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Does Para-chloroaniline Really Form after Mixing Sodium Hypochlorite and Chlorhexidine?

Published:January 29, 2016DOI:https://doi.org/10.1016/j.joen.2015.12.024

      Highlights

      • Precipitation occurring as a result of mixing sodium hypochlorite and chlorhexidine digluconate does not contain para-chloroaniline.
      • Mass spectrometry may not be valid to detect availability of para-chloroaniline.

      Abstract

      Introduction

      Mixing sodium hypochlorite (NaOCl) with chlorhexidine (CHX) forms a brown-colored precipitate. Previous studies are not in agreement whether this precipitate contains para-chloroaniline (PCA). Tests used for analysis may demonstrate different outcomes. Purpose of this study was to determine whether PCA is formed through the reaction of mixing NaOCl and CHX by using high performance liquid chromatography, proton nuclear magnetic resonance spectroscopy, gas chromatography, thin layer chromatography, infrared spectroscopy, and gas chromatography/mass spectrometry.

      Methods

      To obtain a brown precipitate, 4.99% NaOCl was mixed with 2.0% CHX. This brown precipitate was analyzed and compared with signals obtained from commercially available 4.99% NaOCl, 2% solutions, and 98% PCA in powder form.

      Results

      Chromatographic and spectroscopic analyses showed that brown precipitate does not contain free PCA.

      Conclusions

      This study will be a cutoff proof for the argument on PCA formation from reaction of CHX and NaOCl.

