal | last1 = Betigeri | first1 = S. | last2 = Thakur | first2 = A. | last3 = Raghavan | first3 = K. | doi = 10.1007/s11095-004-1199-x | title = Use of 2,2?-Azobis(2-Amidinopropane) Dihydrochloride as a Reagent Tool for Evaluation of Oxidative Stability of Drugs | journal = Pharmaceutical Research | volume = 22 | issue = 2 | pages = 310–317 | year = 2005 | pmid =  15783080| s2cid = 38031845 }}</ref>
It is a [[free radical]]-generating [[azo compound]]. It is gaining prominence as a model oxidant in [[small molecule]] and [[protein]] therapeutics for its ability to initiate oxidation reactions via both nucleophilic and free radical mechanisms.<ref>{{Cite journal | last1 = Werber | first1 = J. | last2 = Wang | first2 = Y. J. | last3 = Milligan | first3 = M. | last4 = Li | first4 = X. | last5 = Ji | first5 = J. A. | title = Analysis of 2,2′-azobis (2-amidinopropane) dihydrochloride degradation and hydrolysis in aqueous solutions | doi = 10.1002/jps.22578 | journal = Journal of Pharmaceutical Sciences | volume = 100 | issue = 8 | pages = 3307–3315 | year = 2011 | pmid =  21560126}}</ref>
2,2′-azobis (2-amidinopropane) dihydrochloride has been used in experiments on [[linoleic acid]] subjected to induced oxidation with different combinations of binary mixtures of [[natural phenol]]ics. The experiments show that some binary mixtures can lead to a [[synergy|synergetic]] [[Antioxidant effect of natural phenols|antioxidant effect]] while other mixtures lead to an [[Antagonism (chemistry)|antagonistic]] effect.<ref>Antioxidant activity of phenolic compounds in 2,2′-azobis (2-amidinopropane) dihydrochloride (AAPH)-induced oxidation: Synergistic and antagonistic effects. M. N. Peyrat-Maillard, M. E. Cuvelier and C. Berset, Journal of the American Oil Chemists' Society, 2003, Volume 80, Number 10, pages 1007-1012, {{doi|10.1007/s11746-003-0812-z}}</ref>
== References ==
{{Reflist}}
{{DEFAULTSORT:Azobis(2-amidinopropane) dihydrochloride, 2,2'-}}
[[Category:Azo compounds]]
[[Category:Amidines]]