Conversion of Sertraline to N-Methyl Sertraline in Embalming Fluid: A Forensic Implication

• Published in: Journal of analytical toxicology Vol. 30; no. 6; pp. 395 - 399
• Main Authors: Suma, Ramagiri, Prakash, P.K. Sai
• Format: Journal Article
• Language: English
• Published: Niles, IL Oxford University Press 01.07.2006; Preston
• Subjects: Antidepressive Agents - analysis; Antidepressive Agents - chemistry; Antidepressive Agents - toxicity; Biological and medical sciences; Drug Overdose - diagnosis; Drug Stability; Embalming - methods; Forensic Medicine - methods; Formaldehyde - chemistry; Gas Chromatography-Mass Spectrometry; Hydrogen-Ion Concentration; Medical sciences; Neuropharmacology; Pharmacology. Drug treatments; Psychoanaleptics: cns stimulant, antidepressant agent, nootropic agent, mood stabilizer..., (alzheimer disease); Psychology. Psychoanalysis. Psychiatry; Psychopharmacology; Reproducibility of Results; Sertraline - analogs & derivatives; Sertraline - analysis; Sertraline - chemistry; Sertraline - toxicity; Time Factors; Biological fluid; Chemical analysis; Psychotropic; Embalming; Chemical stability; Forensic aspect; Reuptake inhibitor; Solvent extraction; Formaldehyde; Sample preparation; pH; Antidepressant agent; Quantitative analysis; Serotonin; Liquid liquid extraction; Coupled method; Reaction product; Postmortem; Aldehyde; Autopsy material; Sertraline; Gas chromatography; Medium effect; Concentration effect; Neurotransmitter; Kinetics; Methylation; Mass spectrometry
• ISSN: 0146-4760; 1945-2403
• DOI: 10.1093/jat/30.6.395

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 drugor its N-methyl derivative may provide data that will reduce the likelihood of false negatives.