Postmortem Identification and Quantitation of 2,5-Dimethoxy-4-n-propylthiophenethylamine Using GC-MSD and GC-NPD

Abstract

2,5-Dimethoxy-4-n-propylthiophenethylamine (2C-T-7) has structural and pharmacodynamic similarities to methylenedioxymethamphetamine (MDMA). This compound was initially identified from a routine screening procedure in postmortem urine from a 20-year-old male that died in a local emergency room after reportedly insufflating 35 mg. This report describes the development of a quantitative method for 2C-T-7. A number of method parameters were studied including internal standard selection, liquid-liquid extraction scheme, and drug stability in preserved refrigerated blood. The adopted method for blood and urine involves the addition of trimethoxyamphetamine (TMA) as internal standard, alkalinization with ammonium hydroxide, and liquid-liquid extraction with n-chlorobutane. To facilitate recovery from liver, a 1:4 aqueous homogenate was pretreated with dilute perchloric acid, centrifuged, and the supernatant was extracted as previously described. In each case, 0.1% hydrochloric acid in methanol was added during the final concentration step to prevent loss of drug caused by evaporation. Samples were analyzed by gas chromatography with nitrogen-phosphorus detection (GC-NPD) and electron ionization GC-mass spectrometry (MS) utilizing selected ion monitoring. For the GC-MS analysis, the characteristic ions monitored for 2C-T-7 were m/z 226, 255, and 183 and for TMA, m/z 182. The limits of detection and quantitation in blood were 6.0 and 15.6 ng/mL, respectively, by both GC-NPD and GC-MS. The results from the postmortem case were as follows: heart blood, 57 ng/mL; femoral blood, 100 ng/mL; urine, 1120 ng/mL; and liver, 854 ng/g.

Analysis of Phenethylamines and Tryptamines in Designer Drugs Using Gas Chromatographymass Spectrometry

“…1) as the analytical targets because in our institute we frequently experienced the drug cases which they were determined using mass spectrometry (MS) and nuclear magnetic resonance (NMR). These were as follows: 3,4,5-trimethoxyamphetamine (TMA) and 4-bromo-2,5-dimethoxyphenethylamine (2C-B), which are phenethylamine hallucinogens and have been recently designated as narcotic drugs; and 2,4,5-trimethoxyamphetamine (TMA-2), 4-iodo-2,5-dimethoxyphenethylamine (2C-I), 2,5-dimethoxy-4-ethylthiophenethylamine (2CT-2), 7) 2,5-dimethoxy-4-propylthiophenethylamine (2CT-7), [7][8][9] and four designer tryptamines that are their analogs with similar hallucinatory effects. The four designer tryptamines 10,11) are 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT), α-methyltryptamine (AMT), N-isopropyl-5-methoxy-N-methyltryptamine (5-MeO-MIPT), and N,N-diisopropyl-5-methoxytryptamine (5-MeO-DIPT).…”

Screening for and validated quantification of phenethylamine‐type designer drugs and mescaline in human blood plasma by gas chromatography/mass spectrometry

“…It must be stressed that criteria for this validation parameter, that is, ratio of means (refrigerator vs control samples) within 90 to 110%, and 90% CI for refrigerator samples within 80 to 120% of control mean, were fulfilled for all substances at both concentrations. From the results of the stability study published by Curtis et al, 31 2C-T-7 appears to be stable for approximately 70 days in sodium fluoride-preserved blood when stored at 4°C.…”

“…3,7,8,31 -34,36 -45 Gas chromatographic/mass spectrometric (GC/MS) procedures have been published for detection of 2C-B, 7,8,32 -34,42 2C-T-2, 36,38,43 2C-T-7, 8,37 mescaline, 44 and/or their metabolites in urine. Only a few publications report GC/MS analysis of 2C-B, 8 2C-T-7, 8,31 and mescaline 45 in plasma and/or postmortem blood. However, no assays have been published for simultaneous screening and/or validated quantification of phenethylamine designer drugs in human blood plasma.…”

New Synthetic Drugs in Addictovigilance

“…In the absence of a specific antidote, the care provision for 2C-X or 25X-NBOMe intoxication is merely symptomatic, involving in particular sedation using benzodiazepines as the first line treatment. [22,27,28,[32][33][34][35] Intoxications can be severe, and deaths have been related to 2C-T-7 [23,36] and 2C-E. [37] Concerning 25X-NBOMe, several deaths have also been reported, particularly involving 25I-NBOMe, this being so despite the recent appearance of these drugs on the market. World Health Organization (WHO) has reported over twenty deaths as a result of using 25X-NBOMe, the majority being attributed to acute overdose.…”