Published: Journal of Analytical Toxicology, ISSN 0146-4760, Volume 30, Issue 6, July/August 2006, pp.395-399

TECHNICAL NOTE: Conversion of Sertraline to N-Methyl Sertraline in Embalming Fluid: A Forensic Implication
Ramagiri Suma and P.K. Sai Prakash
Osmania University, Department of Chemistry, Hyderabad-500007, India

Zoloft (sertraline hydrochloride) is one of the antidepressant medications used to treat depression, obsessive-compulsive disorder, and social anxiety disorder. The practice of embalming a cadaver is common, yet it may create problems for forensic toxicologists if the case was not previously suspected to involve drug overdose. According to the Eschweiler–Clarke reaction, drugs containing a secondary amine group react with formaldehyde to give N-methyl derivatives. Sertraline has a secondary amine group; therefore, we predicted that it may react with formalin to give N-methyl derivatives. The stability of sertraline in formalin solution was studied at three different concentrations (5%, 10%, and 20%) and at three different pHs (3.0, 7.0, and 9.5) for a period of 30 days. Setraline and its degraded products were extracted by liquid–liquid extraction using chloroform, and the concentrated extracts were analyzed by gas chromatography– mass spectrometry using electron impact ionization mode. The rate of conversion is rapid at higher pH. Sertraline was totally converted to the N-methyl derivative after 30 days in 10% and 20% formalin solutions at neutral and basic conditions. Therefore, forensic toxicologists should be cautious when performing a death investigation if formalin solution is the only sample available for analysis. This work shows that analysis for parent drug or its N-methyl derivative may provide data that will reduce the likelihood of false negatives.

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