A General Screening and Confirmation Approach to the Analysis of Designer Tryptamines and Phenethylamines in Blood and Urine Using GC-EI-MS and HPLC-Electrospray-MS

Abstract

Recent additions of designer tryptamines and phenethylamines to the Drug Enforcement Administration's schedule of controlled substances necessitate analytical procedures for their detection and quantitation. As specific immunoassays are not currently available and cross-reactivities with existing assays are unknown, a screening method based on gas chromatography-mass spectrometry was developed. The method was capable of measuring the pentafluoropropionic derivatives of a-methyltryptamine (AMT), N,N-dimethyltryptamine (DMT), 4-bromo-2,5-dimethoxy-beta-phenethylamine (2CB), N,N-dipropyltryptamine (DPT), 2,5-dimethyl-4-N-propylthio-beta-phenethylamine (2C-T-7), and 5-methoxy-N,N-diisopropyltryptamine (5-MeO-DiPT). Separation was optimized to allow tentative identification of metabolites, which display common electron impact ionization fragmentation patterns. The screening method gave limits of detection between 5 and 10 ng/mL and demonstrated linearity between 50 and 1000 ng/mL. The method was successfully applied to blood and urine samples in suspected AMT intoxications. Confirmation of 5-MeO-DiPT in one of the subjects' urine was achieved using liquid chromatography-mass spectrometry (LC-MS). Quantitation by selected ion monitoring (SIM) yielded a urinary concentration of 229 ng/mL. The method was linear from 25 to 1500 ng/mL with a correlation coefficient of 0.995. The limit of detection was 5 ng/mL in urine on the LC-MS. Two additional peaks were observed and presumed to be metabolic products reported previously as 5-methoxy-N-isopropyltryptamine (5-MeO-iPT) and 5-methoxy-N,N-diisopropyltryptamine-N'-oxide (5-MeO-DiPT-N-oxide).

Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class

“…The class of N,N-dialkylated tryptamines has been a constant element of interest within the context of new psychoactive substances (NPS) (Meatherall and Sharma, 2003;Smolinske et al, 2005;Tanaka et al, 2006;Vorce and Sklerov, 2004;Wilson et al, 2005). Another newer tryptamine, 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT), was associated with a fatal poisoning (Elliott and Evans, 2014).…”

Simultaneous Separation and Detection of 18 Phenethylamine/Tryptamine Derivatives by Liquid Chromatography–UV Absorption and –Electrospray Ionization Mass Spectrometry

“…[7][8][9][10][11][12][13][14][15][16][17] However, the major ionization source used in GC/MS Loved) and TiHKAL (Tryptamines i Have Known and Loved), is electron impact (EI) and, in many cases, acquiring parent ions respectively. 1,2 Unfortunately, these compounds have been abused of the analytes is a difficult task.…”

Identification and quantitative determination of 5-methoxy-N,N-di-n-propyltryptamine in urine by isotope dilution gas chromatography-mass spectrometry

“…Recently, illicit drugs have become easily obtainable all over the world through the Internet, and acute poisoning caused by such drugs occurs frequently. Tryptamine derivatives are often used and some poisoning cases have been reported [2][3][4][5][6]. There are also reports of problems arising from mislabeling of ingredients in "2C-C", "2CT-21" and "4-acetoxy-DIPT" [7,8].…”