      Key Words

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      References

        • Moorer W.R.
        • Wesselink P.R.
        Factors promoting the tissue dissolving capability of sodium hypochlorite.
        Int Endod J. 1982; 15: 187-196
        • Hasselgren G.
        • Olsson B.
        • Cvek M.
        Effects of calcium hydroxide and sodium hypochlorite on the dissolution of necrotic porcine muscle tissue.
        J Endod. 1988; 14: 125-127
        • Clarkson R.M.
        • Kidd B.
        • Evans G.E.
        • et al.
        The effect of surfactant on the dissolution of porcine pulpal tissue by sodium hypochlorite solutions.
        J Endod. 2012; 38: 1257-1260
        • Rosenfeld E.F.
        • James G.A.
        • Burch B.S.
        Vital pulp tissue response to sodium hypochlorite.
        J Endod. 1978; 4: 140-146
        • Sassone L.M.
        • Fidel R.A.
        • Murad C.F.
        • et al.
        Antimicrobial activity of sodium hypochlorite and chlorhexidine by two different tests.
        Aust Endod J. 2008; 34: 19-24
        • Becking A.G.
        Complications in the use of sodium hypochlorite during endodontic treatment: report of three cases.
        Oral Surg Oral Med Oral Pathol. 1991; 71: 346-348
        • Ehrich D.G.
        • Brian Jr., J.D.
        • Walker W.A.
        Sodium hypochlorite accident: inadvertent injection into the maxillary sinus.
        J Endod. 1993; 19: 180-182
        • Ohara P.
        • Torabinejad M.
        • Kettering J.D.
        Antibacterial effects of various endodontic irrigants on selected anaerobic bacteria.
        Endod Dent Traumatol. 1993; 9: 95-100
        • Naenni N.
        • Thoma K.
        • Zehnder M.
        Soft tissue dissolution capacity of currently used and potential endodontic irrigants.
        J Endod. 2004; 30: 785-787
        • Kuruvilla J.R.
        • Kamath M.P.
        Antimicrobial activity of 2.5% sodium hypochlorite and 0.2% chlorhexidine gluconate separately and combined, as endodontic irrigants.
        J Endod. 1998; 24: 472-476
        • Vianna M.E.
        • Gomes B.P.
        • Berber V.B.
        • et al.
        In vitro evaluation of the antimicrobial activity of chlorhexidine and sodium hypochlorite.
        Oral Surg Oral Med Oral Pathol Oral Radiol Endod. 2004; 97: 79-84
        • Zehnder M.
        Root canal irrigants.
        J Endod. 2006; 32: 389-398
        • Bui T.B.
        • Baumgartner J.C.
        • Mitchell J.C.
        Evaluation of the interaction between sodium hypochlorite and chlorhexidine gluconate and its effect on root dentin.
        J Endod. 2008; 34: 181-185
        • Basrani B.R.
        • Manek S.
        • Sodhi R.N.
        • et al.
        Interaction between sodium hypochlorite and chlorhexidine gluconate.
        J Endod. 2007; 33: 966-969
        • Basrani B.R.
        • Manek S.
        • Mathers D.
        • et al.
        Determination of 4-chloroaniline and its derivatives formed in the interaction of sodium hypochlorite and chlorhexidine by using gas chromatography.
        J Endod. 2010; 36: 312-314
        • Kolosowski K.P.
        • Sodhi R.N.
        • Kishen A.
        • et al.
        Qualitative analysis of precipitate formation on the surface and in the tubules of dentin irrigated with sodium hypochlorite and a final rinse of chlorhexidine or QMiX.
        J Endod. 2014; 40: 2036-2040
        • Mortenson D.
        • Sadilek M.
        • Flake N.M.
        • et al.
        The effect of using an alternative irrigant between sodium hypochlorite and chlorhexidine to prevent the formation of para-chloroaniline within the root canal system.
        Int Endod J. 2012; 45: 878-882
        • Thomas J.E.
        • Sem D.S.
        An in vitro spectroscopic analysis to determine whether para-chloroaniline is produced from mixing sodium hypochlorite and chlorhexidine.
        J Endod. 2010; 36: 315-317
        • Marchesan M.A.
        • Pasternak Júnior B.
        • Afonso M.M.
        • et al.
        Chemical analysis of the flocculate formed by the association of sodium hypochlorite and chlorhexidine.
        Oral Surg Oral Med Oral Pathol Oral Radiol Endod. 2007; 103: e103-e105
        • Basrani B.R.
        • Manek S.
        • Fillery E.
        Using diazotization to characterize the effect of heat or sodium hypochlorite on 2.0% chlorhexidine.
        J Endod. 2009; 35: 1296-1299
        • Krishnamurthy S.
        • Sudhakaran S.
        Evaluation and prevention of the precipitate formed on interaction between sodium hypochlorite and chlorhexidine.
        J Endod. 2010; 36: 1154-1157
        • Ballal N.V.
        • Moorkoth S.
        • Mala K.
        • et al.
        Evaluation of chemical interactions of maleic acid with sodium hypochlorite and chlorhexidine gluconate.
        J Endod. 2011; 37: 1402-1405
        • Arslan H.
        • Uygun A.D.
        • Keskin A.
        • et al.
        Evaluation of orange-brown precipitate formed in root canals after irrigation with chlorhexidine and QMix and spectroscopic analysis of precipitates produced by a mixture of chlorhexidine/NaOCl and QMix/NaOCl.
        Int Endod J. 2015; 48: 1199-1203
        • Boehncke A.
        • Kielhorn J.
        • Koennecker G.
        • et al.
        Concise International Chemical Assessment Document 48: 4-Chloroaniline.
        World Health Organization, Geneva, Switzerland2003
        • Chhabra R.S.
        • Huff J.E.
        • Haseman J.K.
        • et al.
        Carcinogenicity of p-chloroaniline in rats and mice.
        Food Chem Toxicol. 1991; 29: 119-124
        • Ramsay D.H.
        • Harvey C.C.
        Marking ink poisoning: an outbreak of methaemoglobin cyanosis in newborn babies.
        Lancet. 1959; 1: 910-912
        • Messmer A.S.
        • Nickel C.H.
        • Bareiss D.
        P-chloroaniline poisoning causing methemoglobinemia: a case report and review of the literature.
        Case Rep Emerg Med. 2015; 2015: 208732
        • Kulkarni B.S.
        • Acharya V.N.
        • Khanna R.M.
        • et al.
        Methemoglobinemia due to nitro-aniline intoxication: review of the literature with a report of 9 cases.
        J Postgrad Med. 1969; 15: 192-200
        • Below H.
        • Lehan N.
        • Kramer A.
        HPLC determination of the antiseptic agent chlorhexidine and its degradation products 4-chloroaniline and 1-chloro-4-nitrobenzene in serum and urine.
        Microchimica Acta. 2004; 146: 129-135
        • Havlikova L.
        • Matysova L.
        • Novakova L.
        • et al.
        HPLC determination of chlorhexidine gluconate and p-chloroaniline in topical ointment.
        J Pharm Biomed Anal. 2007; 43: 1169-1173
        • Harwood L.M.
        • Moody C.J.
        Experimental Organic Chemistry: Principles and Practice.
        Blackwell Scientific, Oxford1989
        • Vogel A.I.
        • Furniss B.S.
        • Vogel A.I.
        Vogel's Textbook of Practical Organic Chemistry.
        Wiley, New York1989
        • Ramachandran K.N.
        • Gupta V.K.
        New analytical technique for the simultaneous determination of aromatic amines.
        Fresenius J Anal Chem. 1993; 346: 457-